fix(node): better detection for when to surface node resolution errors (#24653)

35 files changed, 676 insertions, 517 deletions

diff --git a/cli/module_loader.rs b/cli/module_loader.rs
index 4254375e5..2e047d36d 100644
--- a/cli/module_loader.rs
+++ b/cli/module_loader.rs
@@ -446,15 +446,14 @@ impl<TGraphContainer: ModuleGraphContainer>
     specifier: &str,
     referrer: &ModuleSpecifier,
   ) -> Result<ModuleSpecifier, AnyError> {
-    if let Some(result) = self.shared.node_resolver.resolve_if_in_npm_package(
-      specifier,
-      referrer,
-      NodeResolutionMode::Execution,
-    ) {
-      return match result? {
-        Some(res) => Ok(res.into_url()),
-        None => Err(generic_error("not found")),
-      };
+    if self.shared.node_resolver.in_npm_package(referrer) {
+      return Ok(
+        self
+          .shared
+          .node_resolver
+          .resolve(specifier, referrer, NodeResolutionMode::Execution)?
+          .into_url(),
+      );
     }
 
     let graph = self.graph_container.graph();
diff --git a/cli/npm/byonm.rs b/cli/npm/byonm.rs
index f776b79c1..d10bb6b2a 100644
--- a/cli/npm/byonm.rs
+++ b/cli/npm/byonm.rs
@@ -12,7 +12,8 @@ use deno_core::serde_json;
 use deno_package_json::PackageJsonDepValue;
 use deno_runtime::deno_fs::FileSystem;
 use deno_runtime::deno_node::errors::PackageFolderResolveError;
-use deno_runtime::deno_node::errors::PackageFolderResolveErrorKind;
+use deno_runtime::deno_node::errors::PackageFolderResolveIoError;
+use deno_runtime::deno_node::errors::PackageNotFoundError;
 use deno_runtime::deno_node::load_pkg_json;
 use deno_runtime::deno_node::NodePermissions;
 use deno_runtime::deno_node::NpmResolver;
@@ -198,7 +199,7 @@ impl NpmResolver for ByonmCliNpmResolver {
       }
 
       Err(
-        PackageFolderResolveErrorKind::NotFoundPackage {
+        PackageNotFoundError {
           package_name: name.to_string(),
           referrer: referrer.clone(),
           referrer_extra: None,
@@ -209,7 +210,7 @@ impl NpmResolver for ByonmCliNpmResolver {
 
     let path = inner(&*self.fs, name, referrer)?;
     self.fs.realpath_sync(&path).map_err(|err| {
-      PackageFolderResolveErrorKind::Io {
+      PackageFolderResolveIoError {
         package_name: name.to_string(),
         referrer: referrer.clone(),
         source: err.into_io_error(),
diff --git a/cli/npm/managed/mod.rs b/cli/npm/managed/mod.rs
index a18ad4d7f..602733cab 100644
--- a/cli/npm/managed/mod.rs
+++ b/cli/npm/managed/mod.rs
@@ -21,7 +21,7 @@ use deno_npm::NpmResolutionPackage;
 use deno_npm::NpmSystemInfo;
 use deno_runtime::deno_fs::FileSystem;
 use deno_runtime::deno_node::errors::PackageFolderResolveError;
-use deno_runtime::deno_node::errors::PackageFolderResolveErrorKind;
+use deno_runtime::deno_node::errors::PackageFolderResolveIoError;
 use deno_runtime::deno_node::NodePermissions;
 use deno_runtime::deno_node::NpmResolver;
 use deno_semver::package::PackageNv;
@@ -549,7 +549,7 @@ impl NpmResolver for ManagedCliNpmResolver {
       .resolve_package_folder_from_package(name, referrer)?;
     let path =
       canonicalize_path_maybe_not_exists_with_fs(&path, self.fs.as_ref())
-        .map_err(|err| PackageFolderResolveErrorKind::Io {
+        .map_err(|err| PackageFolderResolveIoError {
           package_name: name.to_string(),
           referrer: referrer.clone(),
           source: err,
diff --git a/cli/npm/managed/resolvers/global.rs b/cli/npm/managed/resolvers/global.rs
index d16fe7cd0..e7a57fc23 100644
--- a/cli/npm/managed/resolvers/global.rs
+++ b/cli/npm/managed/resolvers/global.rs
@@ -15,7 +15,8 @@ use deno_npm::NpmPackageId;
 use deno_npm::NpmSystemInfo;
 use deno_runtime::deno_fs::FileSystem;
 use deno_runtime::deno_node::errors::PackageFolderResolveError;
-use deno_runtime::deno_node::errors::PackageFolderResolveErrorKind;
+use deno_runtime::deno_node::errors::PackageNotFoundError;
+use deno_runtime::deno_node::errors::ReferrerNotFoundError;
 use deno_runtime::deno_node::NodePermissions;
 
 use super::super::cache::NpmCache;
@@ -84,7 +85,7 @@ impl NpmPackageFsResolver for GlobalNpmPackageResolver {
       .resolve_package_folder_id_from_specifier(referrer)
     else {
       return Err(
-        PackageFolderResolveErrorKind::NotFoundReferrer {
+        ReferrerNotFoundError {
           referrer: referrer.clone(),
           referrer_extra: None,
         }
@@ -98,7 +99,7 @@ impl NpmPackageFsResolver for GlobalNpmPackageResolver {
       Ok(pkg) => match self.maybe_package_folder(&pkg.id) {
         Some(folder) => Ok(folder),
         None => Err(
-          PackageFolderResolveErrorKind::NotFoundPackage {
+          PackageNotFoundError {
             package_name: name.to_string(),
             referrer: referrer.clone(),
             referrer_extra: Some(format!(
@@ -112,7 +113,7 @@ impl NpmPackageFsResolver for GlobalNpmPackageResolver {
       },
       Err(err) => match *err {
         PackageNotFoundFromReferrerError::Referrer(cache_folder_id) => Err(
-          PackageFolderResolveErrorKind::NotFoundReferrer {
+          ReferrerNotFoundError {
             referrer: referrer.clone(),
             referrer_extra: Some(cache_folder_id.to_string()),
           }
@@ -122,7 +123,7 @@ impl NpmPackageFsResolver for GlobalNpmPackageResolver {
           name,
           referrer: cache_folder_id_referrer,
         } => Err(
-          PackageFolderResolveErrorKind::NotFoundPackage {
+          PackageNotFoundError {
             package_name: name,
             referrer: referrer.clone(),
             referrer_extra: Some(cache_folder_id_referrer.to_string()),
diff --git a/cli/npm/managed/resolvers/local.rs b/cli/npm/managed/resolvers/local.rs
index 90a17b157..cda78548b 100644
--- a/cli/npm/managed/resolvers/local.rs
+++ b/cli/npm/managed/resolvers/local.rs
@@ -33,7 +33,9 @@ use deno_npm::NpmResolutionPackage;
 use deno_npm::NpmSystemInfo;
 use deno_runtime::deno_fs;
 use deno_runtime::deno_node::errors::PackageFolderResolveError;
-use deno_runtime::deno_node::errors::PackageFolderResolveErrorKind;
+use deno_runtime::deno_node::errors::PackageFolderResolveIoError;
+use deno_runtime::deno_node::errors::PackageNotFoundError;
+use deno_runtime::deno_node::errors::ReferrerNotFoundError;
 use deno_runtime::deno_node::NodePermissions;
 use deno_semver::package::PackageNv;
 use serde::Deserialize;
@@ -185,14 +187,14 @@ impl NpmPackageFsResolver for LocalNpmPackageResolver {
   ) -> Result<PathBuf, PackageFolderResolveError> {
     let maybe_local_path = self
       .resolve_folder_for_specifier(referrer)
-      .map_err(|err| PackageFolderResolveErrorKind::Io {
+      .map_err(|err| PackageFolderResolveIoError {
         package_name: name.to_string(),
         referrer: referrer.clone(),
         source: err,
       })?;
     let Some(local_path) = maybe_local_path else {
       return Err(
-        PackageFolderResolveErrorKind::NotFoundReferrer {
+        ReferrerNotFoundError {
           referrer: referrer.clone(),
           referrer_extra: None,
         }
@@ -220,7 +222,7 @@ impl NpmPackageFsResolver for LocalNpmPackageResolver {
     }
 
     Err(
-      PackageFolderResolveErrorKind::NotFoundPackage {
+      PackageNotFoundError {
         package_name: name.to_string(),
         referrer: referrer.clone(),
         referrer_extra: None,
diff --git a/cli/resolver.rs b/cli/resolver.rs
index c332878a2..c1bb8a0a5 100644
--- a/cli/resolver.rs
+++ b/cli/resolver.rs
@@ -25,15 +25,17 @@ use deno_runtime::deno_fs;
 use deno_runtime::deno_fs::FileSystem;
 use deno_runtime::deno_node::errors::ClosestPkgJsonError;
 use deno_runtime::deno_node::errors::NodeResolveError;
-use deno_runtime::deno_node::errors::ResolvePkgSubpathFromDenoModuleError;
+use deno_runtime::deno_node::errors::NodeResolveErrorKind;
+use deno_runtime::deno_node::errors::PackageFolderResolveErrorKind;
+use deno_runtime::deno_node::errors::PackageFolderResolveIoError;
+use deno_runtime::deno_node::errors::PackageNotFoundError;
+use deno_runtime::deno_node::errors::PackageResolveErrorKind;
 use deno_runtime::deno_node::errors::UrlToNodeResolutionError;
 use deno_runtime::deno_node::is_builtin_node_module;
-use deno_runtime::deno_node::parse_npm_pkg_name;
 use deno_runtime::deno_node::NodeModuleKind;
 use deno_runtime::deno_node::NodeResolution;
 use deno_runtime::deno_node::NodeResolutionMode;
 use deno_runtime::deno_node::NodeResolver;
-use deno_runtime::deno_node::NpmResolver as DenoNodeNpmResolver;
 use deno_runtime::deno_node::PackageJson;
 use deno_runtime::fs_util::specifier_to_file_path;
 use deno_semver::npm::NpmPackageReqReference;
@@ -47,7 +49,6 @@ use crate::args::JsxImportSourceConfig;
 use crate::args::DENO_DISABLE_PEDANTIC_NODE_WARNINGS;
 use crate::colors;
 use crate::node::CliNodeCodeTranslator;
-use crate::npm::ByonmCliNpmResolver;
 use crate::npm::CliNpmResolver;
 use crate::npm::InnerCliNpmResolverRef;
 use crate::util::sync::AtomicFlag;
@@ -102,17 +103,77 @@ impl CliNodeResolver {
     self.node_resolver.get_closest_package_json(referrer)
   }
 
-  pub fn resolve_if_in_npm_package(
+  pub fn resolve_if_for_npm_pkg(
     &self,
     specifier: &str,
     referrer: &ModuleSpecifier,
     mode: NodeResolutionMode,
-  ) -> Option<Result<Option<NodeResolution>, NodeResolveError>> {
-    if self.in_npm_package(referrer) {
-      // we're in an npm package, so use node resolution
-      Some(self.resolve(specifier, referrer, mode))
-    } else {
-      None
+  ) -> Result<Option<NodeResolution>, AnyError> {
+    let resolution_result = self.resolve(specifier, referrer, mode);
+    match resolution_result {
+      Ok(res) => Ok(Some(res)),
+      Err(err) => {
+        let err = err.into_kind();
+        match err {
+          NodeResolveErrorKind::RelativeJoin(_)
+          | NodeResolveErrorKind::PackageImportsResolve(_)
+          | NodeResolveErrorKind::UnsupportedEsmUrlScheme(_)
+          | NodeResolveErrorKind::DataUrlReferrer(_)
+          | NodeResolveErrorKind::TypesNotFound(_)
+          | NodeResolveErrorKind::FinalizeResolution(_)
+          | NodeResolveErrorKind::UrlToNodeResolution(_) => Err(err.into()),
+          NodeResolveErrorKind::PackageResolve(err) => {
+            let err = err.into_kind();
+            match err {
+              PackageResolveErrorKind::ClosestPkgJson(_)
+              | PackageResolveErrorKind::InvalidModuleSpecifier(_)
+              | PackageResolveErrorKind::ExportsResolve(_)
+              | PackageResolveErrorKind::SubpathResolve(_) => Err(err.into()),
+              PackageResolveErrorKind::PackageFolderResolve(err) => {
+                match err.as_kind() {
+                  PackageFolderResolveErrorKind::Io(
+                    PackageFolderResolveIoError { package_name, .. },
+                  )
+                  | PackageFolderResolveErrorKind::PackageNotFound(
+                    PackageNotFoundError { package_name, .. },
+                  ) => {
+                    if self.in_npm_package(referrer) {
+                      return Err(err.into());
+                    }
+                    if let Some(byonm_npm_resolver) =
+                      self.npm_resolver.as_byonm()
+                    {
+                      if byonm_npm_resolver
+                        .find_ancestor_package_json_with_dep(
+                          package_name,
+                          referrer,
+                        )
+                        .is_some()
+                      {
+                        return Err(anyhow!(
+                        concat!(
+                        "Could not resolve \"{}\", but found it in a package.json. ",
+                        "Deno expects the node_modules/ directory to be up to date. ",
+                        "Did you forget to run `npm install`?"
+                      ),
+                        specifier
+                      ));
+                      }
+                    }
+                    Ok(None)
+                  }
+                  PackageFolderResolveErrorKind::ReferrerNotFound(_) => {
+                    if self.in_npm_package(referrer) {
+                      return Err(err.into());
+                    }
+                    Ok(None)
+                  }
+                }
+              }
+            }
+          }
+        }
+      }
     }
   }
 
@@ -121,18 +182,18 @@ impl CliNodeResolver {
     specifier: &str,
     referrer: &ModuleSpecifier,
     mode: NodeResolutionMode,
-  ) -> Result<Option<NodeResolution>, NodeResolveError> {
+  ) -> Result<NodeResolution, NodeResolveError> {
     let referrer_kind = if self.cjs_resolutions.contains(referrer) {
       NodeModuleKind::Cjs
     } else {
       NodeModuleKind::Esm
     };
 
-    let maybe_res =
+    let res =
       self
         .node_resolver
         .resolve(specifier, referrer, referrer_kind, mode)?;
-    Ok(self.handle_node_resolution(maybe_res))
+    Ok(self.handle_node_resolution(res))
   }
 
   pub fn resolve_req_reference(
@@ -159,16 +220,15 @@ impl CliNodeResolver {
     let package_folder = self
       .npm_resolver
       .resolve_pkg_folder_from_deno_module_req(req, referrer)?;
-    let maybe_resolution = self
-      .maybe_resolve_package_sub_path_from_deno_module(
-        &package_folder,
-        sub_path,
-        Some(referrer),
-        mode,
-      )?;
-    match maybe_resolution {
-      Some(resolution) => Ok(resolution),
-      None => {
+    let resolution_result = self.resolve_package_sub_path_from_deno_module(
+      &package_folder,
+      sub_path,
+      Some(referrer),
+      mode,
+    );
+    match resolution_result {
+      Ok(resolution) => Ok(resolution),
+      Err(err) => {
         if self.npm_resolver.as_byonm().is_some() {
           let package_json_path = package_folder.join("package.json");
           if !self.fs.exists_sync(&package_json_path) {
@@ -178,12 +238,7 @@ impl CliNodeResolver {
             ));
           }
         }
-        Err(anyhow!(
-          "Failed resolving '{}{}' in '{}'.",
-          req,
-          sub_path.map(|s| format!("/{}", s)).unwrap_or_default(),
-          package_folder.display()
-        ))
+        Err(err)
       }
     }
   }
@@ -195,32 +250,7 @@ impl CliNodeResolver {
     maybe_referrer: Option<&ModuleSpecifier>,
     mode: NodeResolutionMode,
   ) -> Result<NodeResolution, AnyError> {
-    self
-      .maybe_resolve_package_sub_path_from_deno_module(
-        package_folder,
-        sub_path,
-        maybe_referrer,
-        mode,
-      )?
-      .ok_or_else(|| {
-        anyhow!(
-          "Failed resolving '{}' in '{}'.",
-          sub_path
-            .map(|s| format!("/{}", s))
-            .unwrap_or_else(|| ".".to_string()),
-          package_folder.display(),
-        )
-      })
-  }
-
-  pub fn maybe_resolve_package_sub_path_from_deno_module(
-    &self,
-    package_folder: &Path,
-    sub_path: Option<&str>,
-    maybe_referrer: Option<&ModuleSpecifier>,
-    mode: NodeResolutionMode,
-  ) -> Result<Option<NodeResolution>, ResolvePkgSubpathFromDenoModuleError> {
-    let maybe_res = self
+    let res = self
       .node_resolver
       .resolve_package_subpath_from_deno_module(
         package_folder,
@@ -228,7 +258,7 @@ impl CliNodeResolver {
         maybe_referrer,
         mode,
       )?;
-    Ok(self.handle_node_resolution(maybe_res))
+    Ok(self.handle_node_resolution(res))
   }
 
   pub fn handle_if_in_node_modules(
@@ -267,13 +297,13 @@ impl CliNodeResolver {
 
   fn handle_node_resolution(
     &self,
-    maybe_resolution: Option<NodeResolution>,
-  ) -> Option<NodeResolution> {
-    if let Some(NodeResolution::CommonJs(specifier)) = &maybe_resolution {
+    resolution: NodeResolution,
+  ) -> NodeResolution {
+    if let NodeResolution::CommonJs(specifier) = &resolution {
       // remember that this was a common js resolution
       self.cjs_resolutions.insert(specifier.clone());
     }
-    maybe_resolution
+    resolution
   }
 }
 
@@ -458,39 +488,6 @@ impl CliGraphResolver {
       bare_node_builtins_enabled: self.bare_node_builtins_enabled,
     }
   }
-
-  // todo(dsherret): update this and the surrounding code to handle the structured errors from NodeResolver
-  fn check_surface_byonm_node_error(
-    &self,
-    specifier: &str,
-    referrer: &ModuleSpecifier,
-    original_err: AnyError,
-    resolver: &ByonmCliNpmResolver,
-  ) -> Result<(), AnyError> {
-    if let Ok((pkg_name, _, _)) = parse_npm_pkg_name(specifier, referrer) {
-      match resolver.resolve_package_folder_from_package(&pkg_name, referrer) {
-        Ok(_) => {
-          return Err(original_err);
-        }
-        Err(_) => {
-          if resolver
-            .find_ancestor_package_json_with_dep(&pkg_name, referrer)
-            .is_some()
-          {
-            return Err(anyhow!(
-              concat!(
-                "Could not resolve \"{}\", but found it in a package.json. ",
-                "Deno expects the node_modules/ directory to be up to date. ",
-                "Did you forget to run `npm install`?"
-              ),
-              specifier
-            ));
-          }
-        }
-      }
-    }
-    Ok(())
-  }
 }
 
 impl Resolver for CliGraphResolver {
@@ -523,6 +520,18 @@ impl Resolver for CliGraphResolver {
     }
 
     let referrer = &referrer_range.specifier;
+
+    // Use node resolution if we're in an npm package
+    if let Some(node_resolver) = self.node_resolver.as_ref() {
+      if referrer.scheme() == "file" && node_resolver.in_npm_package(referrer) {
+        return node_resolver
+          .resolve(specifier, referrer, to_node_mode(mode))
+          .map(|res| res.into_url())
+          .map_err(|e| ResolveError::Other(e.into()));
+      }
+    }
+
+    // Attempt to resolve with the workspace resolver
     let result: Result<_, ResolveError> = self
       .workspace_resolver
       .resolve(specifier, referrer)
@@ -535,7 +544,19 @@ impl Resolver for CliGraphResolver {
     let result = match result {
       Ok(resolution) => match resolution {
         MappedResolution::Normal(specifier)
-        | MappedResolution::ImportMap(specifier) => Ok(specifier),
+        | MappedResolution::ImportMap(specifier) => {
+          // do sloppy imports resolution if enabled
+          if let Some(sloppy_imports_resolver) = &self.sloppy_imports_resolver {
+            Ok(sloppy_imports_resolve(
+              sloppy_imports_resolver,
+              specifier,
+              referrer_range,
+              mode,
+            ))
+          } else {
+            Ok(specifier)
+          }
+        }
         MappedResolution::WorkspaceNpmPackage {
           target_pkg_json: pkg_json,
           sub_path,
@@ -552,8 +573,6 @@ impl Resolver for CliGraphResolver {
           )
           .map_err(ResolveError::Other)
           .map(|res| res.into_url()),
-        // todo(dsherret): for byonm it should do resolution solely based on
-        // the referrer and not the package.json
         MappedResolution::PackageJson {
           dep_result,
           alias,
@@ -604,127 +623,75 @@ impl Resolver for CliGraphResolver {
       Err(err) => Err(err),
     };
 
-    // check if it's an npm specifier that resolves to a workspace member
-    if let Some(node_resolver) = &self.node_resolver {
+    // When the user is vendoring, don't allow them to import directly from the vendor/ directory
+    // as it might cause them confusion or duplicate dependencies. Additionally, this folder has
+    // special treatment in the language server so it will definitely cause issues/confusion there
+    // if they do this.
+    if let Some(vendor_specifier) = &self.maybe_vendor_specifier {
       if let Ok(specifier) = &result {
-        if let Ok(req_ref) = NpmPackageReqReference::from_specifier(specifier) {
+        if specifier.as_str().starts_with(vendor_specifier.as_str()) {
+          return Err(ResolveError::Other(anyhow!("Importing from the vendor directory is not permitted. Use a remote specifier instead or disable vendoring.")));
+        }
+      }
+    }
+
+    let Some(node_resolver) = &self.node_resolver else {
+      return result;
+    };
+
+    let is_byonm = self
+      .npm_resolver
+      .as_ref()
+      .is_some_and(|r| r.as_byonm().is_some());
+    match result {
+      Ok(specifier) => {
+        if let Ok(npm_req_ref) =
+          NpmPackageReqReference::from_specifier(&specifier)
+        {
+          // check if the npm specifier resolves to a workspace member
           if let Some(pkg_folder) = self
             .workspace_resolver
-            .resolve_workspace_pkg_json_folder_for_npm_specifier(req_ref.req())
+            .resolve_workspace_pkg_json_folder_for_npm_specifier(
+              npm_req_ref.req(),
+            )
           {
             return Ok(
               node_resolver
                 .resolve_package_sub_path_from_deno_module(
                   pkg_folder,
-                  req_ref.sub_path(),
+                  npm_req_ref.sub_path(),
                   Some(referrer),
                   to_node_mode(mode),
                 )?
                 .into_url(),
             );
           }
-        }
-      }
-    }
-
-    // do sloppy imports resolution if enabled
-    let result =
-      if let Some(sloppy_imports_resolver) = &self.sloppy_imports_resolver {
-        result.map(|specifier| {
-          sloppy_imports_resolve(
-            sloppy_imports_resolver,
-            specifier,
-            referrer_range,
-            mode,
-          )
-        })
-      } else {
-        result
-      };
-
-    // When the user is vendoring, don't allow them to import directly from the vendor/ directory
-    // as it might cause them confusion or duplicate dependencies. Additionally, this folder has
-    // special treatment in the language server so it will definitely cause issues/confusion there
-    // if they do this.
-    if let Some(vendor_specifier) = &self.maybe_vendor_specifier {
-      if let Ok(specifier) = &result {
-        if specifier.as_str().starts_with(vendor_specifier.as_str()) {
-          return Err(ResolveError::Other(anyhow!("Importing from the vendor directory is not permitted. Use a remote specifier instead or disable vendoring.")));
-        }
-      }
-    }
 
-    if let Some(resolver) =
-      self.npm_resolver.as_ref().and_then(|r| r.as_byonm())
-    {
-      match &result {
-        Ok(specifier) => {
-          if let Ok(npm_req_ref) =
-            NpmPackageReqReference::from_specifier(specifier)
-          {
-            let node_resolver = self.node_resolver.as_ref().unwrap();
+          // do npm resolution for byonm
+          if is_byonm {
             return node_resolver
               .resolve_req_reference(&npm_req_ref, referrer, to_node_mode(mode))
               .map(|res| res.into_url())
               .map_err(|err| err.into());
           }
         }
-        Err(_) => {
-          if referrer.scheme() == "file" {
-            if let Some(node_resolver) = &self.node_resolver {
-              let node_result =
-                node_resolver.resolve(specifier, referrer, to_node_mode(mode));
-              match node_result {
-                Ok(Some(res)) => {
-                  return Ok(res.into_url());
-                }
-                Ok(None) => {
-                  self
-                    .check_surface_byonm_node_error(
-                      specifier,
-                      referrer,
-                      anyhow!("Cannot find \"{}\"", specifier),
-                      resolver,
-                    )
-                    .map_err(ResolveError::Other)?;
-                }
-                Err(err) => {
-                  self
-                    .check_surface_byonm_node_error(
-                      specifier,
-                      referrer,
-                      err.into(),
-                      resolver,
-                    )
-                    .map_err(ResolveError::Other)?;
-                }
-              }
-            }
+
+        Ok(node_resolver.handle_if_in_node_modules(specifier)?)
+      }
+      Err(err) => {
+        // If byonm, check if the bare specifier resolves to an npm package
+        if is_byonm && referrer.scheme() == "file" {
+          let maybe_resolution = node_resolver
+            .resolve_if_for_npm_pkg(specifier, referrer, to_node_mode(mode))
+            .map_err(ResolveError::Other)?;
+          if let Some(res) = maybe_resolution {
+            return Ok(res.into_url());
           }
         }
-      }
-    }
 
-    if referrer.scheme() == "file" {
-      if let Some(node_resolver) = &self.node_resolver {
-        let node_result = node_resolver.resolve_if_in_npm_package(
-          specifier,
-          referrer,
-          to_node_mode(mode),
-        );
-        if let Some(Ok(Some(res))) = node_result {
-          return Ok(res.into_url());
-        }
+        Err(err)
       }
     }
-
-    let specifier = result?;
-    match &self.node_resolver {
-      Some(node_resolver) => node_resolver
-        .handle_if_in_node_modules(specifier)
-        .map_err(|e| e.into()),
-      None => Ok(specifier),
-    }
   }
 }
 
diff --git a/cli/standalone/mod.rs b/cli/standalone/mod.rs
index 74586c1be..561c99c98 100644
--- a/cli/standalone/mod.rs
+++ b/cli/standalone/mod.rs
@@ -151,15 +151,14 @@ impl ModuleLoader for EmbeddedModuleLoader {
       })?
     };
 
-    if let Some(result) = self.shared.node_resolver.resolve_if_in_npm_package(
-      specifier,
-      &referrer,
-      NodeResolutionMode::Execution,
-    ) {
-      return match result? {
-        Some(res) => Ok(res.into_url()),
-        None => Err(generic_error("not found")),
-      };
+    if self.shared.node_resolver.in_npm_package(&referrer) {
+      return Ok(
+        self
+          .shared
+          .node_resolver
+          .resolve(specifier, &referrer, NodeResolutionMode::Execution)?
+          .into_url(),
+      );
     }
 
     let mapped_resolution =
@@ -250,14 +249,12 @@ impl ModuleLoader for EmbeddedModuleLoader {
       Err(err)
         if err.is_unmapped_bare_specifier() && referrer.scheme() == "file" =>
       {
-        // todo(dsherret): return a better error from node resolution so that
-        // we can more easily tell whether to surface it or not
-        let node_result = self.shared.node_resolver.resolve(
+        let maybe_res = self.shared.node_resolver.resolve_if_for_npm_pkg(
           specifier,
           &referrer,
           NodeResolutionMode::Execution,
-        );
-        if let Ok(Some(res)) = node_result {
+        )?;
+        if let Some(res) = maybe_res {
           return Ok(res.into_url());
         }
         Err(err.into())
diff --git a/cli/tsc/mod.rs b/cli/tsc/mod.rs
index f6440266e..424b5c3d3 100644
--- a/cli/tsc/mod.rs
+++ b/cli/tsc/mod.rs
@@ -30,6 +30,8 @@ use deno_graph::GraphKind;
 use deno_graph::Module;
 use deno_graph::ModuleGraph;
 use deno_graph::ResolutionResolved;
+use deno_runtime::deno_node::errors::NodeJsErrorCode;
+use deno_runtime::deno_node::errors::NodeJsErrorCoded;
 use deno_runtime::deno_node::NodeModuleKind;
 use deno_runtime::deno_node::NodeResolution;
 use deno_runtime::deno_node::NodeResolutionMode;
@@ -756,13 +758,21 @@ fn resolve_graph_specifier_types(
           .as_managed()
           .unwrap() // should never be byonm because it won't create Module::Npm
           .resolve_pkg_folder_from_deno_module(module.nv_reference.nv())?;
-        let maybe_resolution =
+        let res_result =
           npm.node_resolver.resolve_package_subpath_from_deno_module(
             &package_folder,
             module.nv_reference.sub_path(),
             Some(referrer),
             NodeResolutionMode::Types,
-          )?;
+          );
+        let maybe_resolution = match res_result {
+          Ok(res) => Some(res),
+          Err(err) => match err.code() {
+            NodeJsErrorCode::ERR_TYPES_NOT_FOUND
+            | NodeJsErrorCode::ERR_MODULE_NOT_FOUND => None,
+            _ => return Err(err.into()),
+          },
+        };
         Ok(Some(NodeResolution::into_specifier_and_media_type(
           maybe_resolution,
         )))
@@ -805,8 +815,7 @@ fn resolve_non_graph_specifier_types(
           referrer_kind,
           NodeResolutionMode::Types,
         )
-        .ok()
-        .flatten(),
+        .ok(),
     )))
   } else if let Ok(npm_req_ref) = NpmPackageReqReference::from_str(specifier) {
     debug_assert_eq!(referrer_kind, NodeModuleKind::Esm);
@@ -817,13 +826,20 @@ fn resolve_non_graph_specifier_types(
     let package_folder = npm
       .npm_resolver
       .resolve_pkg_folder_from_deno_module_req(npm_req_ref.req(), referrer)?;
-    let maybe_resolution = node_resolver
-      .resolve_package_subpath_from_deno_module(
-        &package_folder,
-        npm_req_ref.sub_path(),
-        Some(referrer),
-        NodeResolutionMode::Types,
-      )?;
+    let res_result = node_resolver.resolve_package_subpath_from_deno_module(
+      &package_folder,
+      npm_req_ref.sub_path(),
+      Some(referrer),
+      NodeResolutionMode::Types,
+    );
+    let maybe_resolution = match res_result {
+      Ok(res) => Some(res),
+      Err(err) => match err.code() {
+        NodeJsErrorCode::ERR_TYPES_NOT_FOUND
+        | NodeJsErrorCode::ERR_MODULE_NOT_FOUND => None,
+        _ => return Err(err.into()),
+      },
+    };
     Ok(Some(NodeResolution::into_specifier_and_media_type(
       maybe_resolution,
     )))
diff --git a/cli/worker.rs b/cli/worker.rs
index a639dae41..0d7e61c50 100644
--- a/cli/worker.rs
+++ b/cli/worker.rs
@@ -687,7 +687,7 @@ impl CliMainWorkerFactory {
       return Ok(None);
     }
 
-    let Some(resolution) = self
+    let resolution = self
       .shared
       .node_resolver
       .resolve_package_subpath_from_deno_module(
@@ -695,10 +695,7 @@ impl CliMainWorkerFactory {
         sub_path,
         /* referrer */ None,
         NodeResolutionMode::Execution,
-      )?
-    else {
-      return Ok(None);
-    };
+      )?;
     match &resolution {
       NodeResolution::BuiltIn(_) => Ok(None),
       NodeResolution::CommonJs(specifier) | NodeResolution::Esm(specifier) => {
diff --git a/ext/node/errors.rs b/ext/node/errors.rs
index 11bb011f8..64625d32f 100644
--- a/ext/node/errors.rs
+++ b/ext/node/errors.rs
@@ -49,6 +49,8 @@ pub enum NodeJsErrorCode {
   ERR_UNKNOWN_FILE_EXTENSION,
   ERR_UNSUPPORTED_DIR_IMPORT,
   ERR_UNSUPPORTED_ESM_URL_SCHEME,
+  /// Deno specific since Node doesn't support TypeScript.
+  ERR_TYPES_NOT_FOUND,
 }
 
 impl std::fmt::Display for NodeJsErrorCode {
@@ -70,6 +72,7 @@ impl NodeJsErrorCode {
       ERR_UNKNOWN_FILE_EXTENSION => "ERR_UNKNOWN_FILE_EXTENSION",
       ERR_UNSUPPORTED_DIR_IMPORT => "ERR_UNSUPPORTED_DIR_IMPORT",
       ERR_UNSUPPORTED_ESM_URL_SCHEME => "ERR_UNSUPPORTED_ESM_URL_SCHEME",
+      ERR_TYPES_NOT_FOUND => "ERR_TYPES_NOT_FOUND",
     }
   }
 }
@@ -122,65 +125,98 @@ impl NodeJsErrorCoded for InvalidModuleSpecifierError {
   }
 }
 
+kinded_err!(LegacyResolveError, LegacyResolveErrorKind);
+
 #[derive(Debug, Error)]
-pub enum LegacyMainResolveError {
+pub enum LegacyResolveErrorKind {
+  #[error(transparent)]
+  TypesNotFound(#[from] TypesNotFoundError),
   #[error(transparent)]
-  PathToDeclarationUrl(PathToDeclarationUrlError),
+  ModuleNotFound(#[from] ModuleNotFoundError),
 }
 
-impl NodeJsErrorCoded for LegacyMainResolveError {
+impl NodeJsErrorCoded for LegacyResolveError {
   fn code(&self) -> NodeJsErrorCode {
-    match self {
-      Self::PathToDeclarationUrl(e) => e.code(),
+    match self.as_kind() {
+      LegacyResolveErrorKind::TypesNotFound(e) => e.code(),
+      LegacyResolveErrorKind::ModuleNotFound(e) => e.code(),
     }
   }
 }
 
 kinded_err!(PackageFolderResolveError, PackageFolderResolveErrorKind);
 
+#[derive(Debug, Error)]
+#[error(
+  "Could not find package '{}' from referrer '{}'{}.",
+  package_name,
+  referrer,
+  referrer_extra.as_ref().map(|r| format!(" ({})", r)).unwrap_or_default()
+)]
+pub struct PackageNotFoundError {
+  pub package_name: String,
+  pub referrer: ModuleSpecifier,
+  /// Extra information about the referrer.
+  pub referrer_extra: Option<String>,
+}
+
+impl NodeJsErrorCoded for PackageNotFoundError {
+  fn code(&self) -> NodeJsErrorCode {
+    NodeJsErrorCode::ERR_MODULE_NOT_FOUND
+  }
+}
+
+#[derive(Debug, Error)]
+#[error(
+  "Could not find referrer npm package '{}'{}.",
+  referrer,
+  referrer_extra.as_ref().map(|r| format!(" ({})", r)).unwrap_or_default()
+)]
+pub struct ReferrerNotFoundError {
+  pub referrer: ModuleSpecifier,
+  /// Extra information about the referrer.
+  pub referrer_extra: Option<String>,
+}
+
+impl NodeJsErrorCoded for ReferrerNotFoundError {
+  fn code(&self) -> NodeJsErrorCode {
+    NodeJsErrorCode::ERR_MODULE_NOT_FOUND
+  }
+}
+
+#[derive(Debug, Error)]
+#[error("Failed resolving '{package_name}' from referrer '{referrer}'.")]
+pub struct PackageFolderResolveIoError {
+  pub package_name: String,
+  pub referrer: ModuleSpecifier,
+  #[source]
+  pub source: std::io::Error,
+}
+
+impl NodeJsErrorCoded for PackageFolderResolveIoError {
+  fn code(&self) -> NodeJsErrorCode {
+    NodeJsErrorCode::ERR_MODULE_NOT_FOUND
+  }
+}
+
 impl NodeJsErrorCoded for PackageFolderResolveError {
   fn code(&self) -> NodeJsErrorCode {
     match self.as_kind() {
-      PackageFolderResolveErrorKind::NotFoundPackage { .. }
-      | PackageFolderResolveErrorKind::NotFoundReferrer { .. }
-      | PackageFolderResolveErrorKind::Io { .. } => {
-        NodeJsErrorCode::ERR_MODULE_NOT_FOUND
-      }
+      PackageFolderResolveErrorKind::PackageNotFound(e) => e.code(),
+      PackageFolderResolveErrorKind::ReferrerNotFound(e) => e.code(),
+      PackageFolderResolveErrorKind::Io(e) => e.code(),
     }
   }
 }
 
 #[derive(Debug, Error)]
 pub enum PackageFolderResolveErrorKind {
-  #[error(
-    "Could not find package '{}' from referrer '{}'{}.",
-    package_name,
-    referrer,
-    referrer_extra.as_ref().map(|r| format!(" ({})", r)).unwrap_or_default()
-  )]
-  NotFoundPackage {
-    package_name: String,
-    referrer: ModuleSpecifier,
-    /// Extra information about the referrer.
-    referrer_extra: Option<String>,
-  },
-  #[error(
-    "Could not find referrer npm package '{}'{}.",
-    referrer,
-    referrer_extra.as_ref().map(|r| format!(" ({})", r)).unwrap_or_default()
-  )]
-  NotFoundReferrer {
-    referrer: ModuleSpecifier,
-    /// Extra information about the referrer.
-    referrer_extra: Option<String>,
-  },
-  #[error("Failed resolving '{package_name}' from referrer '{referrer}'.")]
-  Io {
-    package_name: String,
-    referrer: ModuleSpecifier,
-    #[source]
-    source: std::io::Error,
-  },
+  #[error(transparent)]
+  PackageNotFound(#[from] PackageNotFoundError),
+  #[error(transparent)]
+  ReferrerNotFound(#[from] ReferrerNotFoundError),
+  #[error(transparent)]
+  Io(#[from] PackageFolderResolveIoError),
 }
 
 kinded_err!(PackageSubpathResolveError, PackageSubpathResolveErrorKind);
@@ -189,10 +225,8 @@ impl NodeJsErrorCoded for PackageSubpathResolveError {
   fn code(&self) -> NodeJsErrorCode {
     match self.as_kind() {
       PackageSubpathResolveErrorKind::PkgJsonLoad(e) => e.code(),
-      PackageSubpathResolveErrorKind::PackageFolderResolve(e) => e.code(),
       PackageSubpathResolveErrorKind::Exports(e) => e.code(),
-      PackageSubpathResolveErrorKind::LegacyMain(e) => e.code(),
-      PackageSubpathResolveErrorKind::LegacyExact(e) => e.code(),
+      PackageSubpathResolveErrorKind::LegacyResolve(e) => e.code(),
     }
   }
 }
@@ -202,13 +236,9 @@ pub enum PackageSubpathResolveErrorKind {
   #[error(transparent)]
   PkgJsonLoad(#[from] PackageJsonLoadError),
   #[error(transparent)]
-  PackageFolderResolve(#[from] PackageFolderResolveError),
-  #[error(transparent)]
   Exports(PackageExportsResolveError),
   #[error(transparent)]
-  LegacyMain(LegacyMainResolveError),
-  #[error(transparent)]
-  LegacyExact(PathToDeclarationUrlError),
+  LegacyResolve(LegacyResolveError),
 }
 
 #[derive(Debug, Error)]
@@ -254,7 +284,7 @@ impl NodeJsErrorCoded for PackageTargetResolveError {
       PackageTargetResolveErrorKind::InvalidPackageTarget(e) => e.code(),
       PackageTargetResolveErrorKind::InvalidModuleSpecifier(e) => e.code(),
       PackageTargetResolveErrorKind::PackageResolve(e) => e.code(),
-      PackageTargetResolveErrorKind::PathToDeclarationUrl(e) => e.code(),
+      PackageTargetResolveErrorKind::TypesNotFound(e) => e.code(),
     }
   }
 }
@@ -270,7 +300,7 @@ pub enum PackageTargetResolveErrorKind {
   #[error(transparent)]
   PackageResolve(#[from] PackageResolveError),
   #[error(transparent)]
-  PathToDeclarationUrl(#[from] PathToDeclarationUrlError),
+  TypesNotFound(#[from] TypesNotFoundError),
 }
 
 kinded_err!(PackageExportsResolveError, PackageExportsResolveErrorKind);
@@ -293,16 +323,23 @@ pub enum PackageExportsResolveErrorKind {
 }
 
 #[derive(Debug, Error)]
-pub enum PathToDeclarationUrlError {
-  #[error(transparent)]
-  SubPath(#[from] PackageSubpathResolveError),
+#[error(
+    "[{}] Could not find types for '{}'{}",
+    self.code(),
+    self.0.code_specifier,
+    self.0.maybe_referrer.as_ref().map(|r| format!(" imported from '{}'", r)).unwrap_or_default(),
+  )]
+pub struct TypesNotFoundError(pub Box<TypesNotFoundErrorData>);
+
+#[derive(Debug)]
+pub struct TypesNotFoundErrorData {
+  pub code_specifier: ModuleSpecifier,
+  pub maybe_referrer: Option<ModuleSpecifier>,
 }
 
-impl NodeJsErrorCoded for PathToDeclarationUrlError {
+impl NodeJsErrorCoded for TypesNotFoundError {
   fn code(&self) -> NodeJsErrorCode {
-    match self {
-      PathToDeclarationUrlError::SubPath(e) => e.code(),
-    }
+    NodeJsErrorCode::ERR_TYPES_NOT_FOUND
   }
 }
 
@@ -441,6 +478,7 @@ impl NodeJsErrorCoded for PackageResolveError {
     match self.as_kind() {
       PackageResolveErrorKind::ClosestPkgJson(e) => e.code(),
       PackageResolveErrorKind::InvalidModuleSpecifier(e) => e.code(),
+      PackageResolveErrorKind::PackageFolderResolve(e) => e.code(),
       PackageResolveErrorKind::ExportsResolve(e) => e.code(),
       PackageResolveErrorKind::SubpathResolve(e) => e.code(),
     }
@@ -454,37 +492,49 @@ pub enum PackageResolveErrorKind {
   #[error(transparent)]
   InvalidModuleSpecifier(#[from] InvalidModuleSpecifierError),
   #[error(transparent)]
+  PackageFolderResolve(#[from] PackageFolderResolveError),
+  #[error(transparent)]
   ExportsResolve(#[from] PackageExportsResolveError),
   #[error(transparent)]
   SubpathResolve(#[from] PackageSubpathResolveError),
 }
 
 #[derive(Debug, Error)]
-pub enum NodeResolveError {
-  #[error("Failed joining '{path}' from '{base}'.")]
-  RelativeJoinError {
-    path: String,
-    base: ModuleSpecifier,
-    #[source]
-    source: url::ParseError,
-  },
+#[error("Failed joining '{path}' from '{base}'.")]
+pub struct NodeResolveRelativeJoinError {
+  pub path: String,
+  pub base: ModuleSpecifier,
+  #[source]
+  pub source: url::ParseError,
+}
+
+#[derive(Debug, Error)]
+#[error("Failed resolving specifier from data url referrer.")]
+pub struct DataUrlReferrerError {
+  #[source]
+  pub source: url::ParseError,
+}
+
+kinded_err!(NodeResolveError, NodeResolveErrorKind);
+
+#[derive(Debug, Error)]
+pub enum NodeResolveErrorKind {
+  #[error(transparent)]
+  RelativeJoin(#[from] NodeResolveRelativeJoinError),
   #[error(transparent)]
   PackageImportsResolve(#[from] PackageImportsResolveError),
   #[error(transparent)]
   UnsupportedEsmUrlScheme(#[from] UnsupportedEsmUrlSchemeError),
-  #[error("Failed resolving specifier from data url referrer.")]
-  DataUrlReferrerFailed {
-    #[source]
-    source: url::ParseError,
-  },
+  #[error(transparent)]
+  DataUrlReferrer(#[from] DataUrlReferrerError),
   #[error(transparent)]
   PackageResolve(#[from] PackageResolveError),
   #[error(transparent)]
-  PathToDeclarationUrl(#[from] PathToDeclarationUrlError),
-  #[error(transparent)]
-  UrlToNodeResolution(#[from] UrlToNodeResolutionError),
+  TypesNotFound(#[from] TypesNotFoundError),
   #[error(transparent)]
   FinalizeResolution(#[from] FinalizeResolutionError),
+  #[error(transparent)]
+  UrlToNodeResolution(#[from] UrlToNodeResolutionError),
 }
 
 kinded_err!(FinalizeResolutionError, FinalizeResolutionErrorKind);
@@ -499,6 +549,16 @@ pub enum FinalizeResolutionErrorKind {
   UnsupportedDirImport(#[from] UnsupportedDirImportError),
 }
 
+impl NodeJsErrorCoded for FinalizeResolutionError {
+  fn code(&self) -> NodeJsErrorCode {
+    match self.as_kind() {
+      FinalizeResolutionErrorKind::InvalidModuleSpecifierError(e) => e.code(),
+      FinalizeResolutionErrorKind::ModuleNotFound(e) => e.code(),
+      FinalizeResolutionErrorKind::UnsupportedDirImport(e) => e.code(),
+    }
+  }
+}
+
 #[derive(Debug, Error)]
 #[error(
   "[{}] Cannot find {} '{}'{}",
@@ -513,9 +573,9 @@ pub struct ModuleNotFoundError {
   pub typ: &'static str,
 }
 
-impl ModuleNotFoundError {
-  pub fn code(&self) -> &'static str {
-    "ERR_MODULE_NOT_FOUND"
+impl NodeJsErrorCoded for ModuleNotFoundError {
+  fn code(&self) -> NodeJsErrorCode {
+    NodeJsErrorCode::ERR_MODULE_NOT_FOUND
   }
 }
 
diff --git a/ext/node/lib.rs b/ext/node/lib.rs
index 6f7185148..21af5a094 100644
--- a/ext/node/lib.rs
+++ b/ext/node/lib.rs
@@ -46,7 +46,6 @@ pub use path::PathClean;
 pub use polyfill::is_builtin_node_module;
 pub use polyfill::SUPPORTED_BUILTIN_NODE_MODULES;
 pub use polyfill::SUPPORTED_BUILTIN_NODE_MODULES_WITH_PREFIX;
-pub use resolution::parse_npm_pkg_name;
 pub use resolution::NodeModuleKind;
 pub use resolution::NodeResolution;
 pub use resolution::NodeResolutionMode;
diff --git a/ext/node/resolution.rs b/ext/node/resolution.rs
index 476b4f59c..6417835a2 100644
--- a/ext/node/resolution.rs
+++ b/ext/node/resolution.rs
@@ -18,14 +18,16 @@ use deno_package_json::PackageJsonRc;
 use crate::errors;
 use crate::errors::CanonicalizingPkgJsonDirError;
 use crate::errors::ClosestPkgJsonError;
+use crate::errors::DataUrlReferrerError;
 use crate::errors::FinalizeResolutionError;
 use crate::errors::InvalidModuleSpecifierError;
 use crate::errors::InvalidPackageTargetError;
-use crate::errors::LegacyMainResolveError;
+use crate::errors::LegacyResolveError;
 use crate::errors::ModuleNotFoundError;
 use crate::errors::NodeJsErrorCode;
 use crate::errors::NodeJsErrorCoded;
 use crate::errors::NodeResolveError;
+use crate::errors::NodeResolveRelativeJoinError;
 use crate::errors::PackageExportsResolveError;
 use crate::errors::PackageImportNotDefinedError;
 use crate::errors::PackageImportsResolveError;
@@ -38,11 +40,12 @@ use crate::errors::PackageSubpathResolveErrorKind;
 use crate::errors::PackageTargetNotFoundError;
 use crate::errors::PackageTargetResolveError;
 use crate::errors::PackageTargetResolveErrorKind;
-use crate::errors::PathToDeclarationUrlError;
 use crate::errors::ResolveBinaryCommandsError;
 use crate::errors::ResolvePkgJsonBinExportError;
 use crate::errors::ResolvePkgSubpathFromDenoModuleError;
 use crate::errors::TypeScriptNotSupportedInNpmError;
+use crate::errors::TypesNotFoundError;
+use crate::errors::TypesNotFoundErrorData;
 use crate::errors::UnsupportedDirImportError;
 use crate::errors::UnsupportedEsmUrlSchemeError;
 use crate::errors::UrlToNodeResolutionError;
@@ -55,6 +58,7 @@ use crate::PathClean;
 
 pub static DEFAULT_CONDITIONS: &[&str] = &["deno", "node", "import"];
 pub static REQUIRE_CONDITIONS: &[&str] = &["require", "node"];
+static TYPES_ONLY_CONDITIONS: &[&str] = &["types"];
 
 pub type NodeModuleKind = deno_package_json::NodeModuleKind;
 
@@ -177,23 +181,23 @@ impl NodeResolver {
     referrer: &ModuleSpecifier,
     referrer_kind: NodeModuleKind,
     mode: NodeResolutionMode,
-  ) -> Result<Option<NodeResolution>, NodeResolveError> {
+  ) -> Result<NodeResolution, NodeResolveError> {
     // Note: if we are here, then the referrer is an esm module
     // TODO(bartlomieju): skipped "policy" part as we don't plan to support it
 
     if crate::is_builtin_node_module(specifier) {
-      return Ok(Some(NodeResolution::BuiltIn(specifier.to_string())));
+      return Ok(NodeResolution::BuiltIn(specifier.to_string()));
     }
 
     if let Ok(url) = Url::parse(specifier) {
       if url.scheme() == "data" {
-        return Ok(Some(NodeResolution::Esm(url)));
+        return Ok(NodeResolution::Esm(url));
       }
 
       if let Some(module_name) =
         get_module_name_from_builtin_node_module_specifier(&url)
       {
-        return Ok(Some(NodeResolution::BuiltIn(module_name.to_string())));
+        return Ok(NodeResolution::BuiltIn(module_name.to_string()));
       }
 
       let protocol = url.scheme();
@@ -209,14 +213,14 @@ impl NodeResolver {
 
       // todo(dsherret): this seems wrong
       if referrer.scheme() == "data" {
-        let url = referrer.join(specifier).map_err(|source| {
-          NodeResolveError::DataUrlReferrerFailed { source }
-        })?;
-        return Ok(Some(NodeResolution::Esm(url)));
+        let url = referrer
+          .join(specifier)
+          .map_err(|source| DataUrlReferrerError { source })?;
+        return Ok(NodeResolution::Esm(url));
       }
     }
 
-    let maybe_url = self.module_resolve(
+    let url = self.module_resolve(
       specifier,
       referrer,
       referrer_kind,
@@ -226,15 +230,19 @@ impl NodeResolver {
       },
       mode,
     )?;
-    let url = match maybe_url {
-      Some(url) => url,
-      None => return Ok(None),
+
+    let url = if mode.is_types() {
+      let file_path = to_file_path(&url);
+      self.path_to_declaration_url(&file_path, Some(referrer), referrer_kind)?
+    } else {
+      url
     };
 
+    let url = self.finalize_resolution(url, Some(referrer))?;
     let resolve_response = self.url_to_node_resolution(url)?;
     // TODO(bartlomieju): skipped checking errors for commonJS resolution and
     // "preserveSymlinksMain"/"preserveSymlinks" options.
-    Ok(Some(resolve_response))
+    Ok(resolve_response)
   }
 
   fn module_resolve(
@@ -244,12 +252,10 @@ impl NodeResolver {
     referrer_kind: NodeModuleKind,
     conditions: &[&str],
     mode: NodeResolutionMode,
-  ) -> Result<Option<ModuleSpecifier>, NodeResolveError> {
-    // note: if we're here, the referrer is an esm module
-    let maybe_url = if should_be_treated_as_relative_or_absolute_path(specifier)
-    {
-      Some(referrer.join(specifier).map_err(|err| {
-        NodeResolveError::RelativeJoinError {
+  ) -> Result<ModuleSpecifier, NodeResolveError> {
+    if should_be_treated_as_relative_or_absolute_path(specifier) {
+      Ok(referrer.join(specifier).map_err(|err| {
+        NodeResolveRelativeJoinError {
           path: specifier.to_string(),
           base: referrer.clone(),
           source: err,
@@ -260,7 +266,7 @@ impl NodeResolver {
         .get_closest_package_json(referrer)
         .map_err(PackageImportsResolveErrorKind::ClosestPkgJson)
         .map_err(|err| PackageImportsResolveError(Box::new(err)))?;
-      Some(self.package_imports_resolve(
+      Ok(self.package_imports_resolve(
         specifier,
         Some(referrer),
         referrer_kind,
@@ -269,32 +275,16 @@ impl NodeResolver {
         mode,
       )?)
     } else if let Ok(resolved) = Url::parse(specifier) {
-      Some(resolved)
+      Ok(resolved)
     } else {
-      self.package_resolve(
+      Ok(self.package_resolve(
         specifier,
         referrer,
         referrer_kind,
         conditions,
         mode,
-      )?
-    };
-
-    let Some(url) = maybe_url else {
-      return Ok(None);
-    };
-
-    let maybe_url = if mode.is_types() {
-      let file_path = to_file_path(&url);
-      self.path_to_declaration_url(&file_path, Some(referrer), referrer_kind)?
-    } else {
-      Some(url)
-    };
-
-    Ok(match maybe_url {
-      Some(url) => Some(self.finalize_resolution(url, Some(referrer))?),
-      None => None,
-    })
+      )?)
+    }
   }
 
   fn finalize_resolution(
@@ -369,12 +359,12 @@ impl NodeResolver {
     package_subpath: Option<&str>,
     maybe_referrer: Option<&ModuleSpecifier>,
     mode: NodeResolutionMode,
-  ) -> Result<Option<NodeResolution>, ResolvePkgSubpathFromDenoModuleError> {
+  ) -> Result<NodeResolution, ResolvePkgSubpathFromDenoModuleError> {
     let node_module_kind = NodeModuleKind::Esm;
     let package_subpath = package_subpath
       .map(|s| format!("./{s}"))
       .unwrap_or_else(|| ".".to_string());
-    let maybe_resolved_url = self.resolve_package_dir_subpath(
+    let resolved_url = self.resolve_package_dir_subpath(
       package_dir,
       &package_subpath,
       maybe_referrer,
@@ -382,14 +372,10 @@ impl NodeResolver {
       DEFAULT_CONDITIONS,
       mode,
     )?;
-    let resolved_url = match maybe_resolved_url {
-      Some(resolved_url) => resolved_url,
-      None => return Ok(None),
-    };
     let resolve_response = self.url_to_node_resolution(resolved_url)?;
     // TODO(bartlomieju): skipped checking errors for commonJS resolution and
     // "preserveSymlinksMain"/"preserveSymlinks" options.
-    Ok(Some(resolve_response))
+    Ok(resolve_response)
   }
 
   pub fn resolve_binary_commands(
@@ -475,7 +461,7 @@ impl NodeResolver {
     path: &Path,
     maybe_referrer: Option<&ModuleSpecifier>,
     referrer_kind: NodeModuleKind,
-  ) -> Result<Option<ModuleSpecifier>, PathToDeclarationUrlError> {
+  ) -> Result<ModuleSpecifier, TypesNotFoundError> {
     fn probe_extensions(
       fs: &dyn deno_fs::FileSystem,
       path: &Path,
@@ -525,15 +511,15 @@ impl NodeResolver {
       || lowercase_path.ends_with(".d.cts")
       || lowercase_path.ends_with(".d.mts")
     {
-      return Ok(Some(to_file_specifier(path)));
+      return Ok(to_file_specifier(path));
     }
     if let Some(path) =
       probe_extensions(&*self.fs, path, &lowercase_path, referrer_kind)
     {
-      return Ok(Some(to_file_specifier(&path)));
+      return Ok(to_file_specifier(&path));
     }
     if self.fs.is_dir_sync(path) {
-      let maybe_resolution = self.resolve_package_dir_subpath(
+      let resolution_result = self.resolve_package_dir_subpath(
         path,
         /* sub path */ ".",
         maybe_referrer,
@@ -543,9 +529,9 @@ impl NodeResolver {
           NodeModuleKind::Cjs => REQUIRE_CONDITIONS,
         },
         NodeResolutionMode::Types,
-      )?;
-      if let Some(resolution) = maybe_resolution {
-        return Ok(Some(resolution));
+      );
+      if let Ok(resolution) = resolution_result {
+        return Ok(resolution);
       }
       let index_path = path.join("index.js");
       if let Some(path) = probe_extensions(
@@ -554,14 +540,17 @@ impl NodeResolver {
         &index_path.to_string_lossy().to_lowercase(),
         referrer_kind,
       ) {
-        return Ok(Some(to_file_specifier(&path)));
+        return Ok(to_file_specifier(&path));
       }
     }
     // allow resolving .css files for types resolution
     if lowercase_path.ends_with(".css") {
-      return Ok(Some(to_file_specifier(path)));
+      return Ok(to_file_specifier(path));
     }
-    Ok(None)
+    Err(TypesNotFoundError(Box::new(TypesNotFoundErrorData {
+      code_specifier: to_file_specifier(path),
+      maybe_referrer: maybe_referrer.cloned(),
+    })))
   }
 
   #[allow(clippy::too_many_arguments)]
@@ -719,22 +708,32 @@ impl NodeResolver {
               conditions,
               mode,
             ) {
-              Ok(Some(url)) => Ok(url),
-              Ok(None) => Err(
-                PackageTargetResolveErrorKind::NotFound(
-                  PackageTargetNotFoundError {
-                    pkg_json_path: package_json_path.to_path_buf(),
-                    target: export_target.to_string(),
-                    maybe_referrer: maybe_referrer.map(ToOwned::to_owned),
-                    referrer_kind,
-                    mode,
-                  },
-                )
-                .into(),
-              ),
-              Err(err) => {
-                Err(PackageTargetResolveErrorKind::PackageResolve(err).into())
-              }
+              Ok(url) => Ok(url),
+              Err(err) => match err.code() {
+                NodeJsErrorCode::ERR_INVALID_MODULE_SPECIFIER
+                | NodeJsErrorCode::ERR_INVALID_PACKAGE_CONFIG
+                | NodeJsErrorCode::ERR_INVALID_PACKAGE_TARGET
+                | NodeJsErrorCode::ERR_PACKAGE_IMPORT_NOT_DEFINED
+                | NodeJsErrorCode::ERR_PACKAGE_PATH_NOT_EXPORTED
+                | NodeJsErrorCode::ERR_UNKNOWN_FILE_EXTENSION
+                | NodeJsErrorCode::ERR_UNSUPPORTED_DIR_IMPORT
+                | NodeJsErrorCode::ERR_UNSUPPORTED_ESM_URL_SCHEME
+                | NodeJsErrorCode::ERR_TYPES_NOT_FOUND => {
+                  Err(PackageTargetResolveErrorKind::PackageResolve(err).into())
+                }
+                NodeJsErrorCode::ERR_MODULE_NOT_FOUND => Err(
+                  PackageTargetResolveErrorKind::NotFound(
+                    PackageTargetNotFoundError {
+                      pkg_json_path: package_json_path.to_path_buf(),
+                      target: export_target.to_string(),
+                      maybe_referrer: maybe_referrer.map(ToOwned::to_owned),
+                      referrer_kind,
+                      mode,
+                    },
+                  )
+                  .into(),
+                ),
+              },
             };
 
             return match result {
@@ -832,6 +831,62 @@ impl NodeResolver {
     conditions: &[&str],
     mode: NodeResolutionMode,
   ) -> Result<Option<ModuleSpecifier>, PackageTargetResolveError> {
+    let result = self.resolve_package_target_inner(
+      package_json_path,
+      target,
+      subpath,
+      package_subpath,
+      maybe_referrer,
+      referrer_kind,
+      pattern,
+      internal,
+      conditions,
+      mode,
+    );
+    match result {
+      Ok(maybe_resolved) => Ok(maybe_resolved),
+      Err(err) => {
+        if mode.is_types()
+          && err.code() == NodeJsErrorCode::ERR_TYPES_NOT_FOUND
+          && conditions != TYPES_ONLY_CONDITIONS
+        {
+          // try resolving with just "types" conditions for when someone misconfigures
+          // and puts the "types" condition in the wrong place
+          if let Ok(Some(resolved)) = self.resolve_package_target_inner(
+            package_json_path,
+            target,
+            subpath,
+            package_subpath,
+            maybe_referrer,
+            referrer_kind,
+            pattern,
+            internal,
+            TYPES_ONLY_CONDITIONS,
+            mode,
+          ) {
+            return Ok(Some(resolved));
+          }
+        }
+
+        Err(err)
+      }
+    }
+  }
+
+  #[allow(clippy::too_many_arguments)]
+  fn resolve_package_target_inner(
+    &self,
+    package_json_path: &Path,
+    target: &Value,
+    subpath: &str,
+    package_subpath: &str,
+    maybe_referrer: Option<&ModuleSpecifier>,
+    referrer_kind: NodeModuleKind,
+    pattern: bool,
+    internal: bool,
+    conditions: &[&str],
+    mode: NodeResolutionMode,
+  ) -> Result<Option<ModuleSpecifier>, PackageTargetResolveError> {
     if let Some(target) = target.as_str() {
       let url = self.resolve_package_target_string(
         target,
@@ -847,11 +902,11 @@ impl NodeResolver {
       )?;
       if mode.is_types() && url.scheme() == "file" {
         let path = url.to_file_path().unwrap();
-        return Ok(self.path_to_declaration_url(
+        return Ok(Some(self.path_to_declaration_url(
           &path,
           maybe_referrer,
           referrer_kind,
-        )?);
+        )?));
       } else {
         return Ok(Some(url));
       }
@@ -1069,41 +1124,37 @@ impl NodeResolver {
     referrer_kind: NodeModuleKind,
     conditions: &[&str],
     mode: NodeResolutionMode,
-  ) -> Result<Option<ModuleSpecifier>, PackageResolveError> {
+  ) -> Result<ModuleSpecifier, PackageResolveError> {
     let (package_name, package_subpath, _is_scoped) =
       parse_npm_pkg_name(specifier, referrer)?;
 
-    let Some(package_config) = self.get_closest_package_json(referrer)? else {
-      return Ok(None);
-    };
-    // ResolveSelf
-    if package_config.name.as_ref() == Some(&package_name) {
-      if let Some(exports) = &package_config.exports {
-        return self
-          .package_exports_resolve(
-            &package_config.path,
-            &package_subpath,
-            exports,
-            Some(referrer),
-            referrer_kind,
-            conditions,
-            mode,
-          )
-          .map(Some)
-          .map_err(|err| err.into());
+    if let Some(package_config) = self.get_closest_package_json(referrer)? {
+      // ResolveSelf
+      if package_config.name.as_ref() == Some(&package_name) {
+        if let Some(exports) = &package_config.exports {
+          return self
+            .package_exports_resolve(
+              &package_config.path,
+              &package_subpath,
+              exports,
+              Some(referrer),
+              referrer_kind,
+              conditions,
+              mode,
+            )
+            .map_err(|err| err.into());
+        }
       }
     }
 
-    self
-      .resolve_package_subpath_for_package(
-        &package_name,
-        &package_subpath,
-        referrer,
-        referrer_kind,
-        conditions,
-        mode,
-      )
-      .map_err(|err| err.into())
+    self.resolve_package_subpath_for_package(
+      &package_name,
+      &package_subpath,
+      referrer,
+      referrer_kind,
+      conditions,
+      mode,
+    )
   }
 
   #[allow(clippy::too_many_arguments)]
@@ -1115,7 +1166,7 @@ impl NodeResolver {
     referrer_kind: NodeModuleKind,
     conditions: &[&str],
     mode: NodeResolutionMode,
-  ) -> Result<Option<ModuleSpecifier>, PackageSubpathResolveError> {
+  ) -> Result<ModuleSpecifier, PackageResolveError> {
     let result = self.resolve_package_subpath_for_package_inner(
       package_name,
       package_subpath,
@@ -1124,10 +1175,10 @@ impl NodeResolver {
       conditions,
       mode,
     );
-    if mode.is_types() && !matches!(result, Ok(Some(_))) {
+    if mode.is_types() && !matches!(result, Ok(ModuleSpecifier { .. })) {
       // try to resolve with the @types package
       let package_name = types_package_name(package_name);
-      if let Ok(Some(result)) = self.resolve_package_subpath_for_package_inner(
+      if let Ok(result) = self.resolve_package_subpath_for_package_inner(
         &package_name,
         package_subpath,
         referrer,
@@ -1135,7 +1186,7 @@ impl NodeResolver {
         conditions,
         mode,
       ) {
-        return Ok(Some(result));
+        return Ok(result);
       }
     }
     result
@@ -1150,7 +1201,7 @@ impl NodeResolver {
     referrer_kind: NodeModuleKind,
     conditions: &[&str],
     mode: NodeResolutionMode,
-  ) -> Result<Option<ModuleSpecifier>, PackageSubpathResolveError> {
+  ) -> Result<ModuleSpecifier, PackageResolveError> {
     let package_dir_path = self
       .npm_resolver
       .resolve_package_folder_from_package(package_name, referrer)?;
@@ -1169,14 +1220,16 @@ impl NodeResolver {
     // ))
 
     // Package match.
-    self.resolve_package_dir_subpath(
-      &package_dir_path,
-      package_subpath,
-      Some(referrer),
-      referrer_kind,
-      conditions,
-      mode,
-    )
+    self
+      .resolve_package_dir_subpath(
+        &package_dir_path,
+        package_subpath,
+        Some(referrer),
+        referrer_kind,
+        conditions,
+        mode,
+      )
+      .map_err(|err| err.into())
   }
 
   #[allow(clippy::too_many_arguments)]
@@ -1188,7 +1241,7 @@ impl NodeResolver {
     referrer_kind: NodeModuleKind,
     conditions: &[&str],
     mode: NodeResolutionMode,
-  ) -> Result<Option<ModuleSpecifier>, PackageSubpathResolveError> {
+  ) -> Result<ModuleSpecifier, PackageSubpathResolveError> {
     let package_json_path = package_dir_path.join("package.json");
     match self.load_package_json(&package_json_path)? {
       Some(pkg_json) => self.resolve_package_subpath(
@@ -1207,7 +1260,9 @@ impl NodeResolver {
           referrer_kind,
           mode,
         )
-        .map_err(|err| PackageSubpathResolveErrorKind::LegacyExact(err).into()),
+        .map_err(|err| {
+          PackageSubpathResolveErrorKind::LegacyResolve(err).into()
+        }),
     }
   }
 
@@ -1220,7 +1275,7 @@ impl NodeResolver {
     referrer_kind: NodeModuleKind,
     conditions: &[&str],
     mode: NodeResolutionMode,
-  ) -> Result<Option<ModuleSpecifier>, PackageSubpathResolveError> {
+  ) -> Result<ModuleSpecifier, PackageSubpathResolveError> {
     if let Some(exports) = &package_json.exports {
       let result = self.package_exports_resolve(
         &package_json.path,
@@ -1232,13 +1287,13 @@ impl NodeResolver {
         mode,
       );
       match result {
-        Ok(found) => return Ok(Some(found)),
+        Ok(found) => return Ok(found),
         Err(exports_err) => {
           if mode.is_types() && package_subpath == "." {
             return self
               .legacy_main_resolve(package_json, referrer, referrer_kind, mode)
               .map_err(|err| {
-                PackageSubpathResolveErrorKind::LegacyMain(err).into()
+                PackageSubpathResolveErrorKind::LegacyResolve(err).into()
               });
           }
           return Err(
@@ -1251,7 +1306,9 @@ impl NodeResolver {
     if package_subpath == "." {
       return self
         .legacy_main_resolve(package_json, referrer, referrer_kind, mode)
-        .map_err(|err| PackageSubpathResolveErrorKind::LegacyMain(err).into());
+        .map_err(|err| {
+          PackageSubpathResolveErrorKind::LegacyResolve(err).into()
+        });
     }
 
     self
@@ -1262,7 +1319,9 @@ impl NodeResolver {
         referrer_kind,
         mode,
       )
-      .map_err(|err| PackageSubpathResolveErrorKind::LegacyExact(err).into())
+      .map_err(|err| {
+        PackageSubpathResolveErrorKind::LegacyResolve(err.into()).into()
+      })
   }
 
   fn resolve_subpath_exact(
@@ -1272,13 +1331,13 @@ impl NodeResolver {
     referrer: Option<&ModuleSpecifier>,
     referrer_kind: NodeModuleKind,
     mode: NodeResolutionMode,
-  ) -> Result<Option<ModuleSpecifier>, PathToDeclarationUrlError> {
+  ) -> Result<ModuleSpecifier, TypesNotFoundError> {
     assert_ne!(package_subpath, ".");
     let file_path = directory.join(package_subpath);
     if mode.is_types() {
       Ok(self.path_to_declaration_url(&file_path, referrer, referrer_kind)?)
     } else {
-      Ok(Some(to_file_specifier(&file_path)))
+      Ok(to_file_specifier(&file_path))
     }
   }
 
@@ -1286,20 +1345,22 @@ impl NodeResolver {
     &self,
     directory: &Path,
     package_subpath: &str,
-    referrer: Option<&ModuleSpecifier>,
+    maybe_referrer: Option<&ModuleSpecifier>,
     referrer_kind: NodeModuleKind,
     mode: NodeResolutionMode,
-  ) -> Result<Option<ModuleSpecifier>, PathToDeclarationUrlError> {
+  ) -> Result<ModuleSpecifier, LegacyResolveError> {
     if package_subpath == "." {
-      Ok(self.legacy_index_resolve(directory, referrer_kind, mode))
+      self.legacy_index_resolve(directory, maybe_referrer, referrer_kind, mode)
     } else {
-      self.resolve_subpath_exact(
-        directory,
-        package_subpath,
-        referrer,
-        referrer_kind,
-        mode,
-      )
+      self
+        .resolve_subpath_exact(
+          directory,
+          package_subpath,
+          maybe_referrer,
+          referrer_kind,
+          mode,
+        )
+        .map_err(|err| err.into())
     }
   }
 
@@ -1348,7 +1409,7 @@ impl NodeResolver {
     maybe_referrer: Option<&ModuleSpecifier>,
     referrer_kind: NodeModuleKind,
     mode: NodeResolutionMode,
-  ) -> Result<Option<ModuleSpecifier>, LegacyMainResolveError> {
+  ) -> Result<ModuleSpecifier, LegacyResolveError> {
     let maybe_main = if mode.is_types() {
       match package_json.types.as_ref() {
         Some(types) => Some(types.as_str()),
@@ -1357,11 +1418,14 @@ impl NodeResolver {
           // a corresponding declaration file
           if let Some(main) = package_json.main(referrer_kind) {
             let main = package_json.path.parent().unwrap().join(main).clean();
-            let maybe_decl_url = self
-              .path_to_declaration_url(&main, maybe_referrer, referrer_kind)
-              .map_err(LegacyMainResolveError::PathToDeclarationUrl)?;
-            if let Some(path) = maybe_decl_url {
-              return Ok(Some(path));
+            let decl_url_result = self.path_to_declaration_url(
+              &main,
+              maybe_referrer,
+              referrer_kind,
+            );
+            // don't surface errors, fallback to checking the index now
+            if let Ok(url) = decl_url_result {
+              return Ok(url);
             }
           }
           None
@@ -1374,7 +1438,7 @@ impl NodeResolver {
     if let Some(main) = maybe_main {
       let guess = package_json.path.parent().unwrap().join(main).clean();
       if self.fs.is_file_sync(&guess) {
-        return Ok(Some(to_file_specifier(&guess)));
+        return Ok(to_file_specifier(&guess));
       }
 
       // todo(dsherret): investigate exactly how node and typescript handles this
@@ -1404,24 +1468,26 @@ impl NodeResolver {
           .clean();
         if self.fs.is_file_sync(&guess) {
           // TODO(bartlomieju): emitLegacyIndexDeprecation()
-          return Ok(Some(to_file_specifier(&guess)));
+          return Ok(to_file_specifier(&guess));
         }
       }
     }
 
-    Ok(self.legacy_index_resolve(
+    self.legacy_index_resolve(
       package_json.path.parent().unwrap(),
+      maybe_referrer,
       referrer_kind,
       mode,
-    ))
+    )
   }
 
   fn legacy_index_resolve(
     &self,
     directory: &Path,
+    maybe_referrer: Option<&ModuleSpecifier>,
     referrer_kind: NodeModuleKind,
     mode: NodeResolutionMode,
-  ) -> Option<ModuleSpecifier> {
+  ) -> Result<ModuleSpecifier, LegacyResolveError> {
     let index_file_names = if mode.is_types() {
       // todo(dsherret): investigate exactly how typescript does this
       match referrer_kind {
@@ -1435,11 +1501,28 @@ impl NodeResolver {
       let guess = directory.join(index_file_name).clean();
       if self.fs.is_file_sync(&guess) {
         // TODO(bartlomieju): emitLegacyIndexDeprecation()
-        return Some(to_file_specifier(&guess));
+        return Ok(to_file_specifier(&guess));
       }
     }
 
-    None
+    if mode.is_types() {
+      Err(
+        TypesNotFoundError(Box::new(TypesNotFoundErrorData {
+          code_specifier: to_file_specifier(&directory.join("index.js")),
+          maybe_referrer: maybe_referrer.cloned(),
+        }))
+        .into(),
+      )
+    } else {
+      Err(
+        ModuleNotFoundError {
+          specifier: to_file_specifier(&directory.join("index.js")),
+          typ: "module",
+          maybe_referrer: maybe_referrer.cloned(),
+        }
+        .into(),
+      )
+    }
   }
 }
 
@@ -1557,7 +1640,7 @@ fn should_be_treated_as_relative_or_absolute_path(specifier: &str) -> bool {
 // TODO(ry) We very likely have this utility function elsewhere in Deno.
 fn is_relative_specifier(specifier: &str) -> bool {
   let specifier_len = specifier.len();
-  let specifier_chars: Vec<_> = specifier.chars().collect();
+  let specifier_chars: Vec<_> = specifier.chars().take(3).collect();
 
   if !specifier_chars.is_empty() && specifier_chars[0] == '.' {
     if specifier_len == 1 || specifier_chars[1] == '/' {
diff --git a/tests/integration/npm_tests.rs b/tests/integration/npm_tests.rs
index dba519087..e721633a6 100644
--- a/tests/integration/npm_tests.rs
+++ b/tests/integration/npm_tests.rs
@@ -15,13 +15,6 @@ use util::TestContextBuilder;
 
 // NOTE: See how to make test npm packages at ./testdata/npm/README.md
 
-itest!(esm_import_cjs_default {
-  args: "run --allow-read --allow-env --quiet --check=all npm/esm_import_cjs_default/main.ts",
-  output: "npm/esm_import_cjs_default/main.out",
-  envs: env_vars_for_npm_tests(),
-  http_server: true,
-});
-
 itest!(cjs_with_deps {
   args: "run --allow-read --allow-env npm/cjs_with_deps/main.js",
   output: "npm/cjs_with_deps/main.out",
@@ -324,14 +317,6 @@ itest!(check_local {
   exit_code: 1,
 });
 
-itest!(types_general {
-  args: "check --quiet npm/types/main.ts",
-  output: "npm/types/main.out",
-  envs: env_vars_for_npm_tests(),
-  http_server: true,
-  exit_code: 1,
-});
-
 itest!(types_ambient_module {
   args: "check --quiet npm/types_ambient_module/main.ts",
   output: "npm/types_ambient_module/main.out",
@@ -341,27 +326,11 @@ itest!(types_ambient_module {
 });
 
 itest!(types_ambient_module_import_map {
-    args: "check --quiet --import-map=npm/types_ambient_module/import_map.json npm/types_ambient_module/main_import_map.ts",
-    output: "npm/types_ambient_module/main_import_map.out",
-    envs: env_vars_for_npm_tests(),
-    http_server: true,
-    exit_code: 1,
-  });
-
-itest!(no_types_cjs {
-  args: "check --quiet npm/no_types_cjs/main.ts",
-  output_str: Some(""),
-  exit_code: 0,
-  envs: env_vars_for_npm_tests(),
-  http_server: true,
-});
-
-itest!(no_types_in_conditional_exports {
-  args: "run --check npm/no_types_in_conditional_exports/main.ts",
-  output: "npm/no_types_in_conditional_exports/main.out",
-  exit_code: 0,
+  args: "check --quiet --import-map=npm/types_ambient_module/import_map.json npm/types_ambient_module/main_import_map.ts",
+  output: "npm/types_ambient_module/main_import_map.out",
   envs: env_vars_for_npm_tests(),
   http_server: true,
+  exit_code: 1,
 });
 
 itest!(types_entry_value_not_exists {
diff --git a/tests/specs/node/byonm_phantom_dep_res_failure/__test__.jsonc b/tests/specs/node/byonm_phantom_dep_res_failure/__test__.jsonc
new file mode 100644
index 000000000..35e0a7686
--- /dev/null
+++ b/tests/specs/node/byonm_phantom_dep_res_failure/__test__.jsonc
@@ -0,0 +1,13 @@
+{
+  "tests": {
+    "bad_import": {
+      "args": "run bad_import.ts",
+      "output": "bad_import.out",
+      "exitCode": 1
+    },
+    "good_import": {
+      "args": "run good_import.ts",
+      "output": "good_import.out"
+    }
+  }
+}
diff --git a/tests/specs/node/byonm_phantom_dep_res_failure/bad_import.out b/tests/specs/node/byonm_phantom_dep_res_failure/bad_import.out
new file mode 100644
index 000000000..a524720e3
--- /dev/null
+++ b/tests/specs/node/byonm_phantom_dep_res_failure/bad_import.out
@@ -0,0 +1,2 @@
+error: [ERR_MODULE_NOT_FOUND] Cannot find module 'file:///[WILDLINE]/node_modules/package/index.js' imported from 'file:///[WILDLINE]/bad_import.ts'
+    at file:///[WILDLINE]/bad_import.ts:1:16
diff --git a/tests/specs/node/byonm_phantom_dep_res_failure/bad_import.ts b/tests/specs/node/byonm_phantom_dep_res_failure/bad_import.ts
new file mode 100644
index 000000000..e20fe1fcf
--- /dev/null
+++ b/tests/specs/node/byonm_phantom_dep_res_failure/bad_import.ts
@@ -0,0 +1,3 @@
+import hi from "package";
+
+hi();
diff --git a/tests/specs/node/byonm_phantom_dep_res_failure/deno.json b/tests/specs/node/byonm_phantom_dep_res_failure/deno.json
new file mode 100644
index 000000000..6134d86d1
--- /dev/null
+++ b/tests/specs/node/byonm_phantom_dep_res_failure/deno.json
@@ -0,0 +1,3 @@
+{
+  "unstable": ["byonm"]
+}
diff --git a/tests/specs/node/byonm_phantom_dep_res_failure/good_import.out b/tests/specs/node/byonm_phantom_dep_res_failure/good_import.out
new file mode 100644
index 000000000..45b983be3
--- /dev/null
+++ b/tests/specs/node/byonm_phantom_dep_res_failure/good_import.out
@@ -0,0 +1 @@
+hi
diff --git a/tests/specs/node/byonm_phantom_dep_res_failure/good_import.ts b/tests/specs/node/byonm_phantom_dep_res_failure/good_import.ts
new file mode 100644
index 000000000..2b17d3e33
--- /dev/null
+++ b/tests/specs/node/byonm_phantom_dep_res_failure/good_import.ts
@@ -0,0 +1,3 @@
+import hi from "package/main.js";
+
+hi();
diff --git a/tests/specs/node/byonm_phantom_dep_res_failure/node_modules/package/main.js b/tests/specs/node/byonm_phantom_dep_res_failure/node_modules/package/main.js
new file mode 100644
index 000000000..bc76b8e9e
--- /dev/null
+++ b/tests/specs/node/byonm_phantom_dep_res_failure/node_modules/package/main.js
@@ -0,0 +1 @@
+module.exports = () => console.log('hi');
\ No newline at end of file
diff --git a/tests/specs/node/byonm_phantom_dep_res_failure/node_modules/package/package.json b/tests/specs/node/byonm_phantom_dep_res_failure/node_modules/package/package.json
new file mode 100644
index 000000000..5723987e9
--- /dev/null
+++ b/tests/specs/node/byonm_phantom_dep_res_failure/node_modules/package/package.json
@@ -0,0 +1,4 @@
+{
+  "name": "package",
+  "version": "1.0.0"
+}
\ No newline at end of file
diff --git a/tests/specs/node/byonm_phantom_dep_res_failure/package.json b/tests/specs/node/byonm_phantom_dep_res_failure/package.json
new file mode 100644
index 000000000..2c63c0851
--- /dev/null
+++ b/tests/specs/node/byonm_phantom_dep_res_failure/package.json
@@ -0,0 +1,2 @@
+{
+}
diff --git a/tests/specs/npm/esm_import_cjs_default/__test__.jsonc b/tests/specs/npm/esm_import_cjs_default/__test__.jsonc
new file mode 100644
index 000000000..b2a25914f
--- /dev/null
+++ b/tests/specs/npm/esm_import_cjs_default/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --allow-read --allow-env --check=all main.ts",
+  "output": "main.out"
+}
diff --git a/tests/testdata/npm/esm_import_cjs_default/main.out b/tests/specs/npm/esm_import_cjs_default/main.out
index 0f6a61e34..ec7962e5a 100644
--- a/tests/testdata/npm/esm_import_cjs_default/main.out
+++ b/tests/specs/npm/esm_import_cjs_default/main.out
@@ -1,3 +1,10 @@
+[UNORDERED_START]
+Download http://localhost:4260/@denotest/esm-import-cjs-default
+Download http://localhost:4260/@denotest/cjs-default-export
+Download http://localhost:4260/@denotest/cjs-default-export/1.0.0.tgz
+Download http://localhost:4260/@denotest/esm-import-cjs-default/1.0.0.tgz
+[UNORDERED_END]
+Check file:///[WILDLINE]/main.ts
 Node esm importing node cjs
 ===========================
 {
diff --git a/tests/testdata/npm/esm_import_cjs_default/main.ts b/tests/specs/npm/esm_import_cjs_default/main.ts
index f9c3280e5..f9c3280e5 100644
--- a/tests/testdata/npm/esm_import_cjs_default/main.ts
+++ b/tests/specs/npm/esm_import_cjs_default/main.ts
diff --git a/tests/specs/npm/no_types_cjs/__test__.jsonc b/tests/specs/npm/no_types_cjs/__test__.jsonc
new file mode 100644
index 000000000..de0339cfb
--- /dev/null
+++ b/tests/specs/npm/no_types_cjs/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "check main.ts",
+  "output": "main.out"
+}
diff --git a/tests/specs/npm/no_types_cjs/main.out b/tests/specs/npm/no_types_cjs/main.out
new file mode 100644
index 000000000..4747a9a32
--- /dev/null
+++ b/tests/specs/npm/no_types_cjs/main.out
@@ -0,0 +1,3 @@
+Download http://localhost:4260/@denotest/no-types-cjs
+Download http://localhost:4260/@denotest/no-types-cjs/1.0.0.tgz
+Check file:///[WILDLINE]/no_types_cjs/main.ts
diff --git a/tests/testdata/npm/no_types_cjs/main.ts b/tests/specs/npm/no_types_cjs/main.ts
index 32458e839..32458e839 100644
--- a/tests/testdata/npm/no_types_cjs/main.ts
+++ b/tests/specs/npm/no_types_cjs/main.ts
diff --git a/tests/specs/npm/no_types_in_conditional_exports/__test__.jsonc b/tests/specs/npm/no_types_in_conditional_exports/__test__.jsonc
new file mode 100644
index 000000000..8955fcda2
--- /dev/null
+++ b/tests/specs/npm/no_types_in_conditional_exports/__test__.jsonc
@@ -0,0 +1,4 @@
+{
+  "args": "run --check main.ts",
+  "output": "main.out"
+}
diff --git a/tests/testdata/npm/no_types_in_conditional_exports/main.out b/tests/specs/npm/no_types_in_conditional_exports/main.out
index 46c583234..46c583234 100644
--- a/tests/testdata/npm/no_types_in_conditional_exports/main.out
+++ b/tests/specs/npm/no_types_in_conditional_exports/main.out
diff --git a/tests/testdata/npm/no_types_in_conditional_exports/main.ts b/tests/specs/npm/no_types_in_conditional_exports/main.ts
index 7ec2f18fd..7ec2f18fd 100644
--- a/tests/testdata/npm/no_types_in_conditional_exports/main.ts
+++ b/tests/specs/npm/no_types_in_conditional_exports/main.ts
diff --git a/tests/specs/npm/types_general/__test__.jsonc b/tests/specs/npm/types_general/__test__.jsonc
new file mode 100644
index 000000000..a991c6eed
--- /dev/null
+++ b/tests/specs/npm/types_general/__test__.jsonc
@@ -0,0 +1,5 @@
+{
+  "args": "check main.ts",
+  "output": "main.out",
+  "exitCode": 1
+}
diff --git a/tests/testdata/npm/types/main.out b/tests/specs/npm/types_general/main.out
index de1f2c145..ffba4f84d 100644
--- a/tests/testdata/npm/types/main.out
+++ b/tests/specs/npm/types_general/main.out
@@ -1,7 +1,16 @@
+[UNORDERED_START]
+Download http://localhost:4260/@denotest/types
+Download http://localhost:4260/@denotest/types_imported
+Download http://localhost:4260/@denotest/types-exports-subpaths
+Download http://localhost:4260/@denotest/types_imported/1.0.0.tgz
+Download http://localhost:4260/@denotest/types-exports-subpaths/1.0.0.tgz
+Download http://localhost:4260/@denotest/types/1.0.0.tgz
+[UNORDERED_END]
+Check file:///[WILDLINE]/main.ts
 error: TS2322 [ERROR]: Type 'number' is not assignable to type 'string'.
   bar: 1,
   ~~~
-    at [WILDCARD]/npm/types/main.ts:[WILDCARD]
+    at [WILDCARD]/main.ts:[WILDCARD]
 
     The expected type comes from property 'bar' which is declared here on type 'Foobar'
         bar: string;
@@ -11,7 +20,7 @@ error: TS2322 [ERROR]: Type 'number' is not assignable to type 'string'.
 TS2322 [ERROR]: Type 'number' is not assignable to type 'string'.
   prop: 1,
   ~~~~
-    at [WILDCARD]/npm/types/main.ts:[WILDCARD]
+    at [WILDCARD]/main.ts:[WILDCARD]
 
     The expected type comes from property 'prop' which is declared here on type 'SomeInterface'
         prop: string;
@@ -21,7 +30,7 @@ TS2322 [ERROR]: Type 'number' is not assignable to type 'string'.
 TS2322 [ERROR]: Type 'string' is not assignable to type 'number'.
   prop2: "asdf",
   ~~~~~
-    at [WILDCARD]/npm/types/main.ts:[WILDCARD]
+    at [WILDCARD]/main.ts:[WILDCARD]
 
     The expected type comes from property 'prop2' which is declared here on type 'SomeInterface'
         prop2: number;
@@ -31,7 +40,7 @@ TS2322 [ERROR]: Type 'string' is not assignable to type 'number'.
 TS2322 [ERROR]: Type 'number' is not assignable to type 'string'.
   fizz: 1,
   ~~~~
-    at [WILDCARD]/npm/types/main.ts:[WILDCARD]
+    at [WILDCARD]/main.ts:[WILDCARD]
 
     The expected type comes from property 'fizz' which is declared here on type 'Fizzbuzz'
       fizz: string;
@@ -41,7 +50,7 @@ TS2322 [ERROR]: Type 'number' is not assignable to type 'string'.
 TS2322 [ERROR]: Type 'number' is not assignable to type 'string'.
   buzz: 2,
   ~~~~
-    at [WILDCARD]/npm/types/main.ts:[WILDCARD]
+    at [WILDCARD]/main.ts:[WILDCARD]
 
     The expected type comes from property 'buzz' which is declared here on type 'Fizzbuzz'
       buzz: string;
@@ -51,21 +60,21 @@ TS2322 [ERROR]: Type 'number' is not assignable to type 'string'.
 TS2322 [ERROR]: Type '5' is not assignable to type '"test1"'.
 const valueA: "test1" = getClient();
       ~~~~~~
-    at [WILDCARD]/npm/types/main.ts:[WILDCARD]
+    at [WILDCARD]/main.ts:[WILDCARD]
 
 TS2322 [ERROR]: Type '"import"' is not assignable to type '"test2"'.
 const valueB: "test2" = entryImport();
       ~~~~~~
-    at [WILDCARD]/types/main.ts:[WILDCARD]
+    at [WILDCARD]/main.ts:[WILDCARD]
 
 TS2322 [ERROR]: Type '12' is not assignable to type '"test3"'.
 const valueC: "test3" = entryA();
       ~~~~~~
-    at [WILDCARD]/types/main.ts:[WILDCARD]
+    at [WILDCARD]/main.ts:[WILDCARD]
 
 TS2322 [ERROR]: Type '"types"' is not assignable to type '"test4"'.
 const valueD: "test4" = entryTypes();
       ~~~~~~
-    at file:///[WILDCARD]/types/main.ts:[WILDCARD]
+    at file:///[WILDCARD]/main.ts:[WILDCARD]
 
 Found 9 errors.
diff --git a/tests/testdata/npm/types/main.ts b/tests/specs/npm/types_general/main.ts
index ae420f6d6..ae420f6d6 100644
--- a/tests/testdata/npm/types/main.ts
+++ b/tests/specs/npm/types_general/main.ts
diff --git a/tools/lint.js b/tools/lint.js
index aeab48c1a..dad963160 100755
--- a/tools/lint.js
+++ b/tools/lint.js
@@ -218,7 +218,7 @@ async function ensureNoNewITests() {
     "lsp_tests.rs": 0,
     "node_compat_tests.rs": 4,
     "node_unit_tests.rs": 2,
-    "npm_tests.rs": 97,
+    "npm_tests.rs": 93,
     "pm_tests.rs": 0,
     "publish_tests.rs": 0,
     "repl_tests.rs": 0,