9 files changed, 67 insertions, 9 deletions
diff --git a/Cargo.lock b/Cargo.lock
index d7feda5e6..d2202a7e7 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -2060,9 +2060,9 @@ dependencies = [
 
 [[package]]
 name = "deno_unsync"
-version = "0.4.0"
+version = "0.4.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "03ee1607db298c8f12124b345a52d5f2f504a7504c9d535f1d8f07127b237010"
+checksum = "2f36b4ef61a04ce201b925a5dffa90f88437d37fee4836c758470dd15ba7f05e"
 dependencies = [
  "parking_lot 0.12.3",
  "tokio",
diff --git a/cli/mainrt.rs b/cli/mainrt.rs
index fd03224be..02d58fcee 100644
--- a/cli/mainrt.rs
+++ b/cli/mainrt.rs
@@ -83,6 +83,7 @@ fn load_env_vars(env_vars: &IndexMap<String, String>) {
 }
 
 fn main() {
+  deno_runtime::deno_permissions::mark_standalone();
   let args: Vec<_> = env::args_os().collect();
   let standalone = standalone::extract_standalone(Cow::Owned(args));
   let future = async move {
diff --git a/ext/fs/ops.rs b/ext/fs/ops.rs
index 57b0e0b9e..e8a074be5 100644
--- a/ext/fs/ops.rs
+++ b/ext/fs/ops.rs
@@ -67,7 +67,14 @@ fn map_permission_error(
       } else {
         (path.as_str(), "")
       };
-      custom_error("PermissionDenied", format!("Requires {err} access to {path}{truncated}, run again with the --allow-{err} flag"))
+      let msg = if deno_permissions::is_standalone() {
+        format!(
+          "Requires {err} access to {path}{truncated}, specify the required permissions during compilation using `deno compile --allow-{err}`")
+      } else {
+        format!(
+          "Requires {err} access to {path}{truncated}, run again with the --allow-{err} flag")
+      };
+      custom_error("PermissionDenied", msg)
     }
     err => Err::<(), _>(err)
       .context_path(operation, path)
diff --git a/runtime/permissions/lib.rs b/runtime/permissions/lib.rs
index b0fa9eb10..55a94d909 100644
--- a/runtime/permissions/lib.rs
+++ b/runtime/permissions/lib.rs
@@ -12,6 +12,7 @@ use deno_core::serde::Deserialize;
 use deno_core::serde::Deserializer;
 use deno_core::serde::Serialize;
 use deno_core::serde_json;
+use deno_core::unsync::sync::AtomicFlag;
 use deno_core::url;
 use deno_core::url::Url;
 use deno_core::ModuleSpecifier;
@@ -132,14 +133,20 @@ impl PermissionState {
   }
 
   fn error(name: &str, info: impl FnOnce() -> Option<String>) -> AnyError {
-    custom_error(
-      "PermissionDenied",
+    let msg = if is_standalone() {
+      format!(
+        "Requires {}, specify the required permissions during compilation using `deno compile --allow-{}`",
+        Self::fmt_access(name, info),
+        name
+      )
+    } else {
       format!(
         "Requires {}, run again with the --allow-{} flag",
         Self::fmt_access(name, info),
         name
-      ),
-    )
+      )
+    };
+    custom_error("PermissionDenied", msg)
   }
 
   /// Check the permission state. bool is whether a prompt was issued.
@@ -2313,6 +2320,16 @@ pub fn create_child_permissions(
   Ok(worker_perms)
 }
 
+static IS_STANDALONE: AtomicFlag = AtomicFlag::lowered();
+
+pub fn mark_standalone() {
+  IS_STANDALONE.raise();
+}
+
+pub fn is_standalone() -> bool {
+  IS_STANDALONE.is_raised()
+}
+
 #[cfg(test)]
 mod tests {
   use super::*;
diff --git a/runtime/permissions/prompter.rs b/runtime/permissions/prompter.rs
index 050902d59..e48e0af10 100644
--- a/runtime/permissions/prompter.rs
+++ b/runtime/permissions/prompter.rs
@@ -11,6 +11,8 @@ use std::io::StderrLock;
 use std::io::StdinLock;
 use std::io::Write as IoWrite;
 
+use crate::is_standalone;
+
 /// Helper function to make control characters visible so users can see the underlying filename.
 fn escape_control_characters(s: &str) -> std::borrow::Cow<str> {
   if !s.contains(|c: char| c.is_ascii_control() || c.is_control()) {
@@ -339,7 +341,11 @@ impl PermissionPrompter for TtyPrompter {
         ))
       );
       writeln!(&mut output, "┠─ {}", colors::italic(&msg)).unwrap();
-      let msg = format!("Run again with --allow-{name} to bypass this prompt.");
+      let msg = if is_standalone() {
+        format!("Specify the required permissions during compile time using `deno compile --allow-{name}`.")
+      } else {
+        format!("Run again with --allow-{name} to bypass this prompt.")
+      };
       writeln!(&mut output, "┠─ {}", colors::italic(&msg)).unwrap();
       write!(&mut output, "┗ {}", colors::bold("Allow?")).unwrap();
       write!(&mut output, " {opts} > ").unwrap();
diff --git a/tests/specs/compile/permissions_denied/__test__.jsonc b/tests/specs/compile/permissions_denied/__test__.jsonc
new file mode 100644
index 000000000..8f8590162
--- /dev/null
+++ b/tests/specs/compile/permissions_denied/__test__.jsonc
@@ -0,0 +1,24 @@
+{
+  "tempDir": true,
+  "steps": [{
+    "if": "unix",
+    "args": "compile --output main main.ts",
+    "output": "[WILDCARD]"
+  }, {
+    "if": "unix",
+    "commandName": "./main",
+    "args": [],
+    "exitCode": 1,
+    "output": "main.out"
+  }, {
+    "if": "windows",
+    "args": "compile --output main.exe main.ts",
+    "output": "[WILDCARD]"
+  }, {
+    "if": "windows",
+    "commandName": "./main.exe",
+    "args": [],
+    "exitCode": 1,
+    "output": "main.out"
+  }]
+}
diff --git a/tests/specs/compile/permissions_denied/main.out b/tests/specs/compile/permissions_denied/main.out
new file mode 100644
index 000000000..e9ea45c81
--- /dev/null
+++ b/tests/specs/compile/permissions_denied/main.out
@@ -0,0 +1,2 @@
+error: Uncaught (in promise) PermissionDenied: Requires run access to "deno", specify the required permissions during compilation using `deno compile --allow-run`
+[WILDCARD]
+\ No newline at end of file
diff --git a/tests/specs/compile/permissions_denied/main.ts b/tests/specs/compile/permissions_denied/main.ts
new file mode 100644
index 000000000..eeac858ff
--- /dev/null
+++ b/tests/specs/compile/permissions_denied/main.ts
@@ -0,0 +1 @@
+new Deno.Command("deno").outputSync();
diff --git a/tests/testdata/npm/deno_run_cowsay_no_permissions.out b/tests/testdata/npm/deno_run_cowsay_no_permissions.out
index 206ef1484..837394d49 100644
--- a/tests/testdata/npm/deno_run_cowsay_no_permissions.out
+++ b/tests/testdata/npm/deno_run_cowsay_no_permissions.out
@@ -1,2 +1,2 @@
-error: Uncaught PermissionDenied: Requires read access to <CWD>, run again with the --allow-read flag
+error: Uncaught PermissionDenied: Requires read access to <CWD>, specify the required permissions during compilation using `deno compile --allow-read`
 [WILDCARD]