fix(ext/node): implement crypto.Sign (RSA/PEM/SHA{224,256,384,512}) (#18471)

9 files changed, 165 insertions, 18 deletions

diff --git a/Cargo.lock b/Cargo.lock
index a0cf367ac..f28c00b55 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -1167,6 +1167,7 @@ dependencies = [
  "sha-1 0.10.0",
  "sha2",
  "sha3",
+ "signature",
  "tokio",
  "typenum",
 ]
diff --git a/Cargo.toml b/Cargo.toml
index 1af05645c..b4ee768be 100644
--- a/Cargo.toml
+++ b/Cargo.toml
@@ -121,6 +121,7 @@ serde_bytes = "0.11"
 serde_json = "1.0.85"
 serde_repr = "=0.1.9"
 sha2 = { version = "0.10.6", features = ["oid"] }
+signature = "=1.6.4"
 smallvec = "1.8"
 socket2 = "0.4.7"
 tar = "=0.4.38"
@@ -136,7 +137,7 @@ uuid = { version = "1.3.0", features = ["v4"] }
 zstd = "=0.11.2"
 
 # crypto
-rsa = { version = "0.7.0", default-features = false, features = ["std", "pem"] }
+rsa = { version = "0.7.0", default-features = false, features = ["std", "pem", "hazmat"] } # hazmat needed for PrehashSigner in ext/node
 
 # macros
 proc-macro2 = "1"
diff --git a/cli/tests/unit_node/crypto_sign_test.ts b/cli/tests/unit_node/crypto_sign_test.ts
new file mode 100644
index 000000000..1d3d2b3ec
--- /dev/null
+++ b/cli/tests/unit_node/crypto_sign_test.ts
@@ -0,0 +1,47 @@
+// Copyright 2018-2023 the Deno authors. All rights reserved. MIT license.
+
+import { assertEquals } from "../../../test_util/std/testing/asserts.ts";
+import { createSign } from "node:crypto";
+import { Buffer } from "node:buffer";
+
+const rsaPrivatePem = Buffer.from(
+  await Deno.readFile(
+    new URL("./testdata/rsa_private.pem", import.meta.url),
+  ),
+);
+
+Deno.test({
+  name: "crypto.Sign - RSA PEM with SHA224, SHA256, SHA384, SHA512 digests",
+  fn() {
+    const table = [
+      {
+        algorithms: ["sha224", "RSA-SHA224"],
+        expected:
+          "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",
+      },
+      {
+        algorithms: ["sha256", "RSA-SHA256"],
+        expected:
+          "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",
+      },
+      {
+        algorithms: ["sha384", "RSA-SHA384"],
+        expected:
+          "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",
+      },
+      {
+        algorithms: ["sha512", "RSA-SHA512"],
+        expected:
+          "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",
+      },
+    ];
+
+    for (const testCase of table) {
+      for (const algorithm of testCase.algorithms) {
+        const signature = createSign(algorithm).update("some data to sign")
+          .sign(rsaPrivatePem, "hex");
+        assertEquals(signature, testCase.expected);
+      }
+    }
+  },
+});
diff --git a/ext/crypto/Cargo.toml b/ext/crypto/Cargo.toml
index 8313f0089..c9fa4be53 100644
--- a/ext/crypto/Cargo.toml
+++ b/ext/crypto/Cargo.toml
@@ -39,7 +39,7 @@ serde.workspace = true
 serde_bytes.workspace = true
 sha1 = { version = "0.10.5", features = ["oid"] }
 sha2.workspace = true
-signature = "1.6.4"
+signature.workspace = true
 spki = "0.6.0"
 tokio.workspace = true
 uuid.workspace = true
diff --git a/ext/node/Cargo.toml b/ext/node/Cargo.toml
index d0a5a40fb..be3231087 100644
--- a/ext/node/Cargo.toml
+++ b/ext/node/Cargo.toml
@@ -39,5 +39,6 @@ serde = "1.0.149"
 sha-1 = "0.10.0"
 sha2 = "0.10.6"
 sha3 = "0.10.5"
+signature.workspace = true
 tokio.workspace = true
 typenum = "1.15.0"
diff --git a/ext/node/crypto/mod.rs b/ext/node/crypto/mod.rs
index 352d9c31a..3529a3aa4 100644
--- a/ext/node/crypto/mod.rs
+++ b/ext/node/crypto/mod.rs
@@ -290,6 +290,64 @@ pub fn op_node_decipheriv_final(
   context.r#final(input, output)
 }
 
+#[op]
+pub fn op_node_sign(
+  digest: &[u8],
+  digest_type: &str,
+  key: StringOrBuffer,
+  key_type: &str,
+  key_format: &str,
+) -> Result<ZeroCopyBuf, AnyError> {
+  match key_type {
+    "rsa" => {
+      use rsa::pkcs1v15::SigningKey;
+      use signature::hazmat::PrehashSigner;
+      let key = match key_format {
+        "pem" => RsaPrivateKey::from_pkcs8_pem((&key).try_into()?)
+          .map_err(|_| type_error("Invalid RSA key"))?,
+        // TODO(kt3k): Support der and jwk formats
+        _ => {
+          return Err(type_error(format!(
+            "Unsupported key format: {}",
+            key_format
+          )))
+        }
+      };
+      Ok(
+        match digest_type {
+          "sha224" => {
+            let signing_key = SigningKey::<sha2::Sha224>::new_with_prefix(key);
+            signing_key.sign_prehash(digest)?.to_vec()
+          }
+          "sha256" => {
+            let signing_key = SigningKey::<sha2::Sha256>::new_with_prefix(key);
+            signing_key.sign_prehash(digest)?.to_vec()
+          }
+          "sha384" => {
+            let signing_key = SigningKey::<sha2::Sha384>::new_with_prefix(key);
+            signing_key.sign_prehash(digest)?.to_vec()
+          }
+          "sha512" => {
+            let signing_key = SigningKey::<sha2::Sha512>::new_with_prefix(key);
+            signing_key.sign_prehash(digest)?.to_vec()
+          }
+          _ => {
+            return Err(type_error(format!(
+              "Unknown digest algorithm: {}",
+              digest_type
+            )))
+          }
+        }
+        .into(),
+      )
+    }
+    _ => Err(type_error(format!(
+      "Signing with {} keys is not supported yet",
+      key_type
+    ))),
+  }
+}
+
 fn pbkdf2_sync(
   password: &[u8],
   salt: &[u8],
diff --git a/ext/node/lib.rs b/ext/node/lib.rs
index b83a86a5b..0507f4a88 100644
--- a/ext/node/lib.rs
+++ b/ext/node/lib.rs
@@ -119,6 +119,7 @@ deno_core::extension!(deno_node,
     crypto::op_node_check_prime_bytes_async,
     crypto::op_node_pbkdf2,
     crypto::op_node_pbkdf2_async,
+    crypto::op_node_sign,
     winerror::op_node_sys_to_uv_error,
     v8::op_v8_cached_data_version_tag,
     v8::op_v8_get_heap_statistics,
@@ -406,7 +407,7 @@ pub fn initialize_runtime(
   let source_code = format!(
     r#"(function loadBuiltinNodeModules(nodeGlobalThisName, usesLocalNodeModulesDir, argv0) {{
       Deno[Deno.internal].node.initialize(
-        nodeGlobalThisName, 
+        nodeGlobalThisName,
         usesLocalNodeModulesDir,
         argv0
       );
diff --git a/ext/node/polyfills/internal/crypto/hash.ts b/ext/node/polyfills/internal/crypto/hash.ts
index 63c92190c..00dfa19af 100644
--- a/ext/node/polyfills/internal/crypto/hash.ts
+++ b/ext/node/polyfills/internal/crypto/hash.ts
@@ -73,7 +73,7 @@ export class Hash extends Transform {
 
     if (typeof algorithm === "string") {
       this.#context = ops.op_node_create_hash(
-        algorithm,
+        algorithm.toLowerCase(),
       );
       if (this.#context === 0) {
         throw new TypeError(`Unknown hash algorithm: ${algorithm}`);
diff --git a/ext/node/polyfills/internal/crypto/sig.ts b/ext/node/polyfills/internal/crypto/sig.ts
index d61f82b0e..e49128b1e 100644
--- a/ext/node/polyfills/internal/crypto/sig.ts
+++ b/ext/node/polyfills/internal/crypto/sig.ts
@@ -14,6 +14,12 @@ import type {
   PublicKeyInput,
 } from "ext:deno_node/internal/crypto/types.ts";
 import { KeyObject } from "ext:deno_node/internal/crypto/keys.ts";
+import { createHash, Hash } from "ext:deno_node/internal/crypto/hash.ts";
+import { KeyFormat, KeyType } from "ext:deno_node/internal/crypto/types.ts";
+import { isArrayBufferView } from "ext:deno_node/internal/util/types.ts";
+
+const { core } = globalThis.__bootstrap;
+const { ops } = core;
 
 export type DSAEncoding = "der" | "ieee-p1363";
 
@@ -37,30 +43,62 @@ export interface VerifyKeyObjectInput extends SigningOptions {
 export type KeyLike = string | Buffer | KeyObject;
 
 export class Sign extends Writable {
+  hash: Hash;
+  #digestType: string;
+
   constructor(algorithm: string, _options?: WritableOptions) {
     validateString(algorithm, "algorithm");
 
-    super();
-
-    notImplemented("crypto.Sign");
+    super({
+      write(chunk, enc, callback) {
+        this.update(chunk, enc);
+        callback();
+      },
+    });
+
+    algorithm = algorithm.toLowerCase();
+
+    if (algorithm.startsWith("rsa-")) {
+      // Allows RSA-[digest_algorithm] as a valid algorithm
+      algorithm = algorithm.slice(4);
+    }
+    this.#digestType = algorithm;
+    this.hash = createHash(this.#digestType);
   }
 
-  sign(privateKey: KeyLike | SignKeyObjectInput | SignPrivateKeyInput): Buffer;
   sign(
     privateKey: KeyLike | SignKeyObjectInput | SignPrivateKeyInput,
-    outputFormat: BinaryToTextEncoding,
-  ): string;
-  sign(
-    _privateKey: KeyLike | SignKeyObjectInput | SignPrivateKeyInput,
-    _outputEncoding?: BinaryToTextEncoding,
+    encoding?: BinaryToTextEncoding,
   ): Buffer | string {
-    notImplemented("crypto.Sign.prototype.sign");
+    let keyData: Uint8Array;
+    let keyType: KeyType;
+    let keyFormat: KeyFormat;
+    if (typeof privateKey === "string" || isArrayBufferView(privateKey)) {
+      // if the key is BinaryLike, interpret it as a PEM encoded RSA key
+      keyData = privateKey;
+      keyType = "rsa";
+      keyFormat = "pem";
+    } else {
+      // TODO(kt3k): Add support for the case when privateKey is a KeyObject,
+      // CryptoKey, etc
+      notImplemented("crypto.Sign.prototype.sign with non BinaryLike input");
+    }
+    const ret = Buffer.from(ops.op_node_sign(
+      this.hash.digest(),
+      this.#digestType,
+      keyData!,
+      keyType,
+      keyFormat,
+    ));
+    return encoding ? ret.toString(encoding) : ret;
   }
 
-  update(data: BinaryLike): this;
-  update(data: string, inputEncoding: Encoding): this;
-  update(_data: BinaryLike | string, _inputEncoding?: Encoding): this {
-    notImplemented("crypto.Sign.prototype.update");
+  update(
+    data: BinaryLike | string,
+    encoding?: Encoding,
+  ): this {
+    this.hash.update(data, encoding);
+    return this;
   }
 }