diff --git a/.github/workflows/ci.generate.ts b/.github/workflows/ci.generate.ts
index 5bf55f62b4..241b38ef99 100755
--- a/.github/workflows/ci.generate.ts
+++ b/.github/workflows/ci.generate.ts
@@ -17,7 +17,7 @@ const Runners = (() => {
 })();
 // bump the number at the start when you want to purge the cache
 const prCacheKeyPrefix =
-  "19-cargo-target-${{ matrix.os }}-${{ matrix.profile }}-${{ matrix.job }}-";
+  "20-cargo-target-${{ matrix.os }}-${{ matrix.profile }}-${{ matrix.job }}-";
 
 const installPkgsCommand =
   "sudo apt-get install --no-install-recommends debootstrap clang-15 lld-15";
diff --git a/.github/workflows/ci.yml b/.github/workflows/ci.yml
index b0dab622aa..c7144164b6 100644
--- a/.github/workflows/ci.yml
+++ b/.github/workflows/ci.yml
@@ -302,7 +302,7 @@ jobs:
             !./target/*/*.zip
             !./target/*/*.tar.gz
           key: never_saved
-          restore-keys: '19-cargo-target-${{ matrix.os }}-${{ matrix.profile }}-${{ matrix.job }}-'
+          restore-keys: '20-cargo-target-${{ matrix.os }}-${{ matrix.profile }}-${{ matrix.job }}-'
       - name: Apply and update mtime cache
         if: '!(github.event_name == ''pull_request'' && matrix.skip_pr) && (!startsWith(github.ref, ''refs/tags/''))'
         uses: ./.github/mtime_cache
@@ -578,7 +578,7 @@ jobs:
             !./target/*/gn_out
             !./target/*/*.zip
             !./target/*/*.tar.gz
-          key: '19-cargo-target-${{ matrix.os }}-${{ matrix.profile }}-${{ matrix.job }}-${{ github.sha }}'
+          key: '20-cargo-target-${{ matrix.os }}-${{ matrix.profile }}-${{ matrix.job }}-${{ github.sha }}'
   publish-canary:
     name: publish canary
     runs-on: ubuntu-22.04
diff --git a/Cargo.lock b/Cargo.lock
index c24f96cf3e..f301625015 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -927,8 +927,8 @@ dependencies = [
  "serde_bytes",
  "sha1",
  "sha2",
- "signature",
- "spki",
+ "signature 1.6.4",
+ "spki 0.6.0",
  "tokio",
  "uuid",
  "x25519-dalek",
@@ -1152,6 +1152,7 @@ dependencies = [
  "data-encoding",
  "deno_core",
  "digest 0.10.6",
+ "dsa",
  "ecb",
  "hex",
  "hkdf",
@@ -1162,6 +1163,7 @@ dependencies = [
  "md-5",
  "md4",
  "num-bigint",
+ "num-bigint-dig",
  "num-integer",
  "num-traits",
  "once_cell",
@@ -1169,6 +1171,7 @@ dependencies = [
  "pbkdf2",
  "rand",
  "regex",
+ "ring",
  "ripemd",
  "rsa",
  "scrypt",
@@ -1176,9 +1179,10 @@ dependencies = [
  "sha-1 0.10.0",
  "sha2",
  "sha3",
- "signature",
+ "signature 1.6.4",
  "tokio",
  "typenum",
+ "x25519-dalek",
  "x509-parser",
 ]
 
@@ -1386,6 +1390,16 @@ dependencies = [
  "zeroize",
 ]
 
+[[package]]
+name = "der"
+version = "0.7.3"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "82b10af9f9f9f2134a42d3f8aa74658660f2e0234b0eb81bd171df8aa32779ed"
+dependencies = [
+ "const-oid",
+ "zeroize",
+]
+
 [[package]]
 name = "der-parser"
 version = "8.2.0"
@@ -1565,6 +1579,22 @@ dependencies = [
  "text_lines",
 ]
 
+[[package]]
+name = "dsa"
+version = "0.6.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "b5638f6d17447bc0ffc46354949ee366847e83450e2a07895862942085cc9761"
+dependencies = [
+ "digest 0.10.6",
+ "num-bigint-dig",
+ "num-traits",
+ "pkcs8 0.10.2",
+ "rfc6979 0.4.0",
+ "sha2",
+ "signature 2.1.0",
+ "zeroize",
+]
+
 [[package]]
 name = "dyn-clone"
 version = "1.0.11"
@@ -1612,10 +1642,10 @@ version = "0.14.8"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "413301934810f597c1d19ca71c8710e99a3f1ba28a0d2ebc01551a2daeea3c5c"
 dependencies = [
- "der",
+ "der 0.6.1",
  "elliptic-curve",
- "rfc6979",
- "signature",
+ "rfc6979 0.3.1",
+ "signature 1.6.4",
 ]
 
 [[package]]
@@ -1632,14 +1662,14 @@ checksum = "e7bb888ab5300a19b8e5bceef25ac745ad065f3c9f7efc6de1b91958110891d3"
 dependencies = [
  "base16ct",
  "crypto-bigint",
- "der",
+ "der 0.6.1",
  "digest 0.10.6",
  "ff",
  "generic-array 0.14.6",
  "group",
  "hkdf",
  "pem-rfc7468",
- "pkcs8",
+ "pkcs8 0.9.0",
  "rand_core 0.6.4",
  "sec1",
  "subtle",
@@ -2976,6 +3006,7 @@ dependencies = [
  "num-iter",
  "num-traits",
  "rand",
+ "serde",
  "smallvec",
  "zeroize",
 ]
@@ -3307,9 +3338,9 @@ version = "0.4.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "eff33bdbdfc54cc98a2eca766ebdec3e1b8fb7387523d5c9c9a2891da856f719"
 dependencies = [
- "der",
- "pkcs8",
- "spki",
+ "der 0.6.1",
+ "pkcs8 0.9.0",
+ "spki 0.6.0",
  "zeroize",
 ]
 
@@ -3319,8 +3350,18 @@ version = "0.9.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "9eca2c590a5f85da82668fa685c09ce2888b9430e83299debf1f34b65fd4a4ba"
 dependencies = [
- "der",
- "spki",
+ "der 0.6.1",
+ "spki 0.6.0",
+]
+
+[[package]]
+name = "pkcs8"
+version = "0.10.2"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "f950b2377845cebe5cf8b5165cb3cc1a5e0fa5cfa3e1f7f55707d8fd82e0a7b7"
+dependencies = [
+ "der 0.7.3",
+ "spki 0.7.1",
 ]
 
 [[package]]
@@ -3649,6 +3690,16 @@ dependencies = [
  "zeroize",
 ]
 
+[[package]]
+name = "rfc6979"
+version = "0.4.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "f8dd2a808d456c4a54e300a23e9f5a67e122c3024119acbfd73e3bf664491cb2"
+dependencies = [
+ "hmac",
+ "subtle",
+]
+
 [[package]]
 name = "ring"
 version = "0.16.20"
@@ -3686,9 +3737,9 @@ dependencies = [
  "num-iter",
  "num-traits",
  "pkcs1",
- "pkcs8",
+ "pkcs8 0.9.0",
  "rand_core 0.6.4",
- "signature",
+ "signature 1.6.4",
  "smallvec",
  "subtle",
  "zeroize",
@@ -3901,9 +3952,9 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "3be24c1842290c45df0a7bf069e0c268a747ad05a192f2fd7dcfdbc1cba40928"
 dependencies = [
  "base16ct",
- "der",
+ "der 0.6.1",
  "generic-array 0.14.6",
- "pkcs8",
+ "pkcs8 0.9.0",
  "subtle",
  "zeroize",
 ]
@@ -4123,6 +4174,16 @@ dependencies = [
  "rand_core 0.6.4",
 ]
 
+[[package]]
+name = "signature"
+version = "2.1.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "5e1788eed21689f9cf370582dfc467ef36ed9c707f073528ddafa8d83e3b8500"
+dependencies = [
+ "digest 0.10.6",
+ "rand_core 0.6.4",
+]
+
 [[package]]
 name = "simdutf8"
 version = "0.1.4"
@@ -4199,7 +4260,17 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "67cf02bbac7a337dc36e4f5a693db6c21e7863f45070f7064577eb4367a3212b"
 dependencies = [
  "base64ct",
- "der",
+ "der 0.6.1",
+]
+
+[[package]]
+name = "spki"
+version = "0.7.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "37a5be806ab6f127c3da44b7378837ebf01dadca8510a0e572460216b228bd0e"
+dependencies = [
+ "base64ct",
+ "der 0.7.3",
 ]
 
 [[package]]
diff --git a/cli/tests/unit_node/crypto_key.ts b/cli/tests/unit_node/crypto_key.ts
index d1a33db9e5..49d81003f0 100644
--- a/cli/tests/unit_node/crypto_key.ts
+++ b/cli/tests/unit_node/crypto_key.ts
@@ -1,9 +1,39 @@
+// deno-lint-ignore-file no-explicit-any
+
 // Copyright 2018-2023 the Deno authors. All rights reserved. MIT license.
-import { createSecretKey, randomBytes } from "node:crypto";
+import {
+  createSecretKey,
+  generateKeyPair,
+  generateKeyPairSync,
+  KeyObject,
+  randomBytes,
+} from "node:crypto";
+import { promisify } from "node:util";
 import { Buffer } from "node:buffer";
-import { assertEquals } from "../../../test_util/std/testing/asserts.ts";
+import {
+  assertEquals,
+  assertThrows,
+} from "../../../test_util/std/testing/asserts.ts";
 import { createHmac } from "node:crypto";
 
+const generateKeyPairAsync = promisify(
+  (
+    type: any,
+    options: any,
+    callback: (
+      err: Error | null,
+      key: { publicKey: KeyObject; privateKey: KeyObject },
+    ) => void,
+  ) =>
+    generateKeyPair(
+      type,
+      options,
+      (err: Error | null, publicKey: KeyObject, privateKey: KeyObject) => {
+        callback(err, { publicKey, privateKey });
+      },
+    ),
+);
+
 Deno.test({
   name: "create secret key",
   fn() {
@@ -45,3 +75,130 @@ Deno.test({
     );
   },
 });
+
+for (const type of ["rsa", "rsa-pss", "dsa"]) {
+  for (const modulusLength of [2048, 3072]) {
+    Deno.test({
+      name: `generate ${type} key`,
+      fn() {
+        const { publicKey, privateKey } = generateKeyPairSync(type as any, {
+          modulusLength,
+        });
+
+        assertEquals(publicKey.type, "public");
+        assertEquals(privateKey.type, "private");
+      },
+    });
+
+    Deno.test({
+      name: `generate ${type} key async`,
+      async fn() {
+        const x = await generateKeyPairAsync(type as any, {
+          modulusLength,
+        });
+        const { publicKey, privateKey } = x;
+        assertEquals(publicKey.type, "public");
+        assertEquals(privateKey.type, "private");
+      },
+    });
+  }
+}
+
+for (const namedCurve of ["P-384", "P-256"]) {
+  Deno.test({
+    name: `generate ec key ${namedCurve}`,
+    fn() {
+      const { publicKey, privateKey } = generateKeyPairSync("ec", {
+        namedCurve,
+      });
+
+      assertEquals(publicKey.type, "public");
+      assertEquals(privateKey.type, "private");
+    },
+  });
+
+  Deno.test({
+    name: `generate ec key ${namedCurve} async`,
+    async fn() {
+      const { publicKey, privateKey } = await generateKeyPairAsync("ec", {
+        namedCurve,
+      });
+
+      assertEquals(publicKey.type, "public");
+      assertEquals(privateKey.type, "private");
+    },
+  });
+
+  Deno.test({
+    name: `generate ec key ${namedCurve} paramEncoding=explicit fails`,
+    fn() {
+      assertThrows(() => {
+        // @ts-ignore: @types/node is broken?
+        generateKeyPairSync("ec", {
+          namedCurve,
+          paramEncoding: "explicit",
+        });
+      });
+    },
+  });
+}
+
+for (
+  const groupName of ["modp5", "modp14", "modp15", "modp16", "modp17", "modp18"]
+) {
+  Deno.test({
+    name: `generate dh key ${groupName}`,
+    fn() {
+      // @ts-ignore: @types/node is broken?
+      const { publicKey, privateKey } = generateKeyPairSync("dh", {
+        group: groupName,
+      });
+
+      assertEquals(publicKey.type, "public");
+      assertEquals(privateKey.type, "private");
+    },
+  });
+
+  Deno.test({
+    name: `generate dh key ${groupName} async`,
+    async fn() {
+      // @ts-ignore: @types/node is broken?
+      const { publicKey, privateKey } = await generateKeyPairAsync("dh", {
+        group: groupName,
+      });
+
+      assertEquals(publicKey.type, "public");
+      assertEquals(privateKey.type, "private");
+    },
+  });
+}
+
+for (const primeLength of [1024, 2048, 4096]) {
+  Deno.test({
+    name: `generate dh key ${primeLength}`,
+    fn() {
+      // @ts-ignore: @types/node is broken?
+      const { publicKey, privateKey } = generateKeyPairSync("dh", {
+        primeLength,
+        generator: 2,
+      });
+
+      assertEquals(publicKey.type, "public");
+      assertEquals(privateKey.type, "private");
+    },
+  });
+
+  Deno.test({
+    name: `generate dh key ${primeLength} async`,
+    async fn() {
+      // @ts-ignore: @types/node is broken?
+      const { publicKey, privateKey } = await generateKeyPairAsync("dh", {
+        primeLength,
+        generator: 2,
+      });
+
+      assertEquals(publicKey.type, "public");
+      assertEquals(privateKey.type, "private");
+    },
+  });
+}
diff --git a/ext/node/Cargo.toml b/ext/node/Cargo.toml
index 5827b585aa..0d647e4f02 100644
--- a/ext/node/Cargo.toml
+++ b/ext/node/Cargo.toml
@@ -19,6 +19,7 @@ cbc.workspace = true
 data-encoding = "2.3.3"
 deno_core.workspace = true
 digest = { version = "0.10.5", features = ["core-api", "std"] }
+dsa = "0.6.1"
 ecb.workspace = true
 hex.workspace = true
 hkdf.workspace = true
@@ -29,6 +30,7 @@ libz-sys = { version = "1.1.8", features = ["static"] }
 md-5 = "0.10.5"
 md4 = "0.10.2"
 num-bigint.workspace = true
+num-bigint-dig = "0.8.2"
 num-integer = "0.1.45"
 num-traits = "0.2.14"
 once_cell.workspace = true
@@ -36,6 +38,7 @@ path-clean = "=0.1.0"
 pbkdf2 = "0.12.1"
 rand.workspace = true
 regex.workspace = true
+ring.workspace = true
 ripemd = "0.1.3"
 rsa.workspace = true
 scrypt = "0.11.0"
@@ -46,4 +49,6 @@ sha3 = "0.10.5"
 signature.workspace = true
 tokio.workspace = true
 typenum = "1.15.0"
+# https://github.com/dalek-cryptography/x25519-dalek/pull/89
+x25519-dalek = "2.0.0-pre.1"
 x509-parser = "0.15.0"
diff --git a/ext/node/crypto/dh.rs b/ext/node/crypto/dh.rs
new file mode 100644
index 0000000000..4da9a01bf8
--- /dev/null
+++ b/ext/node/crypto/dh.rs
@@ -0,0 +1,288 @@
+// Copyright 2018-2023 the Deno authors. All rights reserved. MIT license.
+
+use super::primes::Prime;
+use num_bigint_dig::BigUint;
+use num_bigint_dig::RandBigInt;
+use num_traits::FromPrimitive;
+
+pub struct PublicKey(BigUint);
+
+impl PublicKey {
+  pub fn into_vec(self) -> Vec<u8> {
+    self.0.to_bytes_be()
+  }
+}
+
+pub struct PrivateKey(BigUint);
+
+impl PrivateKey {
+  pub fn new(exponent_size: usize) -> Self {
+    let mut rng = rand::thread_rng();
+    let exponent = rng.gen_biguint(exponent_size);
+    Self(exponent)
+  }
+
+  /// Diffie-Hellman modular exponentiation.
+  /// s = g^x mod p
+  pub fn compute_public_key(
+    &self,
+    generator: &BigUint,
+    modulus: &BigUint,
+  ) -> PublicKey {
+    let public_key = generator.modpow(&self.0, modulus);
+    PublicKey(public_key)
+  }
+
+  pub fn into_vec(self) -> Vec<u8> {
+    self.0.to_bytes_be()
+  }
+}
+
+/// Classic DH
+pub struct DiffieHellman {
+  pub private_key: PrivateKey,
+  pub public_key: PublicKey,
+}
+
+impl DiffieHellman {
+  pub fn group<G>() -> Self
+  where
+    G: DiffieHellmanGroup,
+  {
+    let private_key = PrivateKey::new(G::EXPONENT_SIZE / 8);
+
+    let generator = BigUint::from_usize(G::GENERATOR).unwrap();
+    let modulus = BigUint::from_slice(G::MODULUS);
+
+    let public_key = private_key.compute_public_key(&generator, &modulus);
+
+    Self {
+      private_key,
+      public_key,
+    }
+  }
+
+  pub fn new(prime: Prime, generator: usize) -> Self {
+    let private_key = PrivateKey::new(32);
+
+    let generator = BigUint::from_usize(generator).unwrap();
+    let public_key = private_key.compute_public_key(&generator, &prime);
+
+    Self {
+      private_key,
+      public_key,
+    }
+  }
+}
+
+/// Well-known modp groups
+//
+/// More Modular Exponential (MODP) Diffie-Hellman groups for Internet Key Exchange (IKE)
+/// https://www.rfc-editor.org/rfc/rfc3526
+///
+/// Insecure groups `modp1` and `modp2` from https://www.rfc-editor.org/rfc/rfc2409.txt
+/// are deprecated in Node.js. We don't support them.
+pub trait DiffieHellmanGroup {
+  const GENERATOR: usize;
+  const MODULUS: &'static [u32];
+  /// Size of the exponent in bits
+  const EXPONENT_SIZE: usize;
+}
+
+/// 1536-bit MODP Group
+/// https://www.rfc-editor.org/rfc/rfc3526#section-2
+pub struct Modp1536;
+impl DiffieHellmanGroup for Modp1536 {
+  const GENERATOR: usize = 2;
+  const EXPONENT_SIZE: usize = 192;
+
+  const MODULUS: &'static [u32] = &[
+    0xFFFFFFFF, 0xFFFFFFFF, 0xC90FDAA2, 0x2168C234, 0xC4C6628B, 0x80DC1CD1,
+    0x29024E08, 0x8A67CC74, 0x020BBEA6, 0x3B139B22, 0x514A0879, 0x8E3404DD,
+    0xEF9519B3, 0xCD3A431B, 0x302B0A6D, 0xF25F1437, 0x4FE1356D, 0x6D51C245,
+    0xE485B576, 0x625E7EC6, 0xF44C42E9, 0xA637ED6B, 0x0BFF5CB6, 0xF406B7ED,
+    0xEE386BFB, 0x5A899FA5, 0xAE9F2411, 0x7C4B1FE6, 0x49286651, 0xECE45B3D,
+    0xC2007CB8, 0xA163BF05, 0x98DA4836, 0x1C55D39A, 0x69163FA8, 0xFD24CF5F,
+    0x83655D23, 0xDCA3AD96, 0x1C62F356, 0x208552BB, 0x9ED52907, 0x7096966D,
+    0x670C354E, 0x4ABC9804, 0xF1746C08, 0xCA237327, 0xFFFFFFFF, 0xFFFFFFFF,
+  ];
+}
+
+/// 2048-bit MODP Group
+/// https://www.rfc-editor.org/rfc/rfc3526#section-3
+pub struct Modp2048;
+impl DiffieHellmanGroup for Modp2048 {
+  const GENERATOR: usize = 2;
+  const EXPONENT_SIZE: usize = 256;
+
+  const MODULUS: &'static [u32] = &[
+    0xFFFFFFFF, 0xFFFFFFFF, 0xC90FDAA2, 0x2168C234, 0xC4C6628B, 0x80DC1CD1,
+    0x29024E08, 0x8A67CC74, 0x020BBEA6, 0x3B139B22, 0x514A0879, 0x8E3404DD,
+    0xEF9519B3, 0xCD3A431B, 0x302B0A6D, 0xF25F1437, 0x4FE1356D, 0x6D51C245,
+    0xE485B576, 0x625E7EC6, 0xF44C42E9, 0xA637ED6B, 0x0BFF5CB6, 0xF406B7ED,
+    0xEE386BFB, 0x5A899FA5, 0xAE9F2411, 0x7C4B1FE6, 0x49286651, 0xECE45B3D,
+    0xC2007CB8, 0xA163BF05, 0x98DA4836, 0x1C55D39A, 0x69163FA8, 0xFD24CF5F,
+    0x83655D23, 0xDCA3AD96, 0x1C62F356, 0x208552BB, 0x9ED52907, 0x7096966D,
+    0x670C354E, 0x4ABC9804, 0xF1746C08, 0xCA18217C, 0x32905E46, 0x2E36CE3B,
+    0xE39E772C, 0x180E8603, 0x9B2783A2, 0xEC07A28F, 0xB5C55DF0, 0x6F4C52C9,
+    0xDE2BCBF6, 0x95581718, 0x3995497C, 0xEA956AE5, 0x15D22618, 0x98FA0510,
+    0x15728E5A, 0x8AACAA68, 0xFFFFFFFF, 0xFFFFFFFF,
+  ];
+}
+
+/// 3072-bit MODP Group
+/// https://www.rfc-editor.org/rfc/rfc3526#section-4
+pub struct Modp3072;
+impl DiffieHellmanGroup for Modp3072 {
+  const GENERATOR: usize = 2;
+  const EXPONENT_SIZE: usize = 384;
+
+  const MODULUS: &'static [u32] = &[
+    0xFFFFFFFF, 0xFFFFFFFF, 0xC90FDAA2, 0x2168C234, 0xC4C6628B, 0x80DC1CD1,
+    0x29024E08, 0x8A67CC74, 0x020BBEA6, 0x3B139B22, 0x514A0879, 0x8E3404DD,
+    0xEF9519B3, 0xCD3A431B, 0x302B0A6D, 0xF25F1437, 0x4FE1356D, 0x6D51C245,
+    0xE485B576, 0x625E7EC6, 0xF44C42E9, 0xA637ED6B, 0x0BFF5CB6, 0xF406B7ED,
+    0xEE386BFB, 0x5A899FA5, 0xAE9F2411, 0x7C4B1FE6, 0x49286651, 0xECE45B3D,
+    0xC2007CB8, 0xA163BF05, 0x98DA4836, 0x1C55D39A, 0x69163FA8, 0xFD24CF5F,
+    0x83655D23, 0xDCA3AD96, 0x1C62F356, 0x208552BB, 0x9ED52907, 0x7096966D,
+    0x670C354E, 0x4ABC9804, 0xF1746C08, 0xCA18217C, 0x32905E46, 0x2E36CE3B,
+    0xE39E772C, 0x180E8603, 0x9B2783A2, 0xEC07A28F, 0xB5C55DF0, 0x6F4C52C9,
+    0xDE2BCBF6, 0x95581718, 0x3995497C, 0xEA956AE5, 0x15D22618, 0x98FA0510,
+    0x15728E5A, 0x8AAAC42D, 0xAD33170D, 0x04507A33, 0xA85521AB, 0xDF1CBA64,
+    0xECFB8504, 0x58DBEF0A, 0x8AEA7157, 0x5D060C7D, 0xB3970F85, 0xA6E1E4C7,
+    0xABF5AE8C, 0xDB0933D7, 0x1E8C94E0, 0x4A25619D, 0xCEE3D226, 0x1AD2EE6B,
+    0xF12FFA06, 0xD98A0864, 0xD8760273, 0x3EC86A64, 0x521F2B18, 0x177B200C,
+    0xBBE11757, 0x7A615D6C, 0x770988C0, 0xBAD946E2, 0x08E24FA0, 0x74E5AB31,
+    0x43DB5BFC, 0xE0FD108E, 0x4B82D120, 0xA93AD2CA, 0xFFFFFFFF, 0xFFFFFFFF,
+  ];
+}
+
+/// 4096-bit MODP Group
+/// https://www.rfc-editor.org/rfc/rfc3526#section-5
+pub struct Modp4096;
+impl DiffieHellmanGroup for Modp4096 {
+  const GENERATOR: usize = 2;
+  const EXPONENT_SIZE: usize = 512;
+
+  const MODULUS: &'static [u32] = &[
+    0xFFFFFFFF, 0xFFFFFFFF, 0xC90FDAA2, 0x2168C234, 0xC4C6628B, 0x80DC1CD1,
+    0x29024E08, 0x8A67CC74, 0x020BBEA6, 0x3B139B22, 0x514A0879, 0x8E3404DD,
+    0xEF9519B3, 0xCD3A431B, 0x302B0A6D, 0xF25F1437, 0x4FE1356D, 0x6D51C245,
+    0xE485B576, 0x625E7EC6, 0xF44C42E9, 0xA637ED6B, 0x0BFF5CB6, 0xF406B7ED,
+    0xEE386BFB, 0x5A899FA5, 0xAE9F2411, 0x7C4B1FE6, 0x49286651, 0xECE45B3D,
+    0xC2007CB8, 0xA163BF05, 0x98DA4836, 0x1C55D39A, 0x69163FA8, 0xFD24CF5F,
+    0x83655D23, 0xDCA3AD96, 0x1C62F356, 0x208552BB, 0x9ED52907, 0x7096966D,
+    0x670C354E, 0x4ABC9804, 0xF1746C08, 0xCA18217C, 0x32905E46, 0x2E36CE3B,
+    0xE39E772C, 0x180E8603, 0x9B2783A2, 0xEC07A28F, 0xB5C55DF0, 0x6F4C52C9,
+    0xDE2BCBF6, 0x95581718, 0x3995497C, 0xEA956AE5, 0x15D22618, 0x98FA0510,
+    0x15728E5A, 0x8AAAC42D, 0xAD33170D, 0x04507A33, 0xA85521AB, 0xDF1CBA64,
+    0xECFB8504, 0x58DBEF0A, 0x8AEA7157, 0x5D060C7D, 0xB3970F85, 0xA6E1E4C7,
+    0xABF5AE8C, 0xDB0933D7, 0x1E8C94E0, 0x4A25619D, 0xCEE3D226, 0x1AD2EE6B,
+    0xF12FFA06, 0xD98A0864, 0xD8760273, 0x3EC86A64, 0x521F2B18, 0x177B200C,
+    0xBBE11757, 0x7A615D6C, 0x770988C0, 0xBAD946E2, 0x08E24FA0, 0x74E5AB31,
+    0x43DB5BFC, 0xE0FD108E, 0x4B82D120, 0xA9210801, 0x1A723C12, 0xA787E6D7,
+    0x88719A10, 0xBDBA5B26, 0x99C32718, 0x6AF4E23C, 0x1A946834, 0xB6150BDA,
+    0x2583E9CA, 0x2AD44CE8, 0xDBBBC2DB, 0x04DE8EF9, 0x2E8EFC14, 0x1FBECAA6,
+    0x287C5947, 0x4E6BC05D, 0x99B2964F, 0xA090C3A2, 0x233BA186, 0x515BE7ED,
+    0x1F612970, 0xCEE2D7AF, 0xB81BDD76, 0x2170481C, 0xD0069127, 0xD5B05AA9,
+    0x93B4EA98, 0x8D8FDDC1, 0x86FFB7DC, 0x90A6C08F, 0x4DF435C9, 0x34063199,
+    0xFFFFFFFF, 0xFFFFFFFF,
+  ];
+}
+
+/// 6144-bit MODP Group
+/// https://www.rfc-editor.org/rfc/rfc3526#section-6
+pub struct Modp6144;
+impl DiffieHellmanGroup for Modp6144 {
+  const GENERATOR: usize = 2;
+  const EXPONENT_SIZE: usize = 768;
+
+  const MODULUS: &'static [u32] = &[
+    0xFFFFFFFF, 0xFFFFFFFF, 0xC90FDAA2, 0x2168C234, 0xC4C6628B, 0x80DC1CD1,
+    0x29024E08, 0x8A67CC74, 0x020BBEA6, 0x3B139B22, 0x514A0879, 0x8E3404DD,
+    0xEF9519B3, 0xCD3A431B, 0x302B0A6D, 0xF25F1437, 0x4FE1356D, 0x6D51C245,
+    0xE485B576, 0x625E7EC6, 0xF44C42E9, 0xA637ED6B, 0x0BFF5CB6, 0xF406B7ED,
+    0xEE386BFB, 0x5A899FA5, 0xAE9F2411, 0x7C4B1FE6, 0x49286651, 0xECE45B3D,
+    0xC2007CB8, 0xA163BF05, 0x98DA4836, 0x1C55D39A, 0x69163FA8, 0xFD24CF5F,
+    0x83655D23, 0xDCA3AD96, 0x1C62F356, 0x208552BB, 0x9ED52907, 0x7096966D,
+    0x670C354E, 0x4ABC9804, 0xF1746C08, 0xCA18217C, 0x32905E46, 0x2E36CE3B,
+    0xE39E772C, 0x180E8603, 0x9B2783A2, 0xEC07A28F, 0xB5C55DF0, 0x6F4C52C9,
+    0xDE2BCBF6, 0x95581718, 0x3995497C, 0xEA956AE5, 0x15D22618, 0x98FA0510,
+    0x15728E5A, 0x8AAAC42D, 0xAD33170D, 0x04507A33, 0xA85521AB, 0xDF1CBA64,
+    0xECFB8504, 0x58DBEF0A, 0x8AEA7157, 0x5D060C7D, 0xB3970F85, 0xA6E1E4C7,
+    0xABF5AE8C, 0xDB0933D7, 0x1E8C94E0, 0x4A25619D, 0xCEE3D226, 0x1AD2EE6B,
+    0xF12FFA06, 0xD98A0864, 0xD8760273, 0x3EC86A64, 0x521F2B18, 0x177B200C,
+    0xBBE11757, 0x7A615D6C, 0x770988C0, 0xBAD946E2, 0x08E24FA0, 0x74E5AB31,
+    0x43DB5BFC, 0xE0FD108E, 0x4B82D120, 0xA9210801, 0x1A723C12, 0xA787E6D7,
+    0x88719A10, 0xBDBA5B26, 0x99C32718, 0x6AF4E23C, 0x1A946834, 0xB6150BDA,
+    0x2583E9CA, 0x2AD44CE8, 0xDBBBC2DB, 0x04DE8EF9, 0x2E8EFC14, 0x1FBECAA6,
+    0x287C5947, 0x4E6BC05D, 0x99B2964F, 0xA090C3A2, 0x233BA186, 0x515BE7ED,
+    0x1F612970, 0xCEE2D7AF, 0xB81BDD76, 0x2170481C, 0xD0069127, 0xD5B05AA9,
+    0x93B4EA98, 0x8D8FDDC1, 0x86FFB7DC, 0x90A6C08F, 0x4DF435C9, 0x34028492,
+    0x36C3FAB4, 0xD27C7026, 0xC1D4DCB2, 0x602646DE, 0xC9751E76, 0x3DBA37BD,
+    0xF8FF9406, 0xAD9E530E, 0xE5DB382F, 0x413001AE, 0xB06A53ED, 0x9027D831,
+    0x179727B0, 0x865A8918, 0xDA3EDBEB, 0xCF9B14ED, 0x44CE6CBA, 0xCED4BB1B,
+    0xDB7F1447, 0xE6CC254B, 0x33205151, 0x2BD7AF42, 0x6FB8F401, 0x378CD2BF,
+    0x5983CA01, 0xC64B92EC, 0xF032EA15, 0xD1721D03, 0xF482D7CE, 0x6E74FEF6,
+    0xD55E702F, 0x46980C82, 0xB5A84031, 0x900B1C9E, 0x59E7C97F, 0xBEC7E8F3,
+    0x23A97A7E, 0x36CC88BE, 0x0F1D45B7, 0xFF585AC5, 0x4BD407B2, 0x2B4154AA,
+    0xCC8F6D7E, 0xBF48E1D8, 0x14CC5ED2, 0x0F8037E0, 0xA79715EE, 0xF29BE328,
+    0x06A1D58B, 0xB7C5DA76, 0xF550AA3D, 0x8A1FBFF0, 0xEB19CCB1, 0xA313D55C,
+    0xDA56C9EC, 0x2EF29632, 0x387FE8D7, 0x6E3C0468, 0x043E8F66, 0x3F4860EE,
+    0x12BF2D5B, 0x0B7474D6, 0xE694F91E, 0x6DCC4024, 0xFFFFFFFF, 0xFFFFFFFF,
+  ];
+}
+
+/// 8192-bit MODP Group
+/// https://www.rfc-editor.org/rfc/rfc3526#section-7
+pub struct Modp8192;
+impl DiffieHellmanGroup for Modp8192 {
+  const GENERATOR: usize = 2;
+  const EXPONENT_SIZE: usize = 1024;
+
+  const MODULUS: &'static [u32] = &[
+    0xFFFFFFFF, 0xFFFFFFFF, 0xC90FDAA2, 0x2168C234, 0xC4C6628B, 0x80DC1CD1,
+    0x29024E08, 0x8A67CC74, 0x020BBEA6, 0x3B139B22, 0x514A0879, 0x8E3404DD,
+    0xEF9519B3, 0xCD3A431B, 0x302B0A6D, 0xF25F1437, 0x4FE1356D, 0x6D51C245,
+    0xE485B576, 0x625E7EC6, 0xF44C42E9, 0xA637ED6B, 0x0BFF5CB6, 0xF406B7ED,
+    0xEE386BFB, 0x5A899FA5, 0xAE9F2411, 0x7C4B1FE6, 0x49286651, 0xECE45B3D,
+    0xC2007CB8, 0xA163BF05, 0x98DA4836, 0x1C55D39A, 0x69163FA8, 0xFD24CF5F,
+    0x83655D23, 0xDCA3AD96, 0x1C62F356, 0x208552BB, 0x9ED52907, 0x7096966D,
+    0x670C354E, 0x4ABC9804, 0xF1746C08, 0xCA18217C, 0x32905E46, 0x2E36CE3B,
+    0xE39E772C, 0x180E8603, 0x9B2783A2, 0xEC07A28F, 0xB5C55DF0, 0x6F4C52C9,
+    0xDE2BCBF6, 0x95581718, 0x3995497C, 0xEA956AE5, 0x15D22618, 0x98FA0510,
+    0x15728E5A, 0x8AAAC42D, 0xAD33170D, 0x04507A33, 0xA85521AB, 0xDF1CBA64,
+    0xECFB8504, 0x58DBEF0A, 0x8AEA7157, 0x5D060C7D, 0xB3970F85, 0xA6E1E4C7,
+    0xABF5AE8C, 0xDB0933D7, 0x1E8C94E0, 0x4A25619D, 0xCEE3D226, 0x1AD2EE6B,
+    0xF12FFA06, 0xD98A0864, 0xD8760273, 0x3EC86A64, 0x521F2B18, 0x177B200C,
+    0xBBE11757, 0x7A615D6C, 0x770988C0, 0xBAD946E2, 0x08E24FA0, 0x74E5AB31,
+    0x43DB5BFC, 0xE0FD108E, 0x4B82D120, 0xA9210801, 0x1A723C12, 0xA787E6D7,
+    0x88719A10, 0xBDBA5B26, 0x99C32718, 0x6AF4E23C, 0x1A946834, 0xB6150BDA,
+    0x2583E9CA, 0x2AD44CE8, 0xDBBBC2DB, 0x04DE8EF9, 0x2E8EFC14, 0x1FBECAA6,
+    0x287C5947, 0x4E6BC05D, 0x99B2964F, 0xA090C3A2, 0x233BA186, 0x515BE7ED,
+    0x1F612970, 0xCEE2D7AF, 0xB81BDD76, 0x2170481C, 0xD0069127, 0xD5B05AA9,
+    0x93B4EA98, 0x8D8FDDC1, 0x86FFB7DC, 0x90A6C08F, 0x4DF435C9, 0x34028492,
+    0x36C3FAB4, 0xD27C7026, 0xC1D4DCB2, 0x602646DE, 0xC9751E76, 0x3DBA37BD,
+    0xF8FF9406, 0xAD9E530E, 0xE5DB382F, 0x413001AE, 0xB06A53ED, 0x9027D831,
+    0x179727B0, 0x865A8918, 0xDA3EDBEB, 0xCF9B14ED, 0x44CE6CBA, 0xCED4BB1B,
+    0xDB7F1447, 0xE6CC254B, 0x33205151, 0x2BD7AF42, 0x6FB8F401, 0x378CD2BF,
+    0x5983CA01, 0xC64B92EC, 0xF032EA15, 0xD1721D03, 0xF482D7CE, 0x6E74FEF6,
+    0xD55E702F, 0x46980C82, 0xB5A84031, 0x900B1C9E, 0x59E7C97F, 0xBEC7E8F3,
+    0x23A97A7E, 0x36CC88BE, 0x0F1D45B7, 0xFF585AC5, 0x4BD407B2, 0x2B4154AA,
+    0xCC8F6D7E, 0xBF48E1D8, 0x14CC5ED2, 0x0F8037E0, 0xA79715EE, 0xF29BE328,
+    0x06A1D58B, 0xB7C5DA76, 0xF550AA3D, 0x8A1FBFF0, 0xEB19CCB1, 0xA313D55C,
+    0xDA56C9EC, 0x2EF29632, 0x387FE8D7, 0x6E3C0468, 0x043E8F66, 0x3F4860EE,
+    0x12BF2D5B, 0x0B7474D6, 0xE694F91E, 0x6DBE1159, 0x74A3926F, 0x12FEE5E4,
+    0x38777CB6, 0xA932DF8C, 0xD8BEC4D0, 0x73B931BA, 0x3BC832B6, 0x8D9DD300,
+    0x741FA7BF, 0x8AFC47ED, 0x2576F693, 0x6BA42466, 0x3AAB639C, 0x5AE4F568,
+    0x3423B474, 0x2BF1C978, 0x238F16CB, 0xE39D652D, 0xE3FDB8BE, 0xFC848AD9,
+    0x22222E04, 0xA4037C07, 0x13EB57A8, 0x1A23F0C7, 0x3473FC64, 0x6CEA306B,
+    0x4BCBC886, 0x2F8385DD, 0xFA9D4B7F, 0xA2C087E8, 0x79683303, 0xED5BDD3A,
+    0x062B3CF5, 0xB3A278A6, 0x6D2A13F8, 0x3F44F82D, 0xDF310EE0, 0x74AB6A36,
+    0x4597E899, 0xA0255DC1, 0x64F31CC5, 0x0846851D, 0xF9AB4819, 0x5DED7EA1,
+    0xB1D510BD, 0x7EE74D73, 0xFAF36BC3, 0x1ECFA268, 0x359046F4, 0xEB879F92,
+    0x4009438B, 0x481C6CD7, 0x889A002E, 0xD5EE382B, 0xC9190DA6, 0xFC026E47,
+    0x9558E447, 0x5677E9AA, 0x9E3050E2, 0x765694DF, 0xC81F56E8, 0x80B96E71,
+    0x60C980DD, 0x98EDD3DF, 0xFFFFFFFF, 0xFFFFFFFF,
+  ];
+}
diff --git a/ext/node/crypto/mod.rs b/ext/node/crypto/mod.rs
index 26392da4c0..d224b40f72 100644
--- a/ext/node/crypto/mod.rs
+++ b/ext/node/crypto/mod.rs
@@ -10,8 +10,10 @@ use deno_core::StringOrBuffer;
 use deno_core::ZeroCopyBuf;
 use hkdf::Hkdf;
 use num_bigint::BigInt;
+use num_traits::FromPrimitive;
 use rand::distributions::Distribution;
 use rand::distributions::Uniform;
+use rand::thread_rng;
 use rand::Rng;
 use std::future::Future;
 use std::rc::Rc;
@@ -24,6 +26,7 @@ use rsa::RsaPrivateKey;
 use rsa::RsaPublicKey;
 
 mod cipher;
+mod dh;
 mod digest;
 mod primes;
 pub mod x509;
@@ -534,6 +537,275 @@ pub async fn op_node_hkdf_async(
   .await?
 }
 
+use rsa::pkcs1::EncodeRsaPrivateKey;
+use rsa::pkcs1::EncodeRsaPublicKey;
+
+use self::primes::Prime;
+
+fn generate_rsa(
+  modulus_length: usize,
+  public_exponent: usize,
+) -> Result<(ZeroCopyBuf, ZeroCopyBuf), AnyError> {
+  let mut rng = rand::thread_rng();
+  let private_key = RsaPrivateKey::new_with_exp(
+    &mut rng,
+    modulus_length,
+    &rsa::BigUint::from_usize(public_exponent).unwrap(),
+  )?;
+  let public_key = private_key.to_public_key();
+  let private_key_der = private_key.to_pkcs1_der()?.as_bytes().to_vec();
+  let public_key_der = public_key.to_pkcs1_der()?.to_vec();
+
+  Ok((private_key_der.into(), public_key_der.into()))
+}
+
+#[op]
+pub fn op_node_generate_rsa(
+  modulus_length: usize,
+  public_exponent: usize,
+) -> Result<(ZeroCopyBuf, ZeroCopyBuf), AnyError> {
+  generate_rsa(modulus_length, public_exponent)
+}
+
+#[op]
+pub async fn op_node_generate_rsa_async(
+  modulus_length: usize,
+  public_exponent: usize,
+) -> Result<(ZeroCopyBuf, ZeroCopyBuf), AnyError> {
+  tokio::task::spawn_blocking(move || {
+    generate_rsa(modulus_length, public_exponent)
+  })
+  .await?
+}
+
+fn dsa_generate(
+  modulus_length: usize,
+  divisor_length: usize,
+) -> Result<(ZeroCopyBuf, ZeroCopyBuf), AnyError> {
+  let mut rng = rand::thread_rng();
+  use dsa::pkcs8::EncodePrivateKey;
+  use dsa::pkcs8::EncodePublicKey;
+  use dsa::Components;
+  use dsa::KeySize;
+  use dsa::SigningKey;
+
+  let key_size = match (modulus_length, divisor_length) {
+    #[allow(deprecated)]
+    (1024, 160) => KeySize::DSA_1024_160,
+    (2048, 224) => KeySize::DSA_2048_224,
+    (2048, 256) => KeySize::DSA_2048_256,
+    (3072, 256) => KeySize::DSA_3072_256,
+    _ => return Err(type_error("Invalid modulus_length or divisor_length")),
+  };
+  let components = Components::generate(&mut rng, key_size);
+  let signing_key = SigningKey::generate(&mut rng, components);
+  let verifying_key = signing_key.verifying_key();
+
+  Ok((
+    signing_key
+      .to_pkcs8_der()
+      .map_err(|_| type_error("Not valid pkcs8"))?
+      .as_bytes()
+      .to_vec()
+      .into(),
+    verifying_key
+      .to_public_key_der()
+      .map_err(|_| type_error("Not valid spki"))?
+      .to_vec()
+      .into(),
+  ))
+}
+
+#[op]
+pub fn op_node_dsa_generate(
+  modulus_length: usize,
+  divisor_length: usize,
+) -> Result<(ZeroCopyBuf, ZeroCopyBuf), AnyError> {
+  dsa_generate(modulus_length, divisor_length)
+}
+
+#[op]
+pub async fn op_node_dsa_generate_async(
+  modulus_length: usize,
+  divisor_length: usize,
+) -> Result<(ZeroCopyBuf, ZeroCopyBuf), AnyError> {
+  tokio::task::spawn_blocking(move || {
+    dsa_generate(modulus_length, divisor_length)
+  })
+  .await?
+}
+
+fn ec_generate(
+  named_curve: &str,
+) -> Result<(ZeroCopyBuf, ZeroCopyBuf), AnyError> {
+  use ring::signature::EcdsaKeyPair;
+  use ring::signature::KeyPair;
+
+  let curve = match named_curve {
+    "P-256" => &ring::signature::ECDSA_P256_SHA256_FIXED_SIGNING,
+    "P-384" => &ring::signature::ECDSA_P384_SHA384_FIXED_SIGNING,
+    _ => return Err(type_error("Unsupported named curve")),
+  };
+
+  let rng = ring::rand::SystemRandom::new();
+
+  let pkcs8 = EcdsaKeyPair::generate_pkcs8(curve, &rng)
+    .map_err(|_| type_error("Failed to generate EC key"))?;
+
+  let public_key = EcdsaKeyPair::from_pkcs8(curve, pkcs8.as_ref())
+    .map_err(|_| type_error("Failed to generate EC key"))?
+    .public_key()
+    .as_ref()
+    .to_vec();
+  Ok((pkcs8.as_ref().to_vec().into(), public_key.into()))
+}
+
+#[op]
+pub fn op_node_ec_generate(
+  named_curve: &str,
+) -> Result<(ZeroCopyBuf, ZeroCopyBuf), AnyError> {
+  ec_generate(named_curve)
+}
+
+#[op]
+pub async fn op_node_ec_generate_async(
+  named_curve: String,
+) -> Result<(ZeroCopyBuf, ZeroCopyBuf), AnyError> {
+  tokio::task::spawn_blocking(move || ec_generate(&named_curve)).await?
+}
+
+fn ed25519_generate() -> Result<(ZeroCopyBuf, ZeroCopyBuf), AnyError> {
+  use ring::signature::Ed25519KeyPair;
+  use ring::signature::KeyPair;
+
+  let mut rng = thread_rng();
+  let mut seed = vec![0u8; 32];
+  rng.fill(seed.as_mut_slice());
+
+  let pair = Ed25519KeyPair::from_seed_unchecked(&seed)
+    .map_err(|_| type_error("Failed to generate Ed25519 key"))?;
+
+  let public_key = pair.public_key().as_ref().to_vec();
+  Ok((seed.into(), public_key.into()))
+}
+
+#[op]
+pub fn op_node_ed25519_generate() -> Result<(ZeroCopyBuf, ZeroCopyBuf), AnyError>
+{
+  ed25519_generate()
+}
+
+#[op]
+pub async fn op_node_ed25519_generate_async(
+) -> Result<(ZeroCopyBuf, ZeroCopyBuf), AnyError> {
+  tokio::task::spawn_blocking(ed25519_generate).await?
+}
+
+fn x25519_generate() -> Result<(ZeroCopyBuf, ZeroCopyBuf), AnyError> {
+  // u-coordinate of the base point.
+  const X25519_BASEPOINT_BYTES: [u8; 32] = [
+    9, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0,
+    0, 0, 0, 0, 0, 0, 0,
+  ];
+
+  let mut pkey = [0; 32];
+
+  let mut rng = thread_rng();
+  rng.fill(pkey.as_mut_slice());
+
+  let pkey_copy = pkey.to_vec();
+  // https://www.rfc-editor.org/rfc/rfc7748#section-6.1
+  // pubkey = x25519(a, 9) which is constant-time Montgomery ladder.
+  //   https://eprint.iacr.org/2014/140.pdf page 4
+  //   https://eprint.iacr.org/2017/212.pdf algorithm 8
+  // pubkey is in LE order.
+  let pubkey = x25519_dalek::x25519(pkey, X25519_BASEPOINT_BYTES);
+
+  Ok((pkey_copy.into(), pubkey.to_vec().into()))
+}
+
+#[op]
+pub fn op_node_x25519_generate() -> Result<(ZeroCopyBuf, ZeroCopyBuf), AnyError>
+{
+  x25519_generate()
+}
+
+#[op]
+pub async fn op_node_x25519_generate_async(
+) -> Result<(ZeroCopyBuf, ZeroCopyBuf), AnyError> {
+  tokio::task::spawn_blocking(x25519_generate).await?
+}
+
+fn dh_generate_group(
+  group_name: &str,
+) -> Result<(ZeroCopyBuf, ZeroCopyBuf), AnyError> {
+  let dh = match group_name {
+    "modp5" => dh::DiffieHellman::group::<dh::Modp1536>(),
+    "modp14" => dh::DiffieHellman::group::<dh::Modp2048>(),
+    "modp15" => dh::DiffieHellman::group::<dh::Modp3072>(),
+    "modp16" => dh::DiffieHellman::group::<dh::Modp4096>(),
+    "modp17" => dh::DiffieHellman::group::<dh::Modp6144>(),
+    "modp18" => dh::DiffieHellman::group::<dh::Modp8192>(),
+    _ => return Err(type_error("Unsupported group name")),
+  };
+
+  Ok((
+    dh.private_key.into_vec().into(),
+    dh.public_key.into_vec().into(),
+  ))
+}
+
+#[op]
+pub fn op_node_dh_generate_group(
+  group_name: &str,
+) -> Result<(ZeroCopyBuf, ZeroCopyBuf), AnyError> {
+  dh_generate_group(group_name)
+}
+
+#[op]
+pub async fn op_node_dh_generate_group_async(
+  group_name: String,
+) -> Result<(ZeroCopyBuf, ZeroCopyBuf), AnyError> {
+  tokio::task::spawn_blocking(move || dh_generate_group(&group_name)).await?
+}
+
+fn dh_generate(
+  prime: Option<&[u8]>,
+  prime_len: usize,
+  generator: usize,
+) -> Result<(ZeroCopyBuf, ZeroCopyBuf), AnyError> {
+  let prime = prime
+    .map(|p| p.into())
+    .unwrap_or_else(|| Prime::generate(prime_len));
+  let dh = dh::DiffieHellman::new(prime, generator);
+
+  Ok((
+    dh.private_key.into_vec().into(),
+    dh.public_key.into_vec().into(),
+  ))
+}
+
+#[op]
+pub fn op_node_dh_generate(
+  prime: Option<&[u8]>,
+  prime_len: usize,
+  generator: usize,
+) -> Result<(ZeroCopyBuf, ZeroCopyBuf), AnyError> {
+  dh_generate(prime, prime_len, generator)
+}
+
+#[op]
+pub async fn op_node_dh_generate_async(
+  prime: Option<ZeroCopyBuf>,
+  prime_len: usize,
+  generator: usize,
+) -> Result<(ZeroCopyBuf, ZeroCopyBuf), AnyError> {
+  tokio::task::spawn_blocking(move || {
+    dh_generate(prime.as_deref(), prime_len, generator)
+  })
+  .await?
+}
+
 #[op]
 pub fn op_node_random_int(min: i32, max: i32) -> Result<i32, AnyError> {
   let mut rng = rand::thread_rng();
diff --git a/ext/node/crypto/primes.rs b/ext/node/crypto/primes.rs
index f438d87259..d03398f024 100644
--- a/ext/node/crypto/primes.rs
+++ b/ext/node/crypto/primes.rs
@@ -1,10 +1,35 @@
 // Copyright 2018-2023 the Deno authors. All rights reserved. MIT license.
 
 use num_bigint::BigInt;
+use num_bigint_dig::RandPrime;
 use num_integer::Integer;
 use num_traits::One;
 use num_traits::Zero;
 use rand::Rng;
+use std::ops::Deref;
+
+pub struct Prime(num_bigint_dig::BigUint);
+
+impl Prime {
+  pub fn generate(n: usize) -> Self {
+    let mut rng = rand::thread_rng();
+    Self(rng.gen_prime(n))
+  }
+}
+
+impl From<&[u8]> for Prime {
+  fn from(value: &[u8]) -> Self {
+    Self(num_bigint_dig::BigUint::from_bytes_be(value))
+  }
+}
+
+impl Deref for Prime {
+  type Target = num_bigint_dig::BigUint;
+
+  fn deref(&self) -> &Self::Target {
+    &self.0
+  }
+}
 
 struct Witness {
   pow: BigInt,
diff --git a/ext/node/lib.rs b/ext/node/lib.rs
index d363c444af..64a2e083ab 100644
--- a/ext/node/lib.rs
+++ b/ext/node/lib.rs
@@ -194,6 +194,20 @@ deno_core::extension!(deno_node,
     crypto::op_node_generate_secret,
     crypto::op_node_generate_secret_async,
     crypto::op_node_sign,
+    crypto::op_node_generate_rsa,
+    crypto::op_node_generate_rsa_async,
+    crypto::op_node_dsa_generate,
+    crypto::op_node_dsa_generate_async,
+    crypto::op_node_ec_generate,
+    crypto::op_node_ec_generate_async,
+    crypto::op_node_ed25519_generate,
+    crypto::op_node_ed25519_generate_async,
+    crypto::op_node_x25519_generate,
+    crypto::op_node_x25519_generate_async,
+    crypto::op_node_dh_generate_group,
+    crypto::op_node_dh_generate_group_async,
+    crypto::op_node_dh_generate,
+    crypto::op_node_dh_generate_async,
     crypto::op_node_verify,
     crypto::op_node_random_int,
     crypto::op_node_scrypt_sync,
diff --git a/ext/node/polyfills/internal/crypto/keygen.ts b/ext/node/polyfills/internal/crypto/keygen.ts
index b490cedd79..cdc616db6d 100644
--- a/ext/node/polyfills/internal/crypto/keygen.ts
+++ b/ext/node/polyfills/internal/crypto/keygen.ts
@@ -1,3 +1,5 @@
+// deno-lint-ignore-file no-explicit-any
+
 // Copyright 2018-2023 the Deno authors. All rights reserved. MIT license.
 // Copyright Joyent, Inc. and Node.js contributors. All rights reserved. MIT license.
 
@@ -8,13 +10,20 @@ import {
   setOwnedKey,
 } from "ext:deno_node/internal/crypto/keys.ts";
 import { notImplemented } from "ext:deno_node/_utils.ts";
-import { ERR_INVALID_ARG_VALUE } from "ext:deno_node/internal/errors.ts";
 import {
+  ERR_INCOMPATIBLE_OPTION_PAIR,
+  ERR_INVALID_ARG_VALUE,
+  ERR_MISSING_OPTION,
+} from "ext:deno_node/internal/errors.ts";
+import {
+  validateBuffer,
   validateFunction,
+  validateInt32,
   validateInteger,
   validateObject,
   validateOneOf,
   validateString,
+  validateUint32,
 } from "ext:deno_node/internal/validators.mjs";
 import { Buffer } from "ext:deno_node/buffer.ts";
 import { KeyFormat, KeyType } from "ext:deno_node/internal/crypto/types.ts";
@@ -529,17 +538,34 @@ export function generateKeyPair(
   ) => void,
 ): void;
 export function generateKeyPair(
-  _type: KeyType,
-  _options: unknown,
-  _callback: (
+  type: KeyType,
+  options: unknown,
+  callback: (
     err: Error | null,
-    // deno-lint-ignore no-explicit-any
     publicKey: any,
-    // deno-lint-ignore no-explicit-any
     privateKey: any,
   ) => void,
 ) {
-  notImplemented("crypto.generateKeyPair");
+  createJob(kAsync, type, options).then(([privateKey, publicKey]) => {
+    privateKey = new KeyObject("private", setOwnedKey(privateKey));
+    publicKey = new KeyObject("public", setOwnedKey(publicKey));
+
+    if (typeof options === "object" && options !== null) {
+      const { publicKeyEncoding, privateKeyEncoding } = options as any;
+
+      if (publicKeyEncoding) {
+        publicKey = publicKey.export(publicKeyEncoding);
+      }
+
+      if (privateKeyEncoding) {
+        privateKey = privateKey.export(privateKeyEncoding);
+      }
+    }
+
+    callback(null, publicKey, privateKey);
+  }).catch((err) => {
+    callback(err, null, null);
+  });
 }
 
 export interface KeyPairKeyObjectResult {
@@ -716,12 +742,241 @@ export function generateKeyPairSync(
   options?: X448KeyPairKeyObjectOptions,
 ): KeyPairKeyObjectResult;
 export function generateKeyPairSync(
-  _type: KeyType,
-  _options: unknown,
+  type: KeyType,
+  options: unknown,
 ):
   | KeyPairKeyObjectResult
   | KeyPairSyncResult<string | Buffer, string | Buffer> {
-  notImplemented("crypto.generateKeyPairSync");
+  let [privateKey, publicKey] = createJob(kSync, type, options);
+
+  privateKey = new KeyObject("private", setOwnedKey(privateKey));
+  publicKey = new KeyObject("public", setOwnedKey(publicKey));
+
+  if (typeof options === "object" && options !== null) {
+    const { publicKeyEncoding, privateKeyEncoding } = options as any;
+
+    if (publicKeyEncoding) {
+      publicKey = publicKey.export(publicKeyEncoding);
+    }
+
+    if (privateKeyEncoding) {
+      privateKey = privateKey.export(privateKeyEncoding);
+    }
+  }
+
+  return { publicKey, privateKey };
+}
+
+const kSync = 0;
+const kAsync = 1;
+
+function createJob(mode, type, options) {
+  validateString(type, "type");
+
+  if (options !== undefined) {
+    validateObject(options, "options");
+  }
+
+  switch (type) {
+    case "rsa":
+    case "rsa-pss": {
+      validateObject(options, "options");
+      const { modulusLength } = options;
+      validateUint32(modulusLength, "options.modulusLength");
+
+      let { publicExponent } = options;
+      if (publicExponent == null) {
+        publicExponent = 0x10001;
+      } else {
+        validateUint32(publicExponent, "options.publicExponent");
+      }
+
+      if (type === "rsa") {
+        if (mode === kSync) {
+          return ops.op_node_generate_rsa(
+            modulusLength,
+            publicExponent,
+          );
+        } else {
+          return core.opAsync(
+            "op_node_generate_rsa_async",
+            modulusLength,
+            publicExponent,
+          );
+        }
+      }
+
+      const {
+        hash,
+        mgf1Hash,
+        hashAlgorithm,
+        mgf1HashAlgorithm,
+        saltLength,
+      } = options;
+
+      if (saltLength !== undefined) {
+        validateInt32(saltLength, "options.saltLength", 0);
+      }
+      if (hashAlgorithm !== undefined) {
+        validateString(hashAlgorithm, "options.hashAlgorithm");
+      }
+      if (mgf1HashAlgorithm !== undefined) {
+        validateString(mgf1HashAlgorithm, "options.mgf1HashAlgorithm");
+      }
+      if (hash !== undefined) {
+        process.emitWarning(
+          '"options.hash" is deprecated, ' +
+            'use "options.hashAlgorithm" instead.',
+          "DeprecationWarning",
+          "DEP0154",
+        );
+        validateString(hash, "options.hash");
+        if (hashAlgorithm && hash !== hashAlgorithm) {
+          throw new ERR_INVALID_ARG_VALUE("options.hash", hash);
+        }
+      }
+      if (mgf1Hash !== undefined) {
+        process.emitWarning(
+          '"options.mgf1Hash" is deprecated, ' +
+            'use "options.mgf1HashAlgorithm" instead.',
+          "DeprecationWarning",
+          "DEP0154",
+        );
+        validateString(mgf1Hash, "options.mgf1Hash");
+        if (mgf1HashAlgorithm && mgf1Hash !== mgf1HashAlgorithm) {
+          throw new ERR_INVALID_ARG_VALUE("options.mgf1Hash", mgf1Hash);
+        }
+      }
+
+      if (mode === kSync) {
+        return ops.op_node_generate_rsa(
+          modulusLength,
+          publicExponent,
+        );
+      } else {
+        return core.opAsync(
+          "op_node_generate_rsa_async",
+          modulusLength,
+          publicExponent,
+        );
+      }
+    }
+    case "dsa": {
+      validateObject(options, "options");
+      const { modulusLength } = options;
+      validateUint32(modulusLength, "options.modulusLength");
+
+      let { divisorLength } = options;
+      if (divisorLength == null) {
+        divisorLength = 256;
+      } else {
+        validateInt32(divisorLength, "options.divisorLength", 0);
+      }
+
+      if (mode === kSync) {
+        return ops.op_node_dsa_generate(modulusLength, divisorLength);
+      }
+      return core.opAsync(
+        "op_node_dsa_generate_async",
+        modulusLength,
+        divisorLength,
+      );
+    }
+    case "ec": {
+      validateObject(options, "options");
+      const { namedCurve } = options;
+      validateString(namedCurve, "options.namedCurve");
+      const { paramEncoding } = options;
+      if (paramEncoding == null || paramEncoding === "named") {
+        // pass.
+      } else if (paramEncoding === "explicit") {
+        // TODO(@littledivy): Explicit param encoding is very rarely used, and not supported by the ring crate.
+        throw new TypeError("Explicit encoding is not supported");
+      } else {
+        throw new ERR_INVALID_ARG_VALUE("options.paramEncoding", paramEncoding);
+      }
+
+      if (mode === kSync) {
+        return ops.op_node_ec_generate(namedCurve);
+      } else {
+        return core.opAsync("op_node_ec_generate_async", namedCurve);
+      }
+    }
+    case "ed25519": {
+      if (mode === kSync) {
+        return ops.op_node_ed25519_generate();
+      }
+      return core.opAsync("op_node_ed25519_generate_async");
+    }
+    case "x25519": {
+      if (mode === kSync) {
+        return ops.op_node_x25519_generate();
+      }
+      return core.opAsync("op_node_x25519_generate_async");
+    }
+    case "ed448":
+    case "x448": {
+      notImplemented(type);
+      break;
+    }
+    case "dh": {
+      validateObject(options, "options");
+      const { group, primeLength, prime, generator } = options;
+      if (group != null) {
+        if (prime != null) {
+          throw new ERR_INCOMPATIBLE_OPTION_PAIR("group", "prime");
+        }
+        if (primeLength != null) {
+          throw new ERR_INCOMPATIBLE_OPTION_PAIR("group", "primeLength");
+        }
+        if (generator != null) {
+          throw new ERR_INCOMPATIBLE_OPTION_PAIR("group", "generator");
+        }
+
+        validateString(group, "options.group");
+
+        if (mode === kSync) {
+          return ops.op_node_dh_generate_group(group);
+        } else {
+          return core.opAsync("op_node_dh_generate_group_async", group);
+        }
+      }
+
+      if (prime != null) {
+        if (primeLength != null) {
+          throw new ERR_INCOMPATIBLE_OPTION_PAIR("prime", "primeLength");
+        }
+
+        validateBuffer(prime, "options.prime");
+      } else if (primeLength != null) {
+        validateInt32(primeLength, "options.primeLength", 0);
+      } else {
+        throw new ERR_MISSING_OPTION(
+          "At least one of the group, prime, or primeLength options",
+        );
+      }
+
+      if (generator != null) {
+        validateInt32(generator, "options.generator", 0);
+      }
+
+      const g = generator == null ? 2 : generator;
+
+      if (mode === kSync) {
+        return ops.op_node_dh_generate(prime, primeLength ?? 0, g);
+      } else {
+        return core.opAsync(
+          "op_node_dh_generate_async",
+          prime,
+          primeLength ?? 0,
+          g,
+        );
+      }
+    }
+    default:
+      // Fall through
+  }
+  throw new ERR_INVALID_ARG_VALUE("type", type, "must be a supported key type");
 }
 
 export default {