diff --git a/ra-tls/src/kdf.rs b/ra-tls/src/kdf.rs
index a6e07a32..3b4e3b4d 100644
--- a/ra-tls/src/kdf.rs
+++ b/ra-tls/src/kdf.rs
@@ -12,6 +12,49 @@ use ring::{
 };
 use rustls_pki_types::PrivateKeyDer;
 
+// PKCS#8 PrivateKeyInfo template for a P-256 key generated by p256/pkcs8 0.10,
+// without the EC public key. This prefix is stable because all lengths and
+// algorithm identifiers are constant for prime256v1.
+//
+// Structure:
+// PrivateKeyInfo ::= SEQUENCE {
+//   version               INTEGER (0),
+//   privateKeyAlgorithm   AlgorithmIdentifier {
+//     id-ecPublicKey, prime256v1
+//   },
+//   privateKey            OCTET STRING (ECPrivateKey)
+// }
+//
+// ECPrivateKey ::= SEQUENCE {
+//   version       INTEGER (1),
+//   privateKey    OCTET STRING (32 bytes),
+//   publicKey   [1] BIT STRING OPTIONAL
+// }
+//
+// The remaining suffix encodes the [1] publicKey BIT STRING header; the
+// actual SEC1-encoded uncompressed point (65 bytes) is appended after it.
+const P256_PKCS8_PREFIX: [u8; 36] = [
+    0x30, 0x81, 0x87, // SEQUENCE, len 0x87
+    0x02, 0x01, 0x00, // version = 0
+    0x30, 0x13, // SEQUENCE (AlgorithmIdentifier)
+    0x06, 0x07, 0x2a, 0x86, 0x48, 0xce, 0x3d, 0x02, 0x01, // id-ecPublicKey
+    0x06, 0x08, 0x2a, 0x86, 0x48, 0xce, 0x3d, 0x03, 0x01, 0x07, // prime256v1
+    0x04, 0x6d, // OCTET STRING, len 0x6d (ECPrivateKey)
+    0x30, 0x6b, // SEQUENCE (ECPrivateKey), len 0x6b
+    0x02, 0x01, 0x01, // version = 1
+    0x04, 0x20, // OCTET STRING, len 32 (private key)
+];
+
+// Context-specific [1] publicKey BIT STRING wrapper; the 65-byte SEC1
+// uncompressed point (0x04 || X || Y) is appended after this header.
+const P256_PKCS8_PUBLIC_KEY_PREFIX: [u8; 5] = [
+    0xa1, 0x44, // [1] constructed, len 0x44
+    0x03, 0x42, // BIT STRING, len 0x42
+    0x00, // number of unused bits
+];
+
+const P256_PKCS8_TOTAL_LEN: usize = 138;
+
 struct AnySizeKey(usize);
 impl KeyType for AnySizeKey {
     fn len(&self) -> usize {
@@ -66,9 +109,65 @@ fn sha256(data: &[u8]) -> [u8; 32] {
 }
 
 /// Derives a X25519 secret from a given key pair.
+///
+/// Historically this was implemented as:
+///   1. derive a P-256 key pair from `from` using HKDF
+///   2. hash `rcgen::KeyPair::serialized_der()` with SHA-256
+///
+/// That made the result sensitive to library-level changes in PKCS#8
+/// encoding. To avoid this, we now:
+///   - derive the same P-256 scalar as before
+///   - encode it using a fixed, Dstack-defined PKCS#8 layout
+///   - hash that encoding with SHA-256
 pub fn derive_dh_secret(from: &KeyPair, context_data: &[&[u8]]) -> Result<[u8; 32]> {
-    let key_pair = derive_p256_key_pair(from, context_data)?;
-    let derived_secret = sha256(key_pair.serialized_der());
+    use p256::elliptic_curve::sec1::ToEncodedPoint;
+
+    // 1. Decode the root CA key from rcgen::KeyPair into a P-256 scalar.
+    let der_bytes = from.serialized_der();
+    let sk =
+        p256::SecretKey::from_pkcs8_der(der_bytes).context("failed to decode root secret key")?;
+    let sk_bytes = sk.as_scalar_primitive().to_bytes();
+
+    // 2. Derive the same 32-byte scalar as before using HKDF.
+    let derived_sk_bytes = derive_key(sk_bytes.as_slice(), context_data, 32)
+        .or(Err(anyhow!("failed to derive key")))?;
+    let derived_sk_bytes: [u8; 32] = derived_sk_bytes
+        .as_slice()
+        .try_into()
+        .map_err(|_| anyhow!("unexpected length for derived key"))?;
+
+    // 3. Compute the corresponding P-256 public key (uncompressed SEC1).
+    let derived_sk = p256::SecretKey::from_slice(&derived_sk_bytes)
+        .context("failed to decode derived secret key")?;
+    let public_key = derived_sk.public_key();
+    let encoded_point = public_key.to_encoded_point(false);
+    let public_key_bytes = encoded_point.as_bytes(); // 0x04 || X || Y (65 bytes)
+
+    // 4. Build a fixed PKCS#8 PrivateKeyInfo encoding matching the previous
+    //    rcgen/pkcs8 output for prime256v1 keys.
+    anyhow::ensure!(
+        public_key_bytes.len() == 65,
+        "unexpected P-256 public key length"
+    );
+
+    let mut pkcs8 = [0u8; P256_PKCS8_TOTAL_LEN];
+    // Prefix up to the private key OCTET STRING contents.
+    pkcs8[..P256_PKCS8_PREFIX.len()].copy_from_slice(&P256_PKCS8_PREFIX);
+
+    // 32-byte private key.
+    let mut offset = P256_PKCS8_PREFIX.len();
+    pkcs8[offset..offset + 32].copy_from_slice(&derived_sk_bytes);
+    offset += 32;
+
+    // [1] BIT STRING public key header.
+    pkcs8[offset..offset + P256_PKCS8_PUBLIC_KEY_PREFIX.len()]
+        .copy_from_slice(&P256_PKCS8_PUBLIC_KEY_PREFIX);
+    offset += P256_PKCS8_PUBLIC_KEY_PREFIX.len();
+
+    // SEC1-encoded uncompressed public key bytes.
+    pkcs8[offset..offset + public_key_bytes.len()].copy_from_slice(public_key_bytes);
+
+    let derived_secret = sha256(&pkcs8);
     Ok(derived_secret)
 }
 
@@ -95,4 +194,19 @@ mod tests {
         let key = KeyPair::generate_for(&PKCS_ECDSA_P256_SHA256).unwrap();
         let _derived_key = derive_p256_key_pair(&key, &[b"context one"]).unwrap();
     }
+
+    #[test]
+    fn test_derive_dh_secret_compatible_with_previous_encoding() {
+        let root_key = KeyPair::generate_for(&PKCS_ECDSA_P256_SHA256).unwrap();
+        let context = [b"context one".as_ref(), b"context two".as_ref()];
+
+        // New implementation under test.
+        let new_secret = derive_dh_secret(&root_key, &context).unwrap();
+
+        // Previous behaviour: derive P-256 key pair with HKDF, then hash PKCS#8 DER.
+        let old_key_pair = derive_p256_key_pair(&root_key, &context).unwrap();
+        let old_secret = sha256(old_key_pair.serialized_der());
+
+        assert_eq!(new_secret, old_secret);
+    }
 }