diff --git a/CHANGELOG.md b/CHANGELOG.md
index e20cafa43..1a0706cca 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -8,6 +8,13 @@ All versions prior to 0.9.0 are untracked.
 
 ## [Unreleased]
 
+### Changed
+
+* **BREAKING API CHANGE**: `sigstore.sign.SigningResult` has been removed
+  ([#862](https://github.com/sigstore/sigstore-python/pull/862))
+* **BREAKING API CHANGE**: The `Signer.sign(...)` API now returns a `Bundle`,
+  instead of a `SigningResult` ([#862](https://github.com/sigstore/sigstore-python/pull/862))
+
 ## [2.1.0]
 
 ### Added
diff --git a/pyproject.toml b/pyproject.toml
index f4232915e..c5225d816 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -60,9 +60,7 @@ lint = [
   # and let Dependabot periodically perform this update.
   "ruff < 0.1.14",
   "types-requests",
-  # TODO(ww): Re-enable once dependency on types-cryptography is dropped.
-  # See: https://github.com/python/typeshed/issues/8699
-  # "types-pyOpenSSL",
+  "types-pyOpenSSL",
 ]
 doc = ["pdoc"]
 dev = ["build", "bump >= 1.3.2", "sigstore[doc,test,lint]"]
diff --git a/sigstore/_cli.py b/sigstore/_cli.py
index 0b08c09e6..da9714cba 100644
--- a/sigstore/_cli.py
+++ b/sigstore/_cli.py
@@ -41,7 +41,7 @@
     RekorKeyring,
 )
 from sigstore._internal.trustroot import TrustedRoot
-from sigstore._utils import PEMCert
+from sigstore._utils import PEMCert, cert_der_to_pem
 from sigstore.errors import Error
 from sigstore.oidc import (
     DEFAULT_OAUTH_ISSUER_URL,
@@ -698,10 +698,12 @@ def _sign(args: argparse.Namespace) -> None:
                     raise exp_certificate
 
             print("Using ephemeral certificate:")
-            print(result.cert_pem)
+            cert = result.verification_material.x509_certificate_chain.certificates[0]
+            cert_pem = cert_der_to_pem(cert.raw_bytes)
+            print(cert_pem)
 
             print(
-                f"Transparency log entry created at index: {result.log_entry.log_index}"
+                f"Transparency log entry created at index: {result.verification_material.tlog_entries[0].log_index}"
             )
 
             sig_output: TextIO
@@ -710,18 +712,19 @@ def _sign(args: argparse.Namespace) -> None:
             else:
                 sig_output = sys.stdout
 
-            print(result.b64_signature, file=sig_output)
+            signature = base64.b64encode(result.message_signature.signature).decode()
+            print(signature, file=sig_output)
             if outputs["sig"] is not None:
                 print(f"Signature written to {outputs['sig']}")
 
             if outputs["cert"] is not None:
                 with outputs["cert"].open(mode="w") as io:
-                    print(result.cert_pem, file=io)
+                    print(cert_pem, file=io)
                 print(f"Certificate written to {outputs['cert']}")
 
             if outputs["bundle"] is not None:
                 with outputs["bundle"].open(mode="w") as io:
-                    print(result.to_bundle().to_json(), file=io)
+                    print(result.to_json(), file=io)
                 print(f"Sigstore bundle written to {outputs['bundle']}")
 
 
diff --git a/sigstore/_utils.py b/sigstore/_utils.py
index e6487c68f..0e4463566 100644
--- a/sigstore/_utils.py
+++ b/sigstore/_utils.py
@@ -25,7 +25,12 @@
 
 from cryptography.hazmat.primitives import serialization
 from cryptography.hazmat.primitives.asymmetric import ec, rsa
-from cryptography.x509 import Certificate, ExtensionNotFound, Version
+from cryptography.x509 import (
+    Certificate,
+    ExtensionNotFound,
+    Version,
+    load_der_x509_certificate,
+)
 from cryptography.x509.oid import ExtendedKeyUsageOID, ExtensionOID
 
 from sigstore.errors import Error
@@ -126,6 +131,19 @@ def base64_encode_pem_cert(cert: Certificate) -> B64Str:
     )
 
 
+def cert_der_to_pem(der: bytes) -> str:
+    """
+    Converts a DER-encoded X.509 certificate into its PEM encoding.
+
+    Returns a string containing a PEM-encoded X.509 certificate.
+    """
+
+    # NOTE: Technically we don't have to round-trip like this, since
+    # the DER-to-PEM transformation is entirely mechanical.
+    cert = load_der_x509_certificate(der)
+    return cert.public_bytes(serialization.Encoding.PEM).decode()
+
+
 def key_id(key: PublicKey) -> KeyID:
     """
     Returns an RFC 6962-style "key ID" for the given public key.
diff --git a/sigstore/sign.py b/sigstore/sign.py
index b37ae98a6..e03d6fad9 100644
--- a/sigstore/sign.py
+++ b/sigstore/sign.py
@@ -51,7 +51,6 @@
 from cryptography.hazmat.primitives.asymmetric import ec
 from cryptography.hazmat.primitives.asymmetric.utils import Prehashed
 from cryptography.x509.oid import NameOID
-from pydantic import BaseModel
 from sigstore_protobuf_specs.dev.sigstore.bundle.v1 import (
     Bundle,
     VerificationMaterial,
@@ -175,7 +174,7 @@ def _signing_cert(
     def sign(
         self,
         input_: IO[bytes],
-    ) -> SigningResult:
+    ) -> Bundle:
         """Public API for signing blobs"""
         input_digest = sha256_streaming(input_)
         private_key = self._private_key
@@ -233,7 +232,7 @@ def sign(
 
         logger.debug(f"Transparency log entry created with index: {entry.log_index}")
 
-        return SigningResult(
+        return _make_bundle(
             input_digest=HexStr(input_digest.hex()),
             cert_pem=PEMCert(
                 cert.public_bytes(encoding=serialization.Encoding.PEM).decode()
@@ -308,90 +307,60 @@ def signer(
         yield Signer(identity_token, self, cache)
 
 
-class SigningResult(BaseModel):
+def _make_bundle(
+    input_digest: HexStr, cert_pem: PEMCert, b64_signature: B64Str, log_entry: LogEntry
+) -> Bundle:
     """
-    Represents the artifacts of a signing operation.
+    Convert the raw results of a Sigstore signing operation into a Sigstore bundle.
     """
 
-    input_digest: HexStr
-    """
-    The hex-encoded SHA256 digest of the input that was signed for.
-    """
-
-    cert_pem: PEMCert
-    """
-    The PEM-encoded public half of the certificate used for signing.
-    """
-
-    b64_signature: B64Str
-    """
-    The base64-encoded signature.
-    """
-
-    log_entry: LogEntry
-    """
-    A record of the Rekor log entry for the signing operation.
-    """
-
-    def to_bundle(self) -> Bundle:
-        """
-        Creates a Sigstore bundle (as defined by Sigstore's protobuf specs)
-        from this `SigningResult`.
-        """
-
-        # NOTE: We explicitly only include the leaf certificate in the bundle's "chain"
-        # here: the specs explicitly forbid the inclusion of the root certificate,
-        # and discourage inclusion of any intermediates (since they're in the root of
-        # trust already).
-        cert = x509.load_pem_x509_certificate(self.cert_pem.encode())
-        cert_der = cert.public_bytes(encoding=serialization.Encoding.DER)
-        chain = X509CertificateChain(certificates=[X509Certificate(raw_bytes=cert_der)])
-
-        inclusion_proof: InclusionProof | None = None
-        if self.log_entry.inclusion_proof is not None:
-            inclusion_proof = InclusionProof(
-                log_index=self.log_entry.inclusion_proof.log_index,
-                root_hash=bytes.fromhex(self.log_entry.inclusion_proof.root_hash),
-                tree_size=self.log_entry.inclusion_proof.tree_size,
-                hashes=[
-                    bytes.fromhex(h) for h in self.log_entry.inclusion_proof.hashes
-                ],
-                checkpoint=Checkpoint(
-                    envelope=self.log_entry.inclusion_proof.checkpoint
-                ),
-            )
-
-        tlog_entry = TransparencyLogEntry(
-            log_index=self.log_entry.log_index,
-            log_id=LogId(key_id=bytes.fromhex(self.log_entry.log_id)),
-            kind_version=KindVersion(kind="hashedrekord", version="0.0.1"),
-            integrated_time=self.log_entry.integrated_time,
-            inclusion_promise=InclusionPromise(
-                signed_entry_timestamp=base64.b64decode(
-                    self.log_entry.inclusion_promise
-                )
-            )
-            if self.log_entry.inclusion_promise
-            else None,
-            inclusion_proof=inclusion_proof,
-            canonicalized_body=base64.b64decode(self.log_entry.body),
+    # NOTE: We explicitly only include the leaf certificate in the bundle's "chain"
+    # here: the specs explicitly forbid the inclusion of the root certificate,
+    # and discourage inclusion of any intermediates (since they're in the root of
+    # trust already).
+    cert = x509.load_pem_x509_certificate(cert_pem.encode())
+    cert_der = cert.public_bytes(encoding=serialization.Encoding.DER)
+    chain = X509CertificateChain(certificates=[X509Certificate(raw_bytes=cert_der)])
+
+    inclusion_proof: InclusionProof | None = None
+    if log_entry.inclusion_proof is not None:
+        inclusion_proof = InclusionProof(
+            log_index=log_entry.inclusion_proof.log_index,
+            root_hash=bytes.fromhex(log_entry.inclusion_proof.root_hash),
+            tree_size=log_entry.inclusion_proof.tree_size,
+            hashes=[bytes.fromhex(h) for h in log_entry.inclusion_proof.hashes],
+            checkpoint=Checkpoint(envelope=log_entry.inclusion_proof.checkpoint),
         )
 
-        material = VerificationMaterial(
-            x509_certificate_chain=chain,
-            tlog_entries=[tlog_entry],
+    tlog_entry = TransparencyLogEntry(
+        log_index=log_entry.log_index,
+        log_id=LogId(key_id=bytes.fromhex(log_entry.log_id)),
+        kind_version=KindVersion(kind="hashedrekord", version="0.0.1"),
+        integrated_time=log_entry.integrated_time,
+        inclusion_promise=InclusionPromise(
+            signed_entry_timestamp=base64.b64decode(log_entry.inclusion_promise)
         )
-
-        bundle = Bundle(
-            media_type="application/vnd.dev.sigstore.bundle+json;version=0.2",
-            verification_material=material,
-            message_signature=MessageSignature(
-                message_digest=HashOutput(
-                    algorithm=HashAlgorithm.SHA2_256,
-                    digest=bytes.fromhex(self.input_digest),
-                ),
-                signature=base64.b64decode(self.b64_signature),
+        if log_entry.inclusion_promise
+        else None,
+        inclusion_proof=inclusion_proof,
+        canonicalized_body=base64.b64decode(log_entry.body),
+    )
+
+    material = VerificationMaterial(
+        x509_certificate_chain=chain,
+        tlog_entries=[tlog_entry],
+    )
+
+    bundle = Bundle(
+        media_type="application/vnd.dev.sigstore.bundle+json;version=0.2",
+        verification_material=material,
+        message_signature=MessageSignature(
+            message_digest=HashOutput(
+                algorithm=HashAlgorithm.SHA2_256,
+                digest=bytes.fromhex(input_digest),
             ),
-        )
+            signature=base64.b64decode(b64_signature),
+        ),
+    )
 
-        return bundle
+    return bundle
diff --git a/sigstore/verify/verifier.py b/sigstore/verify/verifier.py
index 3477fab38..999e40b27 100644
--- a/sigstore/verify/verifier.py
+++ b/sigstore/verify/verifier.py
@@ -29,7 +29,7 @@
 from cryptography.hazmat.primitives.asymmetric.utils import Prehashed
 from cryptography.x509 import Certificate, ExtendedKeyUsage, KeyUsage
 from cryptography.x509.oid import ExtendedKeyUsageOID
-from OpenSSL.crypto import (  # type: ignore[import-untyped]
+from OpenSSL.crypto import (
     X509,
     X509Store,
     X509StoreContext,
diff --git a/test/unit/conftest.py b/test/unit/conftest.py
index fa71dd476..304167337 100644
--- a/test/unit/conftest.py
+++ b/test/unit/conftest.py
@@ -12,6 +12,8 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 
+from __future__ import annotations
+
 import base64
 import os
 import re
@@ -238,7 +240,7 @@ def tuf_dirs(monkeypatch, tmp_path):
     ],
     ids=["production", "staging"],
 )
-def id_config(request):
+def id_config(request) -> tuple[SigningContext, IdentityToken]:
     env, signer = request.param
     # Detect env variable for local interactive tests.
     token = os.getenv(f"SIGSTORE_IDENTITY_TOKEN_{env}")
diff --git a/test/unit/test_sign.py b/test/unit/test_sign.py
index a030a495e..ac6370ec7 100644
--- a/test/unit/test_sign.py
+++ b/test/unit/test_sign.py
@@ -12,6 +12,7 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 
+import base64
 import io
 import secrets
 
@@ -45,14 +46,13 @@ def test_sign_rekor_entry_consistent(id_config):
 
     payload = io.BytesIO(secrets.token_bytes(32))
     with ctx.signer(identity) as signer:
-        expected_entry = signer.sign(payload).log_entry
+        expected_entry = signer.sign(payload).verification_material.tlog_entries[0]
 
     actual_entry = ctx._rekor.log.entries.get(log_index=expected_entry.log_index)
 
-    assert expected_entry.uuid == actual_entry.uuid
-    assert expected_entry.body == actual_entry.body
+    assert expected_entry.canonicalized_body == base64.b64decode(actual_entry.body)
     assert expected_entry.integrated_time == actual_entry.integrated_time
-    assert expected_entry.log_id == actual_entry.log_id
+    assert expected_entry.log_id.key_id == bytes.fromhex(actual_entry.log_id)
     assert expected_entry.log_index == actual_entry.log_index
 
 
@@ -109,11 +109,10 @@ def test_identity_proof_claim_lookup(id_config, monkeypatch):
     payload = io.BytesIO(secrets.token_bytes(32))
 
     with ctx.signer(identity) as signer:
-        expected_entry = signer.sign(payload).log_entry
+        expected_entry = signer.sign(payload).verification_material.tlog_entries[0]
     actual_entry = ctx._rekor.log.entries.get(log_index=expected_entry.log_index)
 
-    assert expected_entry.uuid == actual_entry.uuid
-    assert expected_entry.body == actual_entry.body
+    assert expected_entry.canonicalized_body == base64.b64decode(actual_entry.body)
     assert expected_entry.integrated_time == actual_entry.integrated_time
-    assert expected_entry.log_id == actual_entry.log_id
+    assert expected_entry.log_id.key_id == bytes.fromhex(actual_entry.log_id)
     assert expected_entry.log_index == actual_entry.log_index