diff --git a/ape_aws/accounts.py b/ape_aws/accounts.py
index 4e8d4ac..2c707ec 100644
--- a/ape_aws/accounts.py
+++ b/ape_aws/accounts.py
@@ -70,14 +70,23 @@ def address(self) -> AddressType:
             keccak(self.public_key[-64:])[-20:].hex().lower()
         )
 
-    def sign_raw_msghash(self, msghash: HexBytes) -> Optional[bytes]:
+    def sign_raw_msghash(self, msghash: HexBytes) -> Optional[MessageSignature]:
+        if len(msghash) != 32:
+            return None
+
+        if signature := self.sign_raw_hash(msghash):
+            return MessageSignature(**_convert_der_to_rsv(signature, 27))
+
+        return None
+
+    def sign_raw_hash(self, msghash: HexBytes) -> Optional[bytes]:
         response = self.kms_client.sign(
             KeyId=self.key_id,
             Message=msghash,
             MessageType='DIGEST',
             SigningAlgorithm='ECDSA_SHA_256',
         )
-        return response['Signature']
+        return response.get('Signature')
 
     def sign_message(
         self, msg: Any, **signer_options
@@ -91,14 +100,12 @@ def sign_message(
                 message = encode_defunct(text=msg)
         if isinstance(msg, bytes):
             message = encode_defunct(primitive=msg)
-        signature = self.sign_raw_msghash(_hash_eip191_message(message))
-        r, s = _convert_der_to_rsv(signature)
-        for v in [signature[0] + 27, signature[0] + 28]:
-            if self.check_signature(
-                msg,
-                message_signature := MessageSignature(v=v, r=r, s=s),
-            ):
-                return message_signature
+        msg_sig = self.sign_raw_msghash(_hash_eip191_message(message))
+        # Note: check here until we figure out v
+        if self.check_signature(msg, msg_sig):
+            return msg_sig
+        else:
+            return MessageSignature(v=msg_sig.v + 1, r=msg_sig.r, s=msg_sig.s)
 
     def sign_transaction(self, txn: TransactionAPI, **signer_options) -> Optional[TransactionAPI]:
         """
@@ -120,11 +127,9 @@ def sign_transaction(self, txn: TransactionAPI, **signer_options) -> Optional[Tr
                 data=txn.data
             )
         ).hash()
-        signature = self.sign_raw_msghash(unsigned_txn)
-        r, s = _convert_der_to_rsv(signature)
-        for v in [signature[0] + 27, signature[0] + 28]:
-            if self.check_signature(
-                unsigned_txn,
-                message_signature := MessageSignature(v=v, r=r, s=s),
-            ):
-                return message_signature
+        msg_sig = self.sign_raw_msghash(unsigned_txn)
+        breakpoint()
+        if self.check_signature(unsigned_txn, msg_sig):
+            return msg_sig
+        else:
+            return MessageSignature(v=msg_sig.v + 1, r=msg_sig.r, s=msg_sig.s)
diff --git a/ape_aws/utils.py b/ape_aws/utils.py
index 176a6cf..a4290d2 100644
--- a/ape_aws/utils.py
+++ b/ape_aws/utils.py
@@ -30,13 +30,16 @@ def create_signable_message(msg):
     return encode_defunct(text=msg)
 
 
-def _convert_der_to_rsv(signature: bytes) -> dict:
+def _convert_der_to_rsv(
+    signature: bytes, v_adjustment_factor: int = 0
+) -> dict:
     r, s = ecdsa.util.sigdecode_der(signature, ecdsa.SECP256k1.order)
     if s > SECP256_K1_N / 2:
         s = SECP256_K1_N - s
     r = r.to_bytes(32, byteorder='big')
     s = s.to_bytes(32, byteorder='big')
-    return r, s
+    v = signature[0] + v_adjustment_factor
+    return dict(v=v, r=r, s=s)
 
 
 class AliasResponse(BaseModel):