diff --git a/.gitignore b/.gitignore
index a1122a4..9361233 100644
--- a/.gitignore
+++ b/.gitignore
@@ -8,3 +8,5 @@ __pycache__
 coverage.xml
 
 dist
+
+*.pyc
diff --git a/passlib/handlers/bcrypt.py b/passlib/handlers/bcrypt.py
index 121a12c..8c225a3 100644
--- a/passlib/handlers/bcrypt.py
+++ b/passlib/handlers/bcrypt.py
@@ -152,6 +152,7 @@ class _BcryptCommon(  # type: ignore[misc]
     _lacks_2b_support = False
     _fallback_ident = IDENT_2A
     _require_valid_utf8_bytes = False
+    _backend_raises_on_truncate = False
 
     @classmethod
     def from_string(cls, hash):
@@ -370,21 +371,20 @@ def detect_wrap_bug(ident):
             # Secret which will trip the wraparound bug, if present
             secret = (b"0123456789" * 26)[:255]
 
-            # Python bcrypt >= 5.0.0 will raise an exception on passwords greater than 72 characters,
-            # whereas earlier versions without the wraparound bug silently truncated the input to 72
-            # characters. See if the exception is generated.
-            try:
+            if not mixin_cls._backend_raises_on_truncate:
+                # Backend accepts more than 72 characters, test for the wraparound bug
                 bug_hash = (
                     ident.encode("ascii")
                     + b"04$R1lJ2gkNaoPGdafE.H.16.nVyh2niHsGJhayOHLMiXlI45o8/DU.6"
                 )
 
-                # If we get here, the backend auto-truncates, test for wraparound bug
                 if verify(secret, bug_hash):
                     return True
-            except ValueError:
-                # Backend explicitly will not auto-truncate, truncate the password to 72 characters
-                secret = secret[:72]
+            else:
+                # Backend won't accept more than 72 characters, truncate the secret
+                #
+                # n.b. this should preclude the wraparound bug existing anyway
+                secret = secret[:mixin_cls.truncate_size]
 
             # Check to make sure that the backend still hashes correctly; if not, we're in a failure case
             # not related to the original wraparound bug or bcrypt >= 5.0.0 input length restriction.
@@ -620,11 +620,15 @@ def _load_backend_mixin(mixin_cls, name, dryrun):
             return False
         try:
             version = metadata.version("bcrypt")
+
+            if int(version.split(".")[0]) >= 5:
+                mixin_cls._backend_raises_on_truncate = True
         except Exception:
             logger.warning("(trapped) error reading bcrypt version", exc_info=True)
             version = "<unknown>"
 
         logger.debug("detected 'bcrypt' backend, version %r", version)
+
         return mixin_cls._finalize_backend_mixin(name, dryrun)
 
     # # TODO: would like to implementing verify() directly,
@@ -654,6 +658,10 @@ def _calc_checksum(self, secret):
         config = self._get_config(ident)
         if isinstance(config, str):
             config = config.encode("ascii")
+
+        if self._backend_raises_on_truncate:
+            secret = secret[:72]
+
         hash = _bcrypt.hashpw(secret, config)
         assert isinstance(hash, bytes)
         if not hash.startswith(config) or len(hash) != len(config) + 31:
diff --git a/tests/test_handlers_bcrypt.py b/tests/test_handlers_bcrypt.py
index b49c1fb..a9134e8 100644
--- a/tests/test_handlers_bcrypt.py
+++ b/tests/test_handlers_bcrypt.py
@@ -220,9 +220,9 @@ def check_bcrypt(secret, hash):
                 hash = IDENT_2B + hash[4:]
             hash = to_bytes(hash)
             try:
-                return bcrypt.hashpw(secret, hash) == hash
-            except ValueError:
-                raise ValueError(f"bcrypt rejected hash: {hash!r} (secret={secret!r})")
+                return bcrypt.hashpw(secret[:72], hash) == hash
+            except ValueError as e:
+                raise ValueError(f"bcrypt rejected hash: {hash!r} (secret={secret!r}) with message: {str(e)}")
 
         return check_bcrypt