diff --git a/src_py/_backend.py b/src_py/_backend.py
index 1109e62..9b1ff49 100644
--- a/src_py/_backend.py
+++ b/src_py/_backend.py
@@ -8,6 +8,7 @@
 _CAPI_MODULE: Any | None = None
 _PYBIND_MODULE: Any | None = None
 _PYBIND_IMPORT_ATTEMPTED = False
+_PYBIND_IMPORT_ERROR: ImportError | None = None
 
 
 def _import_pybind_module() -> Any:
@@ -32,12 +33,35 @@ def get_capi_module() -> Any:
 
 
 def get_pybind_module() -> Any | None:
-    global _PYBIND_MODULE, _PYBIND_IMPORT_ATTEMPTED
+    global _PYBIND_MODULE, _PYBIND_IMPORT_ATTEMPTED, _PYBIND_IMPORT_ERROR
     if _PYBIND_IMPORT_ATTEMPTED:
         return _PYBIND_MODULE
     _PYBIND_IMPORT_ATTEMPTED = True
     try:
         _PYBIND_MODULE = _import_pybind_module()
-    except ImportError:
+    except ImportError as exc:
         _PYBIND_MODULE = None
+        _PYBIND_IMPORT_ERROR = exc
     return _PYBIND_MODULE
+
+
+def missing_capi_library_message() -> str:
+    """
+    Explain why neither backend could load.
+
+    The C API library is the fallback when the bundled ``_lbug`` extension fails to import, so a missing C API
+    library usually hides the real failure. Include that failure, such as a missing OpenSSL 3 runtime.
+    """
+    msg = (
+        "Could not find lbug C API shared library. "
+        "Set LBUG_C_API_LIB_PATH or download a shared lib (e.g. run "
+        "LBUG_LIB_KIND=shared bash scripts/download_lbug.sh)."
+    )
+    if _PYBIND_IMPORT_ERROR is None:
+        return msg
+    msg += f" The bundled _lbug extension, which is tried first, failed to load: {_PYBIND_IMPORT_ERROR}"
+    if "libssl" in str(_PYBIND_IMPORT_ERROR) or "libcrypto" in str(
+        _PYBIND_IMPORT_ERROR
+    ):
+        msg += " Ladybug needs an OpenSSL 3 runtime; on macOS, install it with `brew install openssl@3`."
+    return msg
diff --git a/src_py/_lbug_capi.py b/src_py/_lbug_capi.py
index 332249d..95806a6 100644
--- a/src_py/_lbug_capi.py
+++ b/src_py/_lbug_capi.py
@@ -178,12 +178,9 @@ def _resolve_library_path() -> str:
     if found:
         return found
 
-    msg = (
-        "Could not find lbug C API shared library. "
-        "Set LBUG_C_API_LIB_PATH or download a shared lib (e.g. run "
-        "LBUG_LIB_KIND=shared bash scripts/download_lbug.sh)."
-    )
-    raise RuntimeError(msg)
+    from ._backend import missing_capi_library_message
+
+    raise RuntimeError(missing_capi_library_message())
 
 
 _dlopen_mode = getattr(ctypes, "RTLD_GLOBAL", 0) | getattr(ctypes, "RTLD_NOW", 0)
diff --git a/test/test_backend_errors.py b/test/test_backend_errors.py
new file mode 100644
index 0000000..1934051
--- /dev/null
+++ b/test/test_backend_errors.py
@@ -0,0 +1,34 @@
+from __future__ import annotations
+
+import ladybug._backend as backend
+
+
+def test_missing_capi_message_without_pybind_error(monkeypatch) -> None:
+    monkeypatch.setattr(backend, "_PYBIND_IMPORT_ERROR", None)
+    msg = backend.missing_capi_library_message()
+    assert msg.startswith("Could not find lbug C API shared library.")
+    assert "_lbug extension" not in msg
+
+
+def test_missing_capi_message_reports_pybind_error(monkeypatch) -> None:
+    error = ImportError(
+        "dlopen(_lbug.cpython-312-darwin.so, 0x0002): Library not loaded: /opt/homebrew/opt/openssl@3/lib/libssl.3.dylib"
+    )
+    monkeypatch.setattr(backend, "_PYBIND_IMPORT_ERROR", error)
+    msg = backend.missing_capi_library_message()
+    assert "Library not loaded: /opt/homebrew/opt/openssl@3/lib/libssl.3.dylib" in msg
+    assert "brew install openssl@3" in msg
+
+
+def test_failed_pybind_import_is_recorded(monkeypatch) -> None:
+    error = ImportError("Library not loaded: libcrypto.3.dylib")
+
+    def fail() -> None:
+        raise error
+
+    monkeypatch.setattr(backend, "_PYBIND_IMPORT_ATTEMPTED", False)
+    monkeypatch.setattr(backend, "_PYBIND_MODULE", None)
+    monkeypatch.setattr(backend, "_PYBIND_IMPORT_ERROR", None)
+    monkeypatch.setattr(backend, "_import_pybind_module", fail)
+    assert backend.get_pybind_module() is None
+    assert "libcrypto.3.dylib" in str(backend._PYBIND_IMPORT_ERROR)