diff --git a/src/specify_cli/bundler/services/installer.py b/src/specify_cli/bundler/services/installer.py
index 58e220638d..78c1c90dd0 100644
--- a/src/specify_cli/bundler/services/installer.py
+++ b/src/specify_cli/bundler/services/installer.py
@@ -11,6 +11,7 @@
 """
 from __future__ import annotations
 
+import logging
 from dataclasses import dataclass, field
 from pathlib import Path
 from typing import Protocol
@@ -250,8 +251,10 @@ def _rollback(
     installer: PrimitiveInstaller,
     done: list[ComponentRef],
 ) -> None:
+    logger = logging.getLogger(__name__)
     for component in reversed(done):
         try:
             installer.remove(project_root, component)
         except Exception:  # noqa: BLE001 - best-effort rollback
+            logger.debug("rollback failed for %s", component, exc_info=True)
             continue
diff --git a/tests/unit/test_bundler_primitives.py b/tests/unit/test_bundler_primitives.py
index dc39106b50..ea03bc3889 100644
--- a/tests/unit/test_bundler_primitives.py
+++ b/tests/unit/test_bundler_primitives.py
@@ -334,3 +334,24 @@ def _plan(manifest):
         effective_integration=None,
         components=components,
     )
+
+
+class TestRollbackLoggingRegression:
+    """Regression: _rollback() must log errors, not silently swallow them."""
+
+    def test_rollback_logs_exception_on_remove_failure(self, caplog, tmp_path):
+        """When installer.remove() fails, _rollback() must log the error."""
+        import logging
+        from unittest.mock import MagicMock
+        from specify_cli.bundler.services.installer import _rollback
+        from specify_cli.bundler.models.manifest import ComponentRef
+
+        installer = MagicMock()
+        installer.remove.side_effect = RuntimeError("simulated remove failure")
+        done = [ComponentRef(kind="extensions", id="test-ext")]
+
+        with caplog.at_level(logging.DEBUG):
+            _rollback(tmp_path, installer, done)
+
+        assert any("rollback failed" in record.message for record in caplog.records)
+        assert any("test-ext" in record.message for record in caplog.records)