diff --git a/jbi/jira/client.py b/jbi/jira/client.py
index 9c1155fe..9ca88faa 100644
--- a/jbi/jira/client.py
+++ b/jbi/jira/client.py
@@ -78,6 +78,23 @@ def raise_for_status(self, *args, **kwargs):
     create_issue = instrumented_method(Jira.create_issue)
     get_project = instrumented_method(Jira.get_project)
 
+    @instrumented_method
+    def get_issue_transitions_with_fields(self, issue_key: str) -> list[dict]:
+        """Get available transitions for an issue with field metadata.
+
+        This uses expand=transitions.fields to get information about which
+        fields are available on each transition screen.
+
+        Args:
+            issue_key: The issue key (e.g., "SYNC-5055")
+
+        Returns:
+            List of transition objects with field metadata
+        """
+        url = f"rest/api/2/issue/{issue_key}/transitions"
+        response = self.get(url, params={"expand": "transitions.fields"})
+        return response.get("transitions", []) if response else []
+
     @instrumented_method
     def paginated_projects(
         self,
diff --git a/jbi/jira/service.py b/jbi/jira/service.py
index 1bf3a55d..0602db5b 100644
--- a/jbi/jira/service.py
+++ b/jbi/jira/service.py
@@ -307,9 +307,24 @@ def update_issue_status(self, context: ActionContext, jira_status: str):
 
         kwargs: dict[str, Any] = {}
         if jira_status == "Cancelled":
-            kwargs["fields"] = {
-                "resolution": {"name": "Invalid"},
-            }
+            # Check if resolution field is available on the transition screen
+            transitions = self.client.get_issue_transitions_with_fields(issue_key)
+            target_transition = next(
+                (t for t in transitions if t.get("to", {}).get("name") == jira_status),
+                None,
+            )
+
+            if target_transition and "resolution" in target_transition.get("fields", {}):
+                kwargs["fields"] = {
+                    "resolution": {"name": "Invalid"},
+                }
+            else:
+                logger.info(
+                    "Resolution field not available on transition screen for %s, skipping",
+                    issue_key,
+                    extra=context.model_dump(),
+                )
+
             kwargs["update"] = {
                 "comment": [{"add": {"body": "Issue was cancelled."}}],
             }
diff --git a/tests/unit/jira/test_service.py b/tests/unit/jira/test_service.py
index 19ede6fe..9dfd8f57 100644
--- a/tests/unit/jira/test_service.py
+++ b/tests/unit/jira/test_service.py
@@ -180,6 +180,25 @@ def test_update_issue_status_adds_comment_and_resolution_when_cancelled(
     context = action_context_factory(jira__issue="JBI-234")
     url = f"{settings.jira_base_url}rest/api/2/issue/JBI-234/transitions"
 
+    # Mock GET transitions with expand=transitions.fields (for checking resolution availability)
+    mocked_responses.add(
+        responses.GET,
+        url,
+        match=[
+            responses.matchers.query_param_matcher({"expand": "transitions.fields"})
+        ],
+        json={
+            "transitions": [
+                {
+                    "name": "foo",
+                    "id": 42,
+                    "to": {"name": "Cancelled"},
+                    "fields": {"resolution": {"required": True}},
+                }
+            ]
+        },
+    )
+    # Mock GET transitions (for set_issue_status to find transition ID)
     mocked_responses.add(
         responses.GET,
         url,