diff --git a/jbi/jira/client.py b/jbi/jira/client.py
index 34d66efe..863c2231 100644
--- a/jbi/jira/client.py
+++ b/jbi/jira/client.py
@@ -1,3 +1,4 @@
+import json
 import logging
 from typing import Collection, Iterable, Optional
 
@@ -54,6 +55,7 @@ def raise_for_status(self, *args, **kwargs):
         except requests.HTTPError as exc:
             request = exc.request
             response = exc.response
+            assert response is not None, f"HTTPError {exc} has no attached response"
             atlassian_logger.error(
                 "HTTP: %s %s -> %s %s",
                 request.method,
@@ -62,6 +64,18 @@ def raise_for_status(self, *args, **kwargs):
                 response.reason,
                 extra={"body": response.text},
             )
+            if str(exc) == "":
+                # Some Jira errors are raised as `HTTPError('')`.
+                # We are trying to turn them into insightful errors here.
+                try:
+                    content = exc.response.json()
+                    errors = content.get("errors", {})
+                    response_details = ",".join(f"{k}: {v}" for k, v in errors.items())
+                except json.JSONDecodeError:
+                    response_details = exc.response.text
+                # Set the exception message so that its str version contains details.
+                msg = f"HTTP {exc.response.status_code}: {response_details}"
+                exc.args = (msg,) + exc.args[1:]
             raise
 
     get_server_info = instrumented_method(Jira.get_server_info)
diff --git a/tests/unit/jira/test_queue.py b/tests/unit/jira/test_queue.py
index 9b1737ec..148f7d32 100644
--- a/tests/unit/jira/test_queue.py
+++ b/tests/unit/jira/test_queue.py
@@ -178,7 +178,7 @@ async def test_backend_get_invalid_json(backend: QueueBackend, queue_item_factor
     with pytest.raises(QueueItemRetrievalError):
         await anext(items)
 
-        
+
 async def test_get_missing_timezone(backend: QueueBackend, queue_item_factory):
     item = queue_item_factory.build(payload__bug__id=666)
     dump = item.model_dump()
diff --git a/tests/unit/test_runner.py b/tests/unit/test_runner.py
index f7c8905d..8f5c7bc7 100644
--- a/tests/unit/test_runner.py
+++ b/tests/unit/test_runner.py
@@ -304,6 +304,55 @@ async def test_execute_or_queue_exception(
     mock_queue.track_failed.assert_called_once()
 
 
+@pytest.mark.asyncio
+@pytest.mark.no_mocked_bugzilla
+@pytest.mark.no_mocked_jira
+async def test_execute_or_queue_http_error_details(
+    actions,
+    dl_queue,
+    bugzilla_webhook_request,
+    context_comment_example,
+    mocked_responses,
+):
+    bug = bugzilla_webhook_request.bug
+    settings = get_settings()
+    mocked_responses.add(
+        responses.GET,
+        f"{settings.bugzilla_base_url}/rest/bug/{bug.id}",
+        json={"bugs": [bug.model_dump()]},
+    )
+    mocked_responses.add(
+        responses.GET,
+        f"{settings.bugzilla_base_url}/rest/bug/{bug.id}/comment",
+        json={"bugs": {str(bug.id): {"comments": []}}},
+    )
+    mocked_responses.add(
+        responses.POST,
+        f"{settings.jira_base_url}rest/api/2/issue",
+        json={"key": "TEST-1"},
+    )
+    mocked_responses.add(
+        responses.POST,
+        f"{settings.jira_base_url}rest/api/2/issue/TEST-1/remotelink",
+        status=400,
+        json={
+            "errorMessages": [],
+            "errors": {"resolution": "Field 'resolution' cannot be set."},
+        },
+    )
+
+    await execute_or_queue(
+        request=bugzilla_webhook_request, queue=dl_queue, actions=actions
+    )
+
+    items = (await dl_queue.retrieve())[bug.id]
+    [item] = [i async for i in items]
+    assert (
+        item.error.description
+        == "HTTP 400: resolution: Field 'resolution' cannot be set."
+    )
+
+
 def test_default_invalid_init():
     with pytest.raises(TypeError):
         Executor()