diff --git a/.env.example b/.env.example
index 63623595..10bb9890 100644
--- a/.env.example
+++ b/.env.example
@@ -6,6 +6,8 @@ APP_RELOAD=True
 APP_DEBUG=True
 JBI_API_KEY="fake_api_key"
 DL_QUEUE_DSN=file:///tmp
+DL_QUEUE_CONSTANT_RETRY=true
+DL_QUEUE_RETRY_TIMEOUT_DAYS=7
 
 # Jira API Secrets
 JIRA_USERNAME="fake_jira_username"
diff --git a/.secrets.baseline b/.secrets.baseline
index 37298362..aea8c706 100644
--- a/.secrets.baseline
+++ b/.secrets.baseline
@@ -113,16 +113,16 @@
         "filename": ".env.example",
         "hashed_secret": "4b9a4ce92b6a01a4cd6ee1672d31c043f2ae79ab",
         "is_verified": false,
-        "line_number": 12
+        "line_number": 14
       },
       {
         "type": "Secret Keyword",
         "filename": ".env.example",
         "hashed_secret": "77ea6398f252999314d609a708842a49fc43e055",
         "is_verified": false,
-        "line_number": 15
+        "line_number": 17
       }
     ]
   },
-  "generated_at": "2024-03-20T18:05:17Z"
+  "generated_at": "2024-04-10T20:05:01Z"
 }
diff --git a/Makefile b/Makefile
index cdb82bb6..9dec25a1 100644
--- a/Makefile
+++ b/Makefile
@@ -65,11 +65,11 @@ $(DOTENV_FILE):
 
 .PHONY: docker-shell
 docker-shell: $(DOTENV_FILE)
-	docker-compose run --rm web /bin/sh
+	docker compose run --rm web /bin/sh
 
 .PHONY: docker-start
 docker-start: $(DOTENV_FILE)
-	docker-compose up
+	docker compose up
 
 .PHONY: test
 test: $(INSTALL_STAMP)
diff --git a/docker-compose.yaml b/docker-compose.yaml
index a62d8054..5c10777a 100644
--- a/docker-compose.yaml
+++ b/docker-compose.yaml
@@ -12,3 +12,10 @@ services:
       - ${PORT:-8000}:${PORT:-8000}
     volumes:
       - .:/app
+  retry:
+    build: .
+    command: python -m jbi.retry
+    env_file:
+      - .env
+    volumes:
+      - .:/app
diff --git a/jbi/environment.py b/jbi/environment.py
index fbf5359b..3fe44e3c 100644
--- a/jbi/environment.py
+++ b/jbi/environment.py
@@ -48,9 +48,12 @@ class Settings(BaseSettings):
     sentry_dsn: Optional[AnyUrl] = None
     sentry_traces_sample_rate: float = 1.0
 
+    # Retry queue
     dl_queue_dsn: FileUrl
 
-    model_config = SettingsConfigDict(env_file=".env", env_file_encoding="utf-8")
+    model_config = SettingsConfigDict(
+        env_file=".env", env_file_encoding="utf-8", extra="ignore"
+    )
 
 
 @lru_cache(maxsize=1)
diff --git a/jbi/queue.py b/jbi/queue.py
index 70fd08fe..67425246 100644
--- a/jbi/queue.py
+++ b/jbi/queue.py
@@ -302,6 +302,9 @@ async def list(self, bug_id: int) -> List[str]:
     async def list_all(self) -> dict[int, List[str]]:
         return await self.backend.list_all()
 
+    async def size(self, bug_id=None):
+        return await self.backend.size(bug_id=bug_id)
+
     async def done(self, item: QueueItem) -> None:
         """
         Mark item as done, remove from queue.
diff --git a/jbi/retry.py b/jbi/retry.py
new file mode 100644
index 00000000..77d95286
--- /dev/null
+++ b/jbi/retry.py
@@ -0,0 +1,79 @@
+import asyncio
+import logging
+from datetime import UTC, datetime, timedelta
+from os import getenv
+from time import sleep
+
+import jbi.runner as runner
+from jbi.configuration import ACTIONS
+from jbi.queue import get_dl_queue
+
+CONSTANT_RETRY = getenv("DL_QUEUE_CONSTANT_RETRY", "false") == "true"
+RETRY_TIMEOUT_DAYS = getenv("DL_QUEUE_RETRY_TIMEOUT_DAYS", 7)
+CONSTANT_RETRY_SLEEP = getenv("DL_QUEUE_CONSTANT_RETRY_SLEEP", 5)
+
+logger = logging.getLogger(__name__)
+
+
+async def retry_failed(item_executor=runner.execute_action, queue=get_dl_queue()):
+    min_event_timestamp = datetime.now(UTC) - timedelta(days=int(RETRY_TIMEOUT_DAYS))
+
+    # load all bugs from DLQ
+    bugs = await queue.retrieve()
+
+    # metrics to track
+    metrics = {
+        "bug_count": len(bugs),
+        "events_processed": 0,
+        "events_skipped": 0,
+        "events_failed": 0,
+        "bugs_failed": 0,
+    }
+
+    for bug_id, items in bugs.items():
+        try:
+            async for item in items:
+                # skip and delete item if we have exceeded RETRY_TIMEOUT_DAYS
+                if item.timestamp < min_event_timestamp:
+                    logger.warning("removing expired event %s", item.identifier)
+                    await queue.done(item)
+                    metrics["events_skipped"] += 1
+                    continue
+
+                try:
+                    item_executor(item.payload, ACTIONS)
+                    await queue.done(item)
+                    metrics["events_processed"] += 1
+                except Exception:
+                    logger.exception("failed to reprocess event %s.", item.identifier)
+                    metrics["events_failed"] += 1
+
+                    # check for other events that will be skipped
+                    pending_events = await queue.size(bug_id)
+                    if pending_events > 1:  # if this isn't the only event for the bug
+                        logger.info(
+                            "skipping %d event(s) for bug %d, previous event %s failed",
+                            pending_events - 1,
+                            bug_id,
+                            item.identifier,
+                        )
+                        metrics["events_skipped"] += pending_events - 1
+                        break
+        except Exception:
+            logger.exception("failed to parse events for bug %d.", bug_id)
+            metrics["bugs_failed"] += 1
+
+    return metrics
+
+
+async def main():
+    while True:
+        metrics = await retry_failed()
+        logger.info("event queue processing complete", extra=metrics)
+        if not CONSTANT_RETRY:
+            return
+        sleep(int(CONSTANT_RETRY_SLEEP))
+
+
+if __name__ == "__main__":
+    asyncio.run(main())
diff --git a/tests/unit/test_retry.py b/tests/unit/test_retry.py
new file mode 100644
index 00000000..0c4c94d6
--- /dev/null
+++ b/tests/unit/test_retry.py
@@ -0,0 +1,157 @@
+from datetime import UTC, datetime, timedelta
+from unittest.mock import MagicMock
+
+import pytest
+
+from jbi.queue import DeadLetterQueue
+from jbi.retry import RETRY_TIMEOUT_DAYS, retry_failed
+from jbi.runner import execute_action
+
+
+def iter_error():
+    mock = MagicMock()
+    mock.__aiter__.return_value = None
+    mock.__aiter__.side_effect = Exception("Throwing an exception")
+    return mock
+
+
+async def aiter_sync(iterable):
+    for i in iterable:
+        yield i
+
+
+@pytest.fixture
+def mock_queue():
+    return MagicMock(spec=DeadLetterQueue)
+
+
+@pytest.fixture
+def mock_executor():
+    return MagicMock(spec=execute_action)
+
+
+@pytest.mark.asyncio
+async def test_retry_empty_list(caplog, mock_queue):
+    mock_queue.retrieve.return_value = {}
+
+    metrics = await retry_failed(queue=mock_queue)
+    mock_queue.retrieve.assert_called_once()
+    assert len(caplog.messages) == 0
+    assert metrics == {
+        "bug_count": 0,
+        "events_processed": 0,
+        "events_skipped": 0,
+        "events_failed": 0,
+        "bugs_failed": 0,
+    }
+
+
+@pytest.mark.asyncio
+async def test_retry_success(caplog, mock_queue, mock_executor, queue_item_factory):
+    mock_queue.retrieve.return_value = {
+        1: aiter_sync([queue_item_factory(payload__bug__id=1)])
+    }
+
+    metrics = await retry_failed(item_executor=mock_executor, queue=mock_queue)
+    assert len(caplog.messages) == 0  # no logs should have been generated
+    mock_queue.retrieve.assert_called_once()
+    mock_queue.done.assert_called_once()  # item should be marked as complete
+    mock_executor.assert_called_once()  # item should have been processed
+    assert metrics == {
+        "bug_count": 1,
+        "events_processed": 1,
+        "events_skipped": 0,
+        "events_failed": 0,
+        "bugs_failed": 0,
+    }
+
+
+@pytest.mark.asyncio
+async def test_retry_fail_and_skip(
+    caplog, mock_queue, mock_executor, queue_item_factory
+):
+    mock_queue.retrieve.return_value = {
+        1: aiter_sync(
+            [
+                queue_item_factory(payload__bug__id=1),
+                queue_item_factory(payload__bug__id=1),
+            ]
+        )
+    }
+
+    mock_executor.side_effect = Exception("Throwing an exception")
+    mock_queue.size.return_value = 3
+
+    metrics = await retry_failed(item_executor=mock_executor, queue=mock_queue)
+    mock_queue.retrieve.assert_called_once()
+    mock_queue.done.assert_not_called()  # no items should have been marked as done
+    assert caplog.text.count("failed to reprocess event") == 1
+    assert caplog.text.count("skipping 2 event(s)") == 1
+    assert caplog.text.count("removing expired event") == 0
+    mock_executor.assert_called_once()  # only one item should have been attempted to be processed
+    assert metrics == {
+        "bug_count": 1,
+        "events_processed": 0,
+        "events_skipped": 2,
+        "events_failed": 1,
+        "bugs_failed": 0,
+    }
+
+
+@pytest.mark.asyncio
+async def test_retry_remove_expired(
+    caplog, mock_queue, mock_executor, queue_item_factory
+):
+    mock_queue.retrieve.return_value = {
+        1: aiter_sync(
+            [
+                queue_item_factory(
+                    payload__bug__id=1,
+                    payload__event__time=datetime.now(UTC)
+                    - timedelta(days=int(RETRY_TIMEOUT_DAYS), seconds=1),
+                ),
+                queue_item_factory(payload__bug__id=1),
+            ]
+        )
+    }
+
+    metrics = await retry_failed(item_executor=mock_executor, queue=mock_queue)
+    mock_queue.retrieve.assert_called_once()
+    assert (
+        len(mock_queue.done.call_args_list) == 2
+    ), "both items should have been marked as done"
+    assert caplog.text.count("failed to reprocess event") == 0
+    assert caplog.text.count("skipping events") == 0
+    assert caplog.text.count("removing expired event") == 1
+    mock_executor.assert_called_once()  # only one item should have been attempted to be processed
+    assert metrics == {
+        "bug_count": 1,
+        "events_processed": 1,
+        "events_skipped": 1,
+        "events_failed": 0,
+        "bugs_failed": 0,
+    }
+
+
+@pytest.mark.asyncio
+async def test_retry_bug_failed(caplog, mock_queue, mock_executor, queue_item_factory):
+    mock_queue.retrieve.return_value = {
+        1: aiter_sync([queue_item_factory(payload__bug__id=1)]),
+        2: iter_error(),
+    }
+
+    metrics = await retry_failed(item_executor=mock_executor, queue=mock_queue)
+    mock_queue.retrieve.assert_called_once()
+    mock_queue.done.assert_called_once()  # one item should have been marked as done
+    assert caplog.text.count("failed to reprocess event") == 0
+    assert caplog.text.count("skipping events") == 0
+    assert caplog.text.count("removing expired event") == 0
+    assert caplog.text.count("failed to parse events for bug") == 1
+    mock_executor.assert_called_once()  # only one item should have been attempted to be processed
+    assert metrics == {
+        "bug_count": 2,
+        "events_processed": 1,
+        "events_skipped": 0,
+        "events_failed": 0,
+        "bugs_failed": 1,
+    }