diff --git a/airbyte-ci/connectors/metadata_service/orchestrator/orchestrator/__init__.py b/airbyte-ci/connectors/metadata_service/orchestrator/orchestrator/__init__.py
index 4754c2183383..761da4c7b092 100644
--- a/airbyte-ci/connectors/metadata_service/orchestrator/orchestrator/__init__.py
+++ b/airbyte-ci/connectors/metadata_service/orchestrator/orchestrator/__init__.py
@@ -5,7 +5,13 @@
 from dagster_slack import SlackResource
 
 from orchestrator.resources.gcp import gcp_gcs_client, gcs_directory_blobs, gcs_file_blob, gcs_file_manager
-from orchestrator.resources.github import github_client, github_connector_repo, github_connectors_directory, github_workflow_runs
+from orchestrator.resources.github import (
+    github_client,
+    github_connector_repo,
+    github_connectors_directory,
+    github_workflow_runs,
+    github_connectors_metadata_files,
+)
 
 from orchestrator.assets import (
     connector_test_report,
@@ -25,6 +31,7 @@
     add_new_metadata_partitions,
 )
 from orchestrator.jobs.connector_test_report import generate_nightly_reports, generate_connector_test_summary_reports
+from orchestrator.jobs.metadata import generate_stale_gcs_latest_metadata_file
 from orchestrator.sensors.registry import registry_updated_sensor
 from orchestrator.sensors.gcs import new_gcs_blobs_sensor
 from orchestrator.logging.sentry import setup_dagster_sentry
@@ -64,6 +71,7 @@
     "github_client": github_client.configured({"github_token": {"env": "GITHUB_METADATA_SERVICE_TOKEN"}}),
     "github_connector_repo": github_connector_repo.configured({"connector_repo_name": CONNECTOR_REPO_NAME}),
     "github_connectors_directory": github_connectors_directory.configured({"connectors_path": CONNECTORS_PATH}),
+    "github_connectors_metadata_files": github_connectors_metadata_files.configured({"connectors_path": CONNECTORS_PATH}),
     "github_connector_nightly_workflow_successes": github_workflow_runs.configured(
         {
             "workflow_id": NIGHTLY_GHA_WORKFLOW_ID,
@@ -168,6 +176,11 @@
 SCHEDULES = [
     ScheduleDefinition(job=add_new_metadata_partitions, cron_schedule="*/5 * * * *", tags={"dagster/priority": HIGH_QUEUE_PRIORITY}),
     ScheduleDefinition(job=generate_connector_test_summary_reports, cron_schedule="@hourly"),
+    ScheduleDefinition(
+        cron_schedule="0 8 * * *", # Daily at 8am US/Pacific
+        execution_timezone="US/Pacific",
+        job=generate_stale_gcs_latest_metadata_file,
+    ),
 ]
 
 JOBS = [
@@ -177,6 +190,7 @@
     generate_registry_entry,
     generate_nightly_reports,
     add_new_metadata_partitions,
+    generate_stale_gcs_latest_metadata_file,
 ]
 
 """
diff --git a/airbyte-ci/connectors/metadata_service/orchestrator/orchestrator/assets/github.py b/airbyte-ci/connectors/metadata_service/orchestrator/orchestrator/assets/github.py
index 33b3a29d126d..54d4696b0d3d 100644
--- a/airbyte-ci/connectors/metadata_service/orchestrator/orchestrator/assets/github.py
+++ b/airbyte-ci/connectors/metadata_service/orchestrator/orchestrator/assets/github.py
@@ -1,5 +1,15 @@
-from dagster import Output, asset, OpExecutionContext
 import pandas as pd
+import hashlib
+import base64
+import dateutil
+import datetime
+import humanize
+import os
+
+from dagster import Output, asset, OpExecutionContext
+from github import Repository
+
+from orchestrator.ops.slack import send_slack_message
 from orchestrator.utils.dagster_helpers import OutputDataFrame, output_dataframe
 from orchestrator.logging import sentry
 
@@ -7,6 +17,21 @@
 GROUP_NAME = "github"
 
 
+def _get_md5_of_github_file(context: OpExecutionContext, github_connector_repo: Repository, path: str) -> str:
+    """
+    Return the md5 hash of a file in the github repo.
+    """
+    context.log.debug(f"retrieving contents of {path}")
+    file_contents = github_connector_repo.get_contents(path)
+
+    # calculate the md5 hash of the file contents
+    context.log.debug(f"calculating md5 hash of {path}")
+    md5_hash = hashlib.md5()
+    md5_hash.update(file_contents.decoded_content)
+    base_64_value = base64.b64encode(md5_hash.digest()).decode("utf8")
+    return base_64_value
+
+
 @asset(required_resource_keys={"github_connectors_directory"}, group_name=GROUP_NAME)
 @sentry.instrument_asset_op
 def github_connector_folders(context):
@@ -19,6 +44,93 @@ def github_connector_folders(context):
     return Output(folder_names, metadata={"preview": folder_names})
 
 
+@asset(required_resource_keys={"github_connector_repo", "github_connectors_metadata_files"}, group_name=GROUP_NAME)
+def github_metadata_file_md5s(context):
+    """
+    Return a list of all the folders in the github connectors directory.
+    """
+    github_connector_repo = context.resources.github_connector_repo
+    github_connectors_metadata_files = context.resources.github_connectors_metadata_files
+
+    metadata_file_paths = {
+        metadata_file["path"]: {
+            "md5": _get_md5_of_github_file(context, github_connector_repo, metadata_file["path"]),
+            "last_modified": metadata_file["last_modified"],
+        }
+        for metadata_file in github_connectors_metadata_files
+    }
+
+    return Output(metadata_file_paths, metadata={"preview": metadata_file_paths})
+
+def _should_publish_have_ran(datetime_string: str) -> bool:
+    """
+    Return true if the datetime is 2 hours old.
+
+    """
+    dt = dateutil.parser.parse(datetime_string)
+    now = datetime.datetime.now(datetime.timezone.utc)
+    two_hours_ago = now - datetime.timedelta(hours=2)
+    return dt < two_hours_ago
+
+def _to_time_ago(datetime_string: str) -> str:
+    """
+    Return a string of how long ago the datetime is human readable format. 10 min
+    """
+    dt = dateutil.parser.parse(datetime_string)
+    return humanize.naturaltime(dt)
+
+
+def _is_stale(github_file_info: dict, latest_gcs_metadata_md5s: dict) -> bool:
+    """
+    Return true if the github info is stale.
+    """
+    not_in_gcs = latest_gcs_metadata_md5s.get(github_file_info["md5"]) is None
+    return not_in_gcs and _should_publish_have_ran(github_file_info["last_modified"])
+
+@asset(required_resource_keys={"slack", "latest_metadata_file_blobs"}, group_name=GROUP_NAME)
+def stale_gcs_latest_metadata_file(context, github_metadata_file_md5s: dict) -> OutputDataFrame:
+    """
+    Return a list of all metadata files in the github repo and denote whether they are stale or not.
+
+    Stale means that the file in the github repo is not in the latest metadata file blobs.
+    """
+    human_readable_stale_bools = {True: "🚨 YES!!!", False: "No"}
+    latest_gcs_metadata_file_blobs = context.resources.latest_metadata_file_blobs
+    latest_gcs_metadata_md5s = {blob.md5_hash: blob.name for blob in latest_gcs_metadata_file_blobs}
+
+    stale_report = [
+        {
+            "stale": _is_stale(github_file_info, latest_gcs_metadata_md5s),
+            "github_path": github_path,
+            "github_md5": github_file_info["md5"],
+            "github_last_modified": _to_time_ago(github_file_info["last_modified"]),
+            "gcs_md5": latest_gcs_metadata_md5s.get(github_file_info["md5"]),
+            "gcs_path": latest_gcs_metadata_md5s.get(github_file_info["md5"]),
+        }
+        for github_path, github_file_info in github_metadata_file_md5s.items()
+    ]
+
+    stale_metadata_files_df = pd.DataFrame(stale_report)
+
+    # sort by stale true to false, then by github_path
+    stale_metadata_files_df = stale_metadata_files_df.sort_values(
+        by=["stale", "github_path"],
+        ascending=[False, True],
+    )
+
+    # If any stale files exist, report to slack
+    channel = os.getenv("STALE_REPORT_CHANNEL")
+    any_stale = stale_metadata_files_df["stale"].any()
+    if channel and any_stale:
+        only_stale_df = stale_metadata_files_df[stale_metadata_files_df["stale"] == True]
+        pretty_stale_df = only_stale_df.replace(human_readable_stale_bools)
+        stale_report_md = pretty_stale_df.to_markdown(index=False)
+        send_slack_message(context, channel, stale_report_md, enable_code_block_wrapping=True)
+
+    stale_metadata_files_df.replace(human_readable_stale_bools, inplace=True)
+    return output_dataframe(stale_metadata_files_df)
+
+
 @asset(required_resource_keys={"github_connector_nightly_workflow_successes"}, group_name=GROUP_NAME)
 @sentry.instrument_asset_op
 def github_connector_nightly_workflow_successes(context: OpExecutionContext) -> OutputDataFrame:
diff --git a/airbyte-ci/connectors/metadata_service/orchestrator/orchestrator/jobs/metadata.py b/airbyte-ci/connectors/metadata_service/orchestrator/orchestrator/jobs/metadata.py
new file mode 100644
index 000000000000..071f1cb3c6a5
--- /dev/null
+++ b/airbyte-ci/connectors/metadata_service/orchestrator/orchestrator/jobs/metadata.py
@@ -0,0 +1,4 @@
+from dagster import define_asset_job, AssetSelection
+
+stale_gcs_latest_metadata_file_inclusive = AssetSelection.keys("stale_gcs_latest_metadata_file").upstream()
+generate_stale_gcs_latest_metadata_file = define_asset_job(name="generate_stale_metadata_report", selection=stale_gcs_latest_metadata_file_inclusive)
diff --git a/airbyte-ci/connectors/metadata_service/orchestrator/orchestrator/resources/github.py b/airbyte-ci/connectors/metadata_service/orchestrator/orchestrator/resources/github.py
index 9b0e125aeff0..2227ed3cc67f 100644
--- a/airbyte-ci/connectors/metadata_service/orchestrator/orchestrator/resources/github.py
+++ b/airbyte-ci/connectors/metadata_service/orchestrator/orchestrator/resources/github.py
@@ -1,8 +1,17 @@
 from typing import List
 from dagster import StringSource, InitResourceContext, resource
-from github import Github, Repository, ContentFile
+from github import Github, Repository, ContentFile, GitTreeElement
 from datetime import datetime, timedelta
+from dateutil.parser import parse
 
+from orchestrator.config import CONNECTORS_PATH
+from metadata_service.constants import METADATA_FILE_NAME
+
+def _valid_metadata_file_path(path: str) -> bool:
+    """
+    Ensure that the path is a metadata file and not a scaffold file.
+    """
+    return METADATA_FILE_NAME in path and CONNECTORS_PATH in path and "-scaffold-" not in path
 
 @resource(
     config_schema={"github_token": StringSource},
@@ -36,6 +45,25 @@ def github_connectors_directory(resource_context: InitResourceContext) -> List[C
     return github_connector_repo.get_contents(connectors_path)
 
 
+@resource(
+    required_resource_keys={"github_connector_repo"},
+    config_schema={"connectors_path": StringSource},
+)
+def github_connectors_metadata_files(resource_context: InitResourceContext) -> List[dict]:
+    resource_context.log.info(f"retrieving github metadata files")
+
+    github_connector_repo = resource_context.resources.github_connector_repo
+    repo_file_tree = github_connector_repo.get_git_tree("master", recursive=True).tree
+    metadata_file_paths = [{
+        "path": github_file.path,
+        "sha": github_file.sha,
+        "last_modified": github_file.last_modified
+    } for github_file in repo_file_tree if _valid_metadata_file_path(github_file.path)]
+
+    resource_context.log.info(f"finished retrieving github metadata files")
+    return metadata_file_paths
+
+
 @resource(
     required_resource_keys={"github_connector_repo"},
     config_schema={
diff --git a/airbyte-ci/connectors/metadata_service/orchestrator/poetry.lock b/airbyte-ci/connectors/metadata_service/orchestrator/poetry.lock
index 538ec28d61aa..fafe163819a5 100644
--- a/airbyte-ci/connectors/metadata_service/orchestrator/poetry.lock
+++ b/airbyte-ci/connectors/metadata_service/orchestrator/poetry.lock
@@ -2,13 +2,13 @@
 
 [[package]]
 name = "alembic"
-version = "1.11.1"
+version = "1.11.2"
 description = "A database migration tool for SQLAlchemy."
 optional = false
 python-versions = ">=3.7"
 files = [
-    {file = "alembic-1.11.1-py3-none-any.whl", hash = "sha256:dc871798a601fab38332e38d6ddb38d5e734f60034baeb8e2db5b642fccd8ab8"},
-    {file = "alembic-1.11.1.tar.gz", hash = "sha256:6a810a6b012c88b33458fceb869aef09ac75d6ace5291915ba7fae44de372c01"},
+    {file = "alembic-1.11.2-py3-none-any.whl", hash = "sha256:7981ab0c4fad4fe1be0cf183aae17689fe394ff874fd2464adb774396faf0796"},
+    {file = "alembic-1.11.2.tar.gz", hash = "sha256:678f662130dc540dac12de0ea73de9f89caea9dbea138f60ef6263149bf84657"},
 ]
 
 [package.dependencies]
@@ -466,31 +466,31 @@ test-randomorder = ["pytest-randomly"]
 
 [[package]]
 name = "dagit"
-version = "1.4.3"
+version = "1.4.4"
 description = "Web UI for dagster."
 optional = false
 python-versions = "*"
 files = [
-    {file = "dagit-1.4.3-py3-none-any.whl", hash = "sha256:110dc66d81478cf0ffcbab0ad1f2829bae685c32008e2e7ef156ee987816c08e"},
-    {file = "dagit-1.4.3.tar.gz", hash = "sha256:552dc3abdaec71b90d0fba22495d50c25597ba2dba2c373b426698559993e1c5"},
+    {file = "dagit-1.4.4-py3-none-any.whl", hash = "sha256:cf10a16546c6e81618af9cc6cbe8a1914c8e60df191c1fdd38c3ce8e874f64a5"},
+    {file = "dagit-1.4.4.tar.gz", hash = "sha256:83778973f07b97ae415ecc67c86ee502395e7d882d474827a4e914766122dbf3"},
 ]
 
 [package.dependencies]
-dagster-webserver = "1.4.3"
+dagster-webserver = "1.4.4"
 
 [package.extras]
-notebook = ["dagster-webserver[notebook] (==1.4.3)"]
-test = ["dagster-webserver[test] (==1.4.3)"]
+notebook = ["dagster-webserver[notebook] (==1.4.4)"]
+test = ["dagster-webserver[test] (==1.4.4)"]
 
 [[package]]
 name = "dagster"
-version = "1.4.3"
+version = "1.4.4"
 description = "The data orchestration platform built for productivity."
 optional = false
 python-versions = "*"
 files = [
-    {file = "dagster-1.4.3-py3-none-any.whl", hash = "sha256:d16c46d27d91ed10e37c35f406bb5a6a349b7b6e2d92443d09d97a78cd079c52"},
-    {file = "dagster-1.4.3.tar.gz", hash = "sha256:eb0c9870c3f2e072688c4423d4dfb2dac670870cd1c5e39806f1384f71336c9c"},
+    {file = "dagster-1.4.4-py3-none-any.whl", hash = "sha256:8790005fef7d21e65bdf206908706b486181365b908242edf6d0d06a97901a75"},
+    {file = "dagster-1.4.4.tar.gz", hash = "sha256:4e4d07609489b3499ab4d3f0b24796f860c57f35d5234d73bc6869f1dda39d47"},
 ]
 
 [package.dependencies]
@@ -520,7 +520,7 @@ tomli = "*"
 toposort = ">=1.0"
 tqdm = "*"
 typing-extensions = ">=4.4.0"
-universal-pathlib = "*"
+universal-pathlib = "<0.1.0"
 watchdog = ">=0.8.3"
 
 [package.extras]
@@ -533,41 +533,41 @@ test = ["buildkite-test-collector", "docker", "grpcio-tools (>=1.44.0)", "mock (
 
 [[package]]
 name = "dagster-cloud"
-version = "1.4.3"
+version = "1.4.4"
 description = ""
 optional = false
 python-versions = "*"
 files = [
-    {file = "dagster_cloud-1.4.3-py3-none-any.whl", hash = "sha256:5f55ffb61ee232fc442f0c1c2050034790e0d9b04cd3601b9e4b48cfaddcf126"},
-    {file = "dagster_cloud-1.4.3.tar.gz", hash = "sha256:2b87d3ea5f5f52ec4af4fef4c33440554bd1eaa381f634f51f28b42fedc5a2ad"},
+    {file = "dagster_cloud-1.4.4-py3-none-any.whl", hash = "sha256:fe0c1a098530d33cdb440dc29d6ae55fdcc02eb1e7ce3a6ea4582342881a6842"},
+    {file = "dagster_cloud-1.4.4.tar.gz", hash = "sha256:047cf1dacac012311252cfb505f1229e912e3e175a9cbe0549ae6b3facfd5417"},
 ]
 
 [package.dependencies]
-dagster = "1.4.3"
-dagster-cloud-cli = "1.4.3"
+dagster = "1.4.4"
+dagster-cloud-cli = "1.4.4"
 pex = "*"
 questionary = "*"
 requests = "*"
 typer = {version = "*", extras = ["all"]}
 
 [package.extras]
-docker = ["dagster-docker (==0.20.3)", "docker"]
-ecs = ["boto3", "dagster-aws (==0.20.3)"]
-kubernetes = ["dagster-k8s (==0.20.3)", "kubernetes"]
+docker = ["dagster-docker (==0.20.4)", "docker"]
+ecs = ["boto3", "dagster-aws (==0.20.4)"]
+kubernetes = ["dagster-k8s (==0.20.4)", "kubernetes"]
 pex = ["boto3"]
 sandbox = ["supervisor"]
 serverless = ["boto3"]
-tests = ["black", "dagster-cloud-test-infra", "dagster-k8s (==0.20.3)", "docker", "httpretty", "isort", "kubernetes", "moto[all]", "mypy", "paramiko", "pylint", "pytest", "types-PyYAML", "types-requests"]
+tests = ["black", "dagster-cloud-test-infra", "dagster-k8s (==0.20.4)", "docker", "httpretty", "isort", "kubernetes", "moto[all]", "mypy", "paramiko", "pylint", "pytest", "types-PyYAML", "types-requests"]
 
 [[package]]
 name = "dagster-cloud-cli"
-version = "1.4.3"
+version = "1.4.4"
 description = ""
 optional = false
 python-versions = "*"
 files = [
-    {file = "dagster_cloud_cli-1.4.3-py3-none-any.whl", hash = "sha256:1fb92d4a1fe4d2582ccf51230e2039338139dd22b58022ba454cbd12e4ebf6fd"},
-    {file = "dagster_cloud_cli-1.4.3.tar.gz", hash = "sha256:0536d99cdf9b56ffc3bec26a7dac814e700d12e9e96e180ec8d62d92c52296b7"},
+    {file = "dagster_cloud_cli-1.4.4-py3-none-any.whl", hash = "sha256:f38f230bb21a4535765762f92b5d06438a507da7bab57fe7db91c27cc70fe60f"},
+    {file = "dagster_cloud_cli-1.4.4.tar.gz", hash = "sha256:6ae9f5bd1b9235108c6131551752953a88613e71c20d9b4086597c8a9966f2a4"},
 ]
 
 [package.dependencies]
@@ -583,18 +583,18 @@ tests = ["freezegun"]
 
 [[package]]
 name = "dagster-gcp"
-version = "0.20.3"
+version = "0.20.4"
 description = "Package for GCP-specific Dagster framework op and resource components."
 optional = false
 python-versions = "*"
 files = [
-    {file = "dagster-gcp-0.20.3.tar.gz", hash = "sha256:b0ec46a1e01933dfc7d73592ba2243a7b7923c79f9da809fd38580b2ccb2ef0d"},
-    {file = "dagster_gcp-0.20.3-py3-none-any.whl", hash = "sha256:861bcfafd739f61689dbb031b037760231ed4604f4c3b2b79b607781fa61e2fb"},
+    {file = "dagster-gcp-0.20.4.tar.gz", hash = "sha256:b3c76ea8398a41016e58374cd9699514ae1903e503b426347dea17adca0ea758"},
+    {file = "dagster_gcp-0.20.4-py3-none-any.whl", hash = "sha256:2cb241f47e98cfbc3f3c2af64e7260923c6ba717929f672f4a039ec988b0de61"},
 ]
 
 [package.dependencies]
-dagster = "1.4.3"
-dagster-pandas = "0.20.3"
+dagster = "1.4.4"
+dagster-pandas = "0.20.4"
 db-dtypes = "*"
 google-api-python-client = "*"
 google-cloud-bigquery = "*"
@@ -606,17 +606,17 @@ pyarrow = ["pyarrow"]
 
 [[package]]
 name = "dagster-graphql"
-version = "1.4.3"
+version = "1.4.4"
 description = "The GraphQL frontend to python dagster."
 optional = false
 python-versions = "*"
 files = [
-    {file = "dagster-graphql-1.4.3.tar.gz", hash = "sha256:75d745774ce66d800654428ddba7e80a16917e3440b32606c8643de09f4b9363"},
-    {file = "dagster_graphql-1.4.3-py3-none-any.whl", hash = "sha256:637c32584429b1bd81a753048b26a874c13a863cd89d968efbc9c9e4528e2f46"},
+    {file = "dagster-graphql-1.4.4.tar.gz", hash = "sha256:7ca85756393aa6a4d0c2a43044e3a0d3e3a61bffb527fa82c936126296bfb5c6"},
+    {file = "dagster_graphql-1.4.4-py3-none-any.whl", hash = "sha256:f919459f1edb8be2e1d02a28fa3600869a27be5d52d66eb253902e155d1a5a04"},
 ]
 
 [package.dependencies]
-dagster = "1.4.3"
+dagster = "1.4.4"
 gql = {version = ">=3.0.0", extras = ["requests"]}
 graphene = ">=3"
 requests = "*"
@@ -625,49 +625,49 @@ urllib3 = "<2.0.0"
 
 [[package]]
 name = "dagster-pandas"
-version = "0.20.3"
+version = "0.20.4"
 description = "Utilities and examples for working with pandas and dagster, an opinionated framework for expressing data pipelines"
 optional = false
 python-versions = "*"
 files = [
-    {file = "dagster-pandas-0.20.3.tar.gz", hash = "sha256:4ee73b13ee6b70fb5d2fc0131ba2ee1dd22ec9feeb23f95b71930a16b868aa51"},
-    {file = "dagster_pandas-0.20.3-py3-none-any.whl", hash = "sha256:18b61825475b1b1e5be110dcf035d1ceb8292e94b54335a9caf920ded8697284"},
+    {file = "dagster-pandas-0.20.4.tar.gz", hash = "sha256:954055ce711017e151f3a3f0466d99d55ffc16bf4554e357777d7a02e3413993"},
+    {file = "dagster_pandas-0.20.4-py3-none-any.whl", hash = "sha256:f5e37ad885cd44e79f06eae412792b6284f9a0568f4ba606f895fe467cccaf74"},
 ]
 
 [package.dependencies]
-dagster = "1.4.3"
+dagster = "1.4.4"
 pandas = "*"
 
 [[package]]
 name = "dagster-slack"
-version = "0.20.3"
+version = "0.20.4"
 description = "A Slack client resource for posting to Slack"
 optional = false
 python-versions = "*"
 files = [
-    {file = "dagster-slack-0.20.3.tar.gz", hash = "sha256:0a8fa894a596ff6398d4043c832199e4392d315a189e0ccd6dbdf7213ba6fe14"},
-    {file = "dagster_slack-0.20.3-py3-none-any.whl", hash = "sha256:558b3627193f30aa26be5326b357b9e1382c2c31e946c25ab206f03797ce71ae"},
+    {file = "dagster-slack-0.20.4.tar.gz", hash = "sha256:c0a8dcedd722f4d0f15eb4322d6a0160f0360e24e1bfffc612624f967b99e3d2"},
+    {file = "dagster_slack-0.20.4-py3-none-any.whl", hash = "sha256:4e418012bd94fda8303044282aedaec1d11ce697f7495161f23b745885223914"},
 ]
 
 [package.dependencies]
-dagster = "1.4.3"
+dagster = "1.4.4"
 slack-sdk = "*"
 
 [[package]]
 name = "dagster-webserver"
-version = "1.4.3"
+version = "1.4.4"
 description = "Web UI for dagster."
 optional = false
 python-versions = "*"
 files = [
-    {file = "dagster_webserver-1.4.3-py3-none-any.whl", hash = "sha256:70c9cb633d6b782ef4b93a950ce05393c3b84dc567af49bf740eb870cc7ab0a6"},
-    {file = "dagster_webserver-1.4.3.tar.gz", hash = "sha256:c046a8798e929474063f9bae211f35a44a157d9ac91222dabd0c42284d814be0"},
+    {file = "dagster_webserver-1.4.4-py3-none-any.whl", hash = "sha256:80ebb430617a1949c7d3019fd2cc29178467d1d6b8136bd09b64fb13ba09103a"},
+    {file = "dagster_webserver-1.4.4.tar.gz", hash = "sha256:3b1b0316d5937478f8ff734c2de10e2f5ae3da500fbdea47948947496fc60646"},
 ]
 
 [package.dependencies]
 click = ">=7.0,<9.0"
-dagster = "1.4.3"
-dagster-graphql = "1.4.3"
+dagster = "1.4.4"
+dagster-graphql = "1.4.4"
 starlette = "*"
 uvicorn = {version = "*", extras = ["standard"]}
 
@@ -1683,6 +1683,20 @@ files = [
 [package.dependencies]
 pyreadline3 = {version = "*", markers = "sys_platform == \"win32\" and python_version >= \"3.8\""}
 
+[[package]]
+name = "humanize"
+version = "4.7.0"
+description = "Python humanize utilities"
+optional = false
+python-versions = ">=3.8"
+files = [
+    {file = "humanize-4.7.0-py3-none-any.whl", hash = "sha256:df7c429c2d27372b249d3f26eb53b07b166b661326e0325793e0a988082e3889"},
+    {file = "humanize-4.7.0.tar.gz", hash = "sha256:7ca0e43e870981fa684acb5b062deb307218193bca1a01f2b2676479df849b3a"},
+]
+
+[package.extras]
+tests = ["freezegun", "pytest", "pytest-cov"]
+
 [[package]]
 name = "idna"
 version = "3.4"
@@ -2022,13 +2036,13 @@ url = "../lib"
 
 [[package]]
 name = "more-itertools"
-version = "10.0.0"
+version = "10.1.0"
 description = "More routines for operating on iterables, beyond itertools"
 optional = false
 python-versions = ">=3.8"
 files = [
-    {file = "more-itertools-10.0.0.tar.gz", hash = "sha256:cd65437d7c4b615ab81c0640c0480bc29a550ea032891977681efd28344d51e1"},
-    {file = "more_itertools-10.0.0-py3-none-any.whl", hash = "sha256:928d514ffd22b5b0a8fce326d57f423a55d2ff783b093bab217eda71e732330f"},
+    {file = "more-itertools-10.1.0.tar.gz", hash = "sha256:626c369fa0eb37bac0291bce8259b332fd59ac792fa5497b59837309cd5b114a"},
+    {file = "more_itertools-10.1.0-py3-none-any.whl", hash = "sha256:64e0735fcfdc6f3464ea133afe8ea4483b1c5fe3a3d69852e6503b43a0b222e6"},
 ]
 
 [[package]]
@@ -3209,13 +3223,13 @@ full = ["numpy"]
 
 [[package]]
 name = "referencing"
-version = "0.30.0"
+version = "0.30.1"
 description = "JSON Referencing + Python"
 optional = false
 python-versions = ">=3.8"
 files = [
-    {file = "referencing-0.30.0-py3-none-any.whl", hash = "sha256:c257b08a399b6c2f5a3510a50d28ab5dbc7bbde049bcaf954d43c446f83ab548"},
-    {file = "referencing-0.30.0.tar.gz", hash = "sha256:47237742e990457f7512c7d27486394a9aadaf876cbfaa4be65b27b4f4d47c6b"},
+    {file = "referencing-0.30.1-py3-none-any.whl", hash = "sha256:185d4a29f001c6e8ae4dad3861e61282a81cb01b9f0ef70a15450c45c6513a0d"},
+    {file = "referencing-0.30.1.tar.gz", hash = "sha256:9370c77ceefd39510d70948bbe7375ce2d0125b9c11fd380671d4de959a8e3ce"},
 ]
 
 [package.dependencies]
@@ -3749,20 +3763,20 @@ files = [
 
 [[package]]
 name = "universal-pathlib"
-version = "0.1.0"
+version = "0.0.24"
 description = "pathlib api extended to use fsspec backends"
 optional = false
 python-versions = ">=3.8"
 files = [
-    {file = "universal_pathlib-0.1.0-py3-none-any.whl", hash = "sha256:307cf3963eb2396728aca76c3c886e3e73d6569bd4dfa399c954b617a972dd4d"},
-    {file = "universal_pathlib-0.1.0.tar.gz", hash = "sha256:2eace58c8654661f331ef73206a14705bba7a4955816993a99fb9eb151b2a238"},
+    {file = "universal_pathlib-0.0.24-py3-none-any.whl", hash = "sha256:a2e907b11b1b3f6e982275e5ac0c58a4d34dba2b9e703ecbe2040afa572c741b"},
+    {file = "universal_pathlib-0.0.24.tar.gz", hash = "sha256:fcbffb95e4bc69f704af5dde4f9a624b2269f251a38c81ab8bec19dfeaad830f"},
 ]
 
 [package.dependencies]
 fsspec = "*"
 
 [package.extras]
-dev = ["adlfs", "aiohttp", "cheroot", "gcsfs", "hadoop-test-cluster", "moto[s3,server]", "mypy (==1.3.0)", "pyarrow", "pydantic", "pydantic-settings", "pylint (==2.17.4)", "pytest (==7.3.2)", "pytest-cov (==4.1.0)", "pytest-mock (==3.11.1)", "pytest-sugar (==0.9.6)", "requests", "s3fs", "webdav4[fsspec]", "wsgidav"]
+dev = ["adlfs", "aiohttp", "cheroot", "gcsfs", "hadoop-test-cluster", "moto[s3,server]", "mypy (==1.3.0)", "pyarrow", "pylint (==2.17.4)", "pytest (==7.3.2)", "pytest-cov (==4.1.0)", "pytest-mock (==3.11.1)", "pytest-sugar (==0.9.6)", "requests", "s3fs", "webdav4[fsspec]", "wsgidav"]
 tests = ["mypy (==1.3.0)", "pylint (==2.17.4)", "pytest (==7.3.2)", "pytest-cov (==4.1.0)", "pytest-mock (==3.11.1)", "pytest-sugar (==0.9.6)"]
 
 [[package]]
@@ -4339,4 +4353,4 @@ testing = ["big-O", "jaraco.functools", "jaraco.itertools", "more-itertools", "p
 [metadata]
 lock-version = "2.0"
 python-versions = "^3.9"
-content-hash = "006df8f9463d714cceaa9041f0a2f542bbb12beb5681fb21fb5f850a93eacd04"
+content-hash = "8c6fa8dc9750af9e32ac39bfb45a960721098d735bd81f5baf8134921127f16d"
diff --git a/airbyte-ci/connectors/metadata_service/orchestrator/pyproject.toml b/airbyte-ci/connectors/metadata_service/orchestrator/pyproject.toml
index 837c9b74569b..36eb30b42eff 100644
--- a/airbyte-ci/connectors/metadata_service/orchestrator/pyproject.toml
+++ b/airbyte-ci/connectors/metadata_service/orchestrator/pyproject.toml
@@ -28,6 +28,8 @@ pydantic = "^1.10.6"
 dagster-slack = "^0.20.2"
 sentry-sdk = "^1.28.1"
 semver = "^3.0.1"
+python-dateutil = "^2.8.2"
+humanize = "^4.7.0"
 
 
 [tool.poetry.group.dev.dependencies]
diff --git a/airbyte-ci/connectors/metadata_service/orchestrator/tests/test_debug.py b/airbyte-ci/connectors/metadata_service/orchestrator/tests/test_debug.py
index 3cfc0bc7bbfa..bf46d5321099 100644
--- a/airbyte-ci/connectors/metadata_service/orchestrator/tests/test_debug.py
+++ b/airbyte-ci/connectors/metadata_service/orchestrator/tests/test_debug.py
@@ -4,8 +4,9 @@
 from orchestrator.assets.connector_test_report import generate_nightly_report, persist_connectors_test_summary_files
 from orchestrator.assets.registry_entry import registry_entry, metadata_entry
 from orchestrator.assets.registry import persisted_oss_registry
+from orchestrator.assets.github import github_metadata_file_md5s, stale_gcs_latest_metadata_file
 from orchestrator.config import NIGHTLY_INDIVIDUAL_TEST_REPORT_FILE_NAME, NIGHTLY_FOLDER, NIGHTLY_COMPLETE_REPORT_FILE_NAME, REPORT_FOLDER
-from orchestrator import REGISTRY_ENTRY_RESOURCE_TREE
+from orchestrator import REGISTRY_ENTRY_RESOURCE_TREE, GITHUB_RESOURCE_TREE, METADATA_RESOURCE_TREE
 from metadata_service.constants import METADATA_FILE_NAME, METADATA_FOLDER
 
 
@@ -37,6 +38,17 @@ def debug_registry():
     persisted_oss_registry(context).value
 
 
+def debug_github_folders():
+    context = build_op_context(
+        resources={
+            **GITHUB_RESOURCE_TREE,
+            **METADATA_RESOURCE_TREE,
+        }
+    )
+    github_md5s = github_metadata_file_md5s(context).value
+    stale_gcs_latest_metadata_file(context, github_md5s).value
+
+
 def debug_badges():
     resources = {
         "gcp_gcs_client": gcp_gcs_client.configured(