diff --git a/estuary-cdk/estuary_cdk/__init__.py b/estuary-cdk/estuary_cdk/__init__.py
index 591d48e77b..bf4b7d8297 100644
--- a/estuary-cdk/estuary_cdk/__init__.py
+++ b/estuary-cdk/estuary_cdk/__init__.py
@@ -95,6 +95,11 @@ def dump_all_tasks(signum, frame):
                 if task is this_task:
                     continue
 
+                log.info("Attempting to inject SIGQUIT exception into task.", {
+                    "task.get_name()": task.get_name(),
+                    "task.get_coro().__name__": task.get_coro().__name__,
+                })
+
                 # Reach inside the task coroutine to inject an exception, which
                 # will unwind the task stack and lets us print a precise stack trace.
                 try:
diff --git a/estuary-cdk/estuary_cdk/requests_session_send_patch.py b/estuary-cdk/estuary_cdk/requests_session_send_patch.py
new file mode 100644
index 0000000000..e4fbcbdcdb
--- /dev/null
+++ b/estuary-cdk/estuary_cdk/requests_session_send_patch.py
@@ -0,0 +1,15 @@
+import requests
+
+# Airbyte's CDK does not set a timeout for HTTP requests, so we patch it to always have a timeout.
+
+DEFAULT_TIMEOUT = 60 * 60 * 6 # 6 hours
+
+lib_send = requests.Session.send
+
+def send(*args, **kwargs):
+    if kwargs.get("timeout", None) is None:
+        kwargs["timeout"] = DEFAULT_TIMEOUT
+
+    return lib_send(*args, **kwargs)
+
+setattr(requests.Session, "send", send)
diff --git a/estuary-cdk/estuary_cdk/shim_airbyte_cdk.py b/estuary-cdk/estuary_cdk/shim_airbyte_cdk.py
index d902c2e9c9..ef0fcdf718 100644
--- a/estuary-cdk/estuary_cdk/shim_airbyte_cdk.py
+++ b/estuary-cdk/estuary_cdk/shim_airbyte_cdk.py
@@ -352,7 +352,7 @@ async def _run(
             await asyncio.sleep(0)
 
             if task.stopping.event.is_set():
-                task.log.debug(f"Airbyte shim is yielding to stop.")
+                task.log.info(f"Airbyte shim is yielding to stop.")
                 return
 
             if record := message.record:
@@ -449,5 +449,6 @@ async def _run(
                 raise RuntimeError("unexpected AirbyteMessage", message)
 
         # Emit a final checkpoint before exiting.
+        task.log.info("Emitting final checkpoint for sweep.")
         task.checkpoint(connector_state, merge_patch=False)
         return None
diff --git a/source-airtable/source_airtable/__main__.py b/source-airtable/source_airtable/__main__.py
index d5bdb20c5c..a3fc0ff8bb 100644
--- a/source-airtable/source_airtable/__main__.py
+++ b/source-airtable/source_airtable/__main__.py
@@ -1,4 +1,5 @@
 import estuary_cdk.pydantic_polyfill  # Must be first.
+import estuary_cdk.requests_session_send_patch # Must be second.
 
 import asyncio
 from estuary_cdk import shim_airbyte_cdk, flow
diff --git a/source-asana/source_asana/__main__.py b/source-asana/source_asana/__main__.py
index f40486290f..892b0bd90e 100644
--- a/source-asana/source_asana/__main__.py
+++ b/source-asana/source_asana/__main__.py
@@ -1,4 +1,5 @@
 import estuary_cdk.pydantic_polyfill  # Must be first.
+import estuary_cdk.requests_session_send_patch # Must be second.
 
 import asyncio
 from estuary_cdk import shim_airbyte_cdk, flow
diff --git a/source-brevo/source_brevo/__main__.py b/source-brevo/source_brevo/__main__.py
index 364b551c66..cea31f646a 100644
--- a/source-brevo/source_brevo/__main__.py
+++ b/source-brevo/source_brevo/__main__.py
@@ -1,4 +1,5 @@
 import estuary_cdk.pydantic_polyfill # Must be first.
+import estuary_cdk.requests_session_send_patch # Must be second.
 
 import asyncio
 
diff --git a/source-facebook-marketing/source_facebook_marketing/__main__.py b/source-facebook-marketing/source_facebook_marketing/__main__.py
index 4947caebe0..2178251662 100644
--- a/source-facebook-marketing/source_facebook_marketing/__main__.py
+++ b/source-facebook-marketing/source_facebook_marketing/__main__.py
@@ -1,4 +1,5 @@
 import estuary_cdk.pydantic_polyfill  # Must be first.
+import estuary_cdk.requests_session_send_patch # Must be second.
 
 import asyncio
 from estuary_cdk import shim_airbyte_cdk, flow
diff --git a/source-google-ads/source_google_ads/__main__.py b/source-google-ads/source_google_ads/__main__.py
index ae2741e73f..1b7ac3dcfc 100644
--- a/source-google-ads/source_google_ads/__main__.py
+++ b/source-google-ads/source_google_ads/__main__.py
@@ -1,4 +1,5 @@
 import estuary_cdk.pydantic_polyfill  # Must be first.
+import estuary_cdk.requests_session_send_patch # Must be second.
 
 import asyncio
 from estuary_cdk import shim_airbyte_cdk, flow
diff --git a/source-hubspot/source_hubspot/__main__.py b/source-hubspot/source_hubspot/__main__.py
index e800bdb77d..33d63798b4 100644
--- a/source-hubspot/source_hubspot/__main__.py
+++ b/source-hubspot/source_hubspot/__main__.py
@@ -1,4 +1,5 @@
 import estuary_cdk.pydantic_polyfill  # Must be first.
+import estuary_cdk.requests_session_send_patch # Must be second.
 
 import asyncio
 import urllib
diff --git a/source-iterable/source_iterable/__main__.py b/source-iterable/source_iterable/__main__.py
index e7959592dc..81a7c17160 100644
--- a/source-iterable/source_iterable/__main__.py
+++ b/source-iterable/source_iterable/__main__.py
@@ -1,4 +1,5 @@
 import estuary_cdk.pydantic_polyfill  # Must be first.
+import estuary_cdk.requests_session_send_patch # Must be second.
 
 import asyncio
 import urllib
diff --git a/source-jira-native/source_jira_native/__main__.py b/source-jira-native/source_jira_native/__main__.py
index 0e206e15ba..a1feada166 100644
--- a/source-jira-native/source_jira_native/__main__.py
+++ b/source-jira-native/source_jira_native/__main__.py
@@ -1,4 +1,5 @@
 import estuary_cdk.pydantic_polyfill  # Must be first.
+import estuary_cdk.requests_session_send_patch # Must be second.
 
 import asyncio
 import urllib
diff --git a/source-klaviyo/source_klaviyo/__main__.py b/source-klaviyo/source_klaviyo/__main__.py
index 09f128ae36..99fe4b1483 100644
--- a/source-klaviyo/source_klaviyo/__main__.py
+++ b/source-klaviyo/source_klaviyo/__main__.py
@@ -1,4 +1,5 @@
 import estuary_cdk.pydantic_polyfill  # Must be first.
+import estuary_cdk.requests_session_send_patch # Must be second.
 
 import asyncio
 import urllib
diff --git a/source-linkedin-ads-v2/source_linkedin_ads_v2/__main__.py b/source-linkedin-ads-v2/source_linkedin_ads_v2/__main__.py
index f230784673..562f8ae77d 100644
--- a/source-linkedin-ads-v2/source_linkedin_ads_v2/__main__.py
+++ b/source-linkedin-ads-v2/source_linkedin_ads_v2/__main__.py
@@ -1,4 +1,5 @@
 import estuary_cdk.pydantic_polyfill  # Must be first.
+import estuary_cdk.requests_session_send_patch # Must be second.
 
 import asyncio
 import urllib
diff --git a/source-linkedin-pages/source_linkedin_pages/__main__.py b/source-linkedin-pages/source_linkedin_pages/__main__.py
index 6d0bc61f86..3f5d26fa62 100644
--- a/source-linkedin-pages/source_linkedin_pages/__main__.py
+++ b/source-linkedin-pages/source_linkedin_pages/__main__.py
@@ -1,4 +1,5 @@
 import estuary_cdk.pydantic_polyfill  # Must be first. # noqa
+import estuary_cdk.requests_session_send_patch # Must be second.
 
 import asyncio
 from estuary_cdk import shim_airbyte_cdk, flow
diff --git a/source-mixpanel-native/source_mixpanel_native/__main__.py b/source-mixpanel-native/source_mixpanel_native/__main__.py
index 452dda612c..ab12c184ad 100644
--- a/source-mixpanel-native/source_mixpanel_native/__main__.py
+++ b/source-mixpanel-native/source_mixpanel_native/__main__.py
@@ -1,4 +1,5 @@
 import estuary_cdk.pydantic_polyfill  # Must be first.
+import estuary_cdk.requests_session_send_patch # Must be second.
 
 import asyncio
 import urllib
diff --git a/source-recharge/source_recharge/__main__.py b/source-recharge/source_recharge/__main__.py
index 9f6a1b89c1..f5189e4355 100644
--- a/source-recharge/source_recharge/__main__.py
+++ b/source-recharge/source_recharge/__main__.py
@@ -1,4 +1,5 @@
 import estuary_cdk.pydantic_polyfill  # Must be first.
+import estuary_cdk.requests_session_send_patch # Must be second.
 
 import asyncio
 import urllib
diff --git a/source-twilio/source_twilio/__main__.py b/source-twilio/source_twilio/__main__.py
index 7dfdae9c17..a6d64c6ea8 100644
--- a/source-twilio/source_twilio/__main__.py
+++ b/source-twilio/source_twilio/__main__.py
@@ -1,4 +1,5 @@
 import estuary_cdk.pydantic_polyfill  # Must be first.
+import estuary_cdk.requests_session_send_patch # Must be second.
 
 import asyncio
 import urllib
diff --git a/source-zendesk-support/source_zendesk_support/__main__.py b/source-zendesk-support/source_zendesk_support/__main__.py
index f44a639ff6..6ac265fb2d 100644
--- a/source-zendesk-support/source_zendesk_support/__main__.py
+++ b/source-zendesk-support/source_zendesk_support/__main__.py
@@ -1,4 +1,5 @@
 import estuary_cdk.pydantic_polyfill # Must be first.
+import estuary_cdk.requests_session_send_patch # Must be second.
 
 import asyncio
 import json