diff --git a/source/common/http/conn_pool_grid.cc b/source/common/http/conn_pool_grid.cc
index ba51e7eee7e1..07b9bde9c618 100644
--- a/source/common/http/conn_pool_grid.cc
+++ b/source/common/http/conn_pool_grid.cc
@@ -191,6 +191,9 @@ void ConnectivityGrid::WrapperCallbacks::cancelAllPendingAttempts(
 
 absl::optional<ConnectivityGrid::StreamCreationResult>
 ConnectivityGrid::WrapperCallbacks::tryAnotherConnection() {
+  if (grid_.destroying_) {
+    return {};
+  }
   absl::optional<PoolIterator> next_pool = grid_.nextPool(current_);
   if (!next_pool.has_value()) {
     // If there are no other pools to try, return an empty optional.
@@ -236,10 +239,10 @@ ConnectivityGrid::ConnectivityGrid(
 ConnectivityGrid::~ConnectivityGrid() {
   // Ignore idle callbacks while the pools are destroyed below.
   destroying_ = true;
-  // Callbacks might have pending streams registered with the pools, so cancel and delete
-  // the callback before deleting the pools.
-  wrapped_callbacks_.clear();
+  // Make sure to clear the pools (which deletes all active connections, and
+  // signals callers) before deleting callbacks.
   pools_.clear();
+  wrapped_callbacks_.clear();
 }
 
 void ConnectivityGrid::deleteIsPending() {
diff --git a/tools/base/requirements.txt b/tools/base/requirements.txt
index 268f131abcaf..5848d26a062f 100644
--- a/tools/base/requirements.txt
+++ b/tools/base/requirements.txt
@@ -689,9 +689,9 @@ gitdb==4.0.11 \
     --hash=sha256:81a3407ddd2ee8df444cbacea00e2d038e40150acfa3001696fe0dcf1d3adfa4 \
     --hash=sha256:bf5421126136d6d0af55bc1e7c1af1c397a34f5b7bd79e776cd3e89785c2b04b
     # via gitpython
-gitpython==3.1.41 \
-    --hash=sha256:c36b6634d069b3f719610175020a9aed919421c87552185b085e04fbbdb10b7c \
-    --hash=sha256:ed66e624884f76df22c8e16066d567aaa5a37d5b5fa19db2c6df6f7156db9048
+gitpython==3.1.42 \
+    --hash=sha256:1bf9cd7c9e7255f77778ea54359e54ac22a72a5b51288c457c881057b7bb9ecd \
+    --hash=sha256:2d99869e0fef71a73cbd242528105af1d6c1b108c60dfabd994bf292f76c3ceb
     # via -r requirements.in
 google-apitools==0.5.32 \
     --hash=sha256:b78f74116558e0476e19501b5b4b2ac7c93261a69c5449c861ea95cbc853c688 \
@@ -700,7 +700,9 @@ google-apitools==0.5.32 \
 google-auth[aiohttp]==2.27.0 \
     --hash=sha256:8e4bad367015430ff253fe49d500fdc3396c1a434db5740828c728e45bcce245 \
     --hash=sha256:e863a56ccc2d8efa83df7a80272601e43487fa9a728a376205c86c26aaefa821
-    # via gsutil
+    # via
+    #   google-auth
+    #   gsutil
 google-reauth==0.1.1 \
     --hash=sha256:cb39074488d74c8853074dde47368bbf8f739d4a4338b89aab696c895b6d8368 \
     --hash=sha256:f9f6852a55c2c5453d581cd01f3d1278e86147c03d008409800390a834235892
@@ -1061,6 +1063,7 @@ pyjwt[crypto]==2.8.0 \
     # via
     #   gidgethub
     #   pygithub
+    #   pyjwt
 pylsqpack==0.3.18 \
     --hash=sha256:005ddce84bdcbf5c3cf99f764504208e1aa0a91a8331bf47108f2708f2a315e6 \
     --hash=sha256:06e1bbe47514b83cd03158e5558ef8cc44f578169c1820098be9f3cc4137f16a \