diff --git a/docker-compose.yml b/docker-compose.yml
index 8d86a21bc80..595944707b6 100644
--- a/docker-compose.yml
+++ b/docker-compose.yml
@@ -161,7 +161,7 @@ services:
   postgres:
     <<: *restart_policy
     # Using the same postgres version as Sentry dev for consistency purposes
-    image: "postgres:14.24-bookworm"
+    image: "postgres:14.24-trixie"
     healthcheck:
       <<: *healthcheck_defaults
       # Using default user "postgres" from sentry/sentry.conf.example.py or value of POSTGRES_USER if provided
diff --git a/install.sh b/install.sh
index 3b4d9b50011..9bbe33f10b0 100755
--- a/install.sh
+++ b/install.sh
@@ -38,9 +38,9 @@ source install/ensure-relay-credentials.sh
 source install/generate-secret-key.sh
 source install/build-docker-images.sh
 source install/migrate-seaweedfs-kek.sh
+source install/upgrade-postgres.sh
 source install/bootstrap-s3-nodestore.sh
 source install/bootstrap-snuba.sh
-source install/upgrade-postgres.sh
 source install/ensure-correct-permissions-profiles-dir.sh
 source install/bootstrap-s3-profiles.sh
 source install/set-up-and-migrate-database.sh
diff --git a/install/upgrade-postgres.sh b/install/upgrade-postgres.sh
index 6785ae879ea..7c0b00b5963 100644
--- a/install/upgrade-postgres.sh
+++ b/install/upgrade-postgres.sh
@@ -1,5 +1,7 @@
 echo "${_group}Ensuring proper PostgreSQL version ..."
 
+postgres_version=$($CONTAINER_ENGINE run --rm -v sentry-postgres:/db busybox sh -c 'if [ -f /db/PG_VERSION ]; then cat /db/PG_VERSION; fi')
+
 if [[ -n "$($CONTAINER_ENGINE volume ls -q --filter name=sentry-postgres)" && "$($CONTAINER_ENGINE run --rm -v sentry-postgres:/db busybox cat /db/PG_VERSION 2>/dev/null)" == "9.6" ]]; then
   $CONTAINER_ENGINE volume rm sentry-postgres-new || true
   # If this is Postgres 9.6 data, start upgrading it to 14.0 in a new volume
@@ -41,4 +43,16 @@ if [[ -n "$($CONTAINER_ENGINE volume ls -q --filter name=sentry-postgres)" && "$
   $dc stop postgres
 fi
 
+# Reindex existing PostgreSQL 14 data once for the glibc 2.36 (Bookworm) -> 2.41 (Trixie) change.
+if [[ "$postgres_version" == "14" || -z "$postgres_version" ]]; then
+  needs_reindex=$($CONTAINER_ENGINE run --rm -v sentry-postgres:/db busybox sh -c 'if [ -f /db/PG_VERSION ] && [ ! -f /db/14-trixie-reindexed ]; then echo yes; fi')
+
+  start_service_and_wait_ready postgres
+  if [[ "$needs_reindex" == "yes" ]]; then
+    echo "Re-indexing due to glibc change, this may take a while..."
+    $dc exec postgres psql -U postgres -v ON_ERROR_STOP=1 -c "REINDEX DATABASE postgres;"
+  fi
+  $dc exec postgres sh -c 'touch "$PGDATA/14-trixie-reindexed"'
+fi
+
 echo "${_endgroup}"