diff --git a/script/sentry_upload_dif.sh b/script/sentry_upload_dif.sh
index b9bc5786db6..80e4b69b622 100755
--- a/script/sentry_upload_dif.sh
+++ b/script/sentry_upload_dif.sh
@@ -8,11 +8,37 @@
 
 set -x
 
-if which sentry-cli >/dev/null; then
-  ERROR="$(sentry-cli upload-dif "$DEBUG_FILE_OR_FOLDER_PATH")"
-  if [ ! $? -eq 0 ]; then
-    echo "warning: sentry-cli - $ERROR"
-  fi
-else
-  echo "warning: sentry-cli not installed, download from https://github.com/getsentry/sentry-cli/releases"
+MAX_ATTEMPTS=3
+INITIAL_RETRY_DELAY_SECONDS=5
+MAX_RETRY_DELAY_SECONDS=10
+
+if ! command -v sentry-cli >/dev/null; then
+  echo "::error title=Error uploading Sentry debug files::sentry-cli not installed, download from https://github.com/getsentry/sentry-cli/releases"
+  exit 1
 fi
+
+if [ ! -e "$DEBUG_FILE_OR_FOLDER_PATH" ]; then
+  echo "::error title=Error uploading Sentry debug files::DEBUG_FILE_OR_FOLDER_PATH '$DEBUG_FILE_OR_FOLDER_PATH' does not exist"
+  exit 1
+fi
+
+attempt=1
+retry_delay_seconds=$INITIAL_RETRY_DELAY_SECONDS
+while true; do
+  if sentry-cli upload-dif "$DEBUG_FILE_OR_FOLDER_PATH"; then
+    echo "Sentry debug file upload succeeded on attempt $attempt/$MAX_ATTEMPTS."
+    exit 0
+  fi
+
+  if [ "$attempt" -ge "$MAX_ATTEMPTS" ]; then
+    echo "::error title=Error uploading Sentry debug files::sentry-cli upload-dif failed after $MAX_ATTEMPTS attempts"
+    exit 1
+  fi
+  echo "::warning title=Sentry debug file upload failed::Attempt $attempt/$MAX_ATTEMPTS failed; retrying in ${retry_delay_seconds}s"
+  sleep "$retry_delay_seconds"
+  attempt=$((attempt + 1))
+  retry_delay_seconds=$((retry_delay_seconds * 2))
+  if [ "$retry_delay_seconds" -gt "$MAX_RETRY_DELAY_SECONDS" ]; then
+    retry_delay_seconds=$MAX_RETRY_DELAY_SECONDS
+  fi
+done