diff --git a/bin/flutter b/bin/flutter
index f5c4da1392..e7cf407ba8 100755
--- a/bin/flutter
+++ b/bin/flutter
@@ -39,6 +39,23 @@ function _rmlock () {
   [ -n "$FLUTTER_UPGRADE_LOCK" ] && rm -f "$FLUTTER_UPGRADE_LOCK"
 }
 
+function retry_upgrade {
+  local total_tries="10"
+  local remaining_tries=$(($total_tries - 1))
+  while [[ "$remaining_tries" > 0 ]]; do
+    (cd "$FLUTTER_TOOLS_DIR" && "$PUB" upgrade "$VERBOSITY" --no-packages-dir) && break
+    echo "Error: Unable to 'pub upgrade' flutter tool. Retrying in five seconds... ($remaining_tries tries left)"
+    remaining_tries=$(($remaining_tries - 1))
+    sleep 5
+  done
+
+  if [[ "$remaining_tries" == 0 ]]; then
+    echo "Command 'pub upgrade' still failed after $total_tries tries, giving up."
+    return 1
+  fi
+  return 0
+}
+
 function upgrade_flutter () {
   mkdir -p "$FLUTTER_ROOT/bin/cache"
 
@@ -94,7 +111,7 @@ function upgrade_flutter () {
     echo Building flutter tool...
     if [[ "$CI" == "true" || "$BOT" == "true" || "$CONTINUOUS_INTEGRATION" == "true" || "$CHROME_HEADLESS" == "1" ]]; then
       PUB_ENVIRONMENT="$PUB_ENVIRONMENT:flutter_bot"
-      VERBOSITY="--verbosity=all"
+      VERBOSITY="--verbosity=normal"
     fi
     export PUB_ENVIRONMENT="$PUB_ENVIRONMENT:flutter_install"
 
@@ -102,12 +119,8 @@ function upgrade_flutter () {
       export PUB_CACHE="${PUB_CACHE:-"$FLUTTER_ROOT/.pub-cache"}"
     fi
 
-    while : ; do
-      cd "$FLUTTER_TOOLS_DIR"
-      "$PUB" upgrade "$VERBOSITY" --no-packages-dir && break
-      echo "Error: Unable to 'pub upgrade' flutter tool. Retrying in five seconds..."
-      sleep 5
-    done
+    retry_upgrade
+
     "$DART" --snapshot="$SNAPSHOT_PATH" --packages="$FLUTTER_TOOLS_DIR/.packages" "$SCRIPT_PATH"
     echo "$revision" > "$STAMP_PATH"
   fi
diff --git a/bin/flutter.bat b/bin/flutter.bat
index fd458cfba7..43af48be67 100644
--- a/bin/flutter.bat
+++ b/bin/flutter.bat
@@ -126,29 +126,38 @@ GOTO :after_subroutine
       GOTO not_on_bot
       :on_bot
         SET PUB_ENVIRONMENT=%PUB_ENVIRONMENT%:flutter_bot
-        SET VERBOSITY=--verbosity=all
+        SET VERBOSITY=--verbosity=normal
       :not_on_bot
       SET PUB_ENVIRONMENT=%PUB_ENVIRONMENT%:flutter_install
       IF "%PUB_CACHE%" == "" (
         IF EXIST "%pub_cache_path%" SET PUB_CACHE=%pub_cache_path%
       )
+
+      SET /A total_tries=10
+      SET /A remaining_tries=%total_tries%-1
       :retry_pub_upgrade
-      CALL "%pub%" upgrade "%VERBOSITY%" --no-packages-dir
-      IF "%ERRORLEVEL%" NEQ "0" (
-        ECHO Error: Unable to 'pub upgrade' flutter tool. Retrying in five seconds...
-        timeout /t 5 /nobreak
+        ECHO Running pub upgrade...
+        CALL "%pub%" upgrade "%VERBOSITY%" --no-packages-dir
+        IF "%ERRORLEVEL%" EQU "0" goto :upgrade_succeeded
+        ECHO Error Unable to 'pub upgrade' flutter tool. Retrying in five seconds... (%remaining_tries% tries left)
+        timeout /t 5 /nobreak 2>NUL
+        SET /A remaining_tries-=1
+        IF "%remaining_tries%" EQU "0" GOTO upgrade_retries_exhausted
         GOTO :retry_pub_upgrade
-      )
+      :upgrade_retries_exhausted
+        SET exit_code=%ERRORLEVEL%
+        ECHO Error: 'pub upgrade' still failing after %total_tries% tries, giving up.
+        GOTO final_exit
+      :upgrade_succeeded
     ENDLOCAL
 
     POPD
 
-    :retry_dart_snapshot
     CALL "%dart%" --snapshot="%snapshot_path%" --packages="%flutter_tools_dir%\.packages" "%script_path%"
     IF "%ERRORLEVEL%" NEQ "0" (
-      ECHO Error: Unable to create dart snapshot for flutter tool. Retrying...
-      timeout /t 5 /nobreak
-      GOTO :retry_dart_snapshot
+      ECHO Error: Unable to create dart snapshot for flutter tool.
+      SET exit_code=%ERRORLEVEL%
+      GOTO :final_exit
     )
     >"%stamp_path%" ECHO %revision%
 
@@ -172,4 +181,5 @@ IF "%exit_code%" EQU "253" (
   SET exit_code=%ERRORLEVEL%
 )
 
+:final_exit
 EXIT /B %exit_code%
diff --git a/dev/bots/cirrus_setup.sh b/dev/bots/cirrus_setup.sh
index f7c292023a..451bcbc281 100755
--- a/dev/bots/cirrus_setup.sh
+++ b/dev/bots/cirrus_setup.sh
@@ -1,28 +1,15 @@
 #!/bin/bash
 set -e
 
+function error() {
+  echo "$@" 1>&2
+}
+
 # This script is only meant to be run by the Cirrus CI system, not locally.
 # It must be run from the root of the Flutter repo.
 
-# Collects log output in a tmpfile, but only prints it if the command fails.
-function log_on_fail() {
-  local COMMAND="$@"
-  local TMPDIR="$(mktemp -d)"
-  local TMPFILE="$TMPDIR/command.log"
-  local EXIT=0
-  if ("$@" > "$TMPFILE" 2>&1); then
-    echo "'$COMMAND' succeeded."
-  else
-    EXIT=$?
-    cat "$TMPFILE" 1>&2
-    echo "FAIL: '$COMMAND' exited with code $EXIT" 1>&2
-  fi
-  rm -rf "$TMPDIR"
-  return "$EXIT"
-}
-
 function accept_android_licenses() {
-  yes "y" | flutter doctor --android-licenses
+  yes "y" | flutter doctor --android-licenses > /dev/null 2>&1
 }
 
 echo "Flutter SDK directory is: $PWD"
@@ -30,14 +17,15 @@ echo "Flutter SDK directory is: $PWD"
 # Run flutter to download dependencies and precompile things, and to disable
 # analytics on the bots.
 echo "Downloading build dependencies and pre-compiling Flutter snapshot"
-log_on_fail ./bin/flutter config --no-analytics
+./bin/flutter config --no-analytics
 
 # Run doctor, to print it to the log for debugging purposes.
 ./bin/flutter doctor -v
 
 # Accept licenses.
-log_on_fail accept_android_licenses && echo "Android licenses accepted."
+echo "Accepting Android licenses."
+accept_android_licenses || (error "Accepting Android licenses failed." && false)
 
 # Run pub get in all the repo packages.
 echo "Updating packages for Flutter."
-log_on_fail ./bin/flutter update-packages
+./bin/flutter update-packages
diff --git a/dev/bots/test.dart b/dev/bots/test.dart
index b29bebaf1c..942dfdbdf2 100644
--- a/dev/bots/test.dart
+++ b/dev/bots/test.dart
@@ -134,7 +134,7 @@ Future<Null> _checkForTrailingSpaces() async {
       'git', <String>['diff', '-U0', '--no-color', '--name-only', commitRange, '--'] + fileTypes,
       workingDirectory: flutterRoot,
     );
-    if (changedFilesResult.stdout == null) {
+    if (changedFilesResult.stdout == null || changedFilesResult.stdout.trim().isEmpty) {
       print('No files found that need to be checked for trailing whitespace.');
       return;
     }