diff --git a/.cirrus.yml b/.cirrus.yml
index 727a73f37f35e..a352406e2b932 100644
--- a/.cirrus.yml
+++ b/.cirrus.yml
@@ -135,7 +135,8 @@ task:
   ##   - rm /tmp/.com.apple.dt.CommandLineTools.installondemand.in-progress
   ##
   brew_valgrind_pre_script:
-    - brew update
+    # Retry a few times because this tends to fail randomly.
+    - for i in {1..5}; do brew update && break || sleep 15; done
     - brew config
     - brew tap LouisBrunner/valgrind
     # Fetch valgrind source but don't build it yet.