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Troubleshooting Common Issues

If you're experiencing issues with Yesware, start by checking the Yesware status page — subscribe to updates to stay on top of any ongoing incidents.

If there's no status to explain your issue, the steps below resolve the majority of problems for both Gmail and Outlook users.

Gmail (Chrome)​

Work through these steps in order:

  1. Update Chrome — Go to chrome://settings/help and confirm you're on the latest version. If prompted to relaunch, do so.
  2. Uninstall Yesware — Go to chrome://extensions, click Remove next to Yesware, and refresh Gmail.
  3. Clear cache — Go to chrome://settings/clearBrowserData, switch to the Advanced tab, set Time Range to All Time, check Cookies, Cached images, and Hosted app data, then click Clear Data.
  4. Clear local storage — Go to Chrome menu > More Tools > Developer Tools > Console, type localStorage.clear() next to the > symbol, press Enter, then close the pane and refresh Gmail.
  5. Reinstall Yesware — Download and reinstall from yesware.com/install.
  6. Restart Chrome — Close Chrome completely, reopen it, and sign back into Gmail.

Outlook​

  1. Update Outlook — Make sure you're running the latest version
  2. Check the sidebar is pinned — In compose windows, confirm the Yesware sidebar is open and pinned
  3. Remove and reinstall the add-in — Click Get Add-ins in Outlook, go to My Add-ins, remove Yesware, then re-add it
  4. Check your Outlook version — Some features require Outlook Version 2008 (Build 13127.21064) or above

Authentication Issues​

Outlook sidebar is asking me to log in when sending a tracked email​

This usually happens when authentication between your email and Yesware has broken. To fix it:

  1. Open Chrome and go to Outlook.com
  2. Sign in to your account
  3. Click into an email in your inbox and select More Actions
  4. Select Yesware > Open Yesware and log in when prompted

Once logged in through Outlook Web, close and reopen your Outlook desktop app — you should be authenticated automatically.

If the issue persists, contact support@yesware.com.

When to Contact Support​

Reach out to support@yesware.com if:

  • Basic troubleshooting steps don't resolve the issue
  • You're seeing a persistent error message
  • Features stopped working unexpectedly after working before
  • You need help with account-specific configuration

When contacting support, include: a description of the issue, steps you've already tried, your email client (Gmail or Outlook), your Outlook version if applicable, and any screenshots or error messages.