NOTE: If you are having problems with a Desktop version of Outlook (Outlook Classic on Windows, New Outlook on Windows, Outlook for Mac) you should also test the web version of Outlook to see if the issue is present or not.

This guide provides step-by-step troubleshooting instructions for diagnosing issues with the SendSafely Outlook Web Add-in. 

Step 1 - Verify the Add-in Version

Create a new email and open the SendSafely Add-in, make sure you are unauthenticated or the add-in is not functioning as expected:

• Locate the SendSafely Add-in for Outlook title in the Outlook sidebar.
• If you are not logged in, over your mouse over the title to display a tooltip (see below). and note the version number shown in the tooltip. 

• If you ARE logged in, hover over the "You are logged in as" section at the bottom of the sidebar app to reveal a tooltip with the version number.  

If the version shown is outdated or you suspect Outlook is loading a cached version of the add-in, clear the add-in cache using the steps for your Outlook client below.

Clearing Cache: Classic Outlook on Windows

1. Close Outlook completely.
2. Press Win + R to open the Run dialog, then type the following path and press Enter:

%LOCALAPPDATA%\Microsoft\Office\16.0\Wef\

3. Delete the contents of this folder. This removes cached add-in files.
4. Reopen Outlook and verify the add-in version has updated.

Clearing Cache: New Outlook on Windows

New Outlook on Windows is a web-based application that uses its own browser cache.

1. Open New Outlook and click the Settings gear icon in the top-right corner.
2. Navigate to General > Privacy and data.
3. Under Delete history, click the Delete button to clear cached data.
4. Close and reopen New Outlook, then verify the add-in version.

Clearing Cache: Outlook on Mac

1. Quit Outlook completely.
2. Open Finder, press Cmd + Shift + G, and navigate to the following path:

~/Library/Containers/com.microsoft.Outlook/Data/Library/Caches/

3. Delete the contents of this folder.
4. Reopen Outlook and verify the add-in version has updated.

Clearing Cache: Outlook on the Web (Browser)

When using Outlook on the web, the add-in is cached by the browser.

1. Open your browser’s settings and navigate to the option for clearing browsing data (e.g., in Chrome: Settings > Privacy and security > Delete browsing data).
2. Select Cached images and files (you can uncheck other options to preserve your browsing history and cookies).
3. Click Delete data.
4. Perform a hard refresh of the Outlook page by pressing Ctrl + Shift + R (Windows/Linux) or Cmd + Shift + R (Mac).
5. Open the add-in sidebar and verify the version has updated.

If the Version Still Has Not Updated

If clearing the cache does not resolve the issue and the add-in continues to show an outdated version, try signing out and back in:

Step 2: Check for Conflicting Add-ins

Other Outlook Web Add-ins may cause conflicts with the SendSafely add-in.

1. Navigate to your Outlook add-ins list:

• In Outlook on the web: Click the three-dot menu (...) or Get Add-ins button in the toolbar.
• In Outlook desktop: Go to File > Manage Add-ins or Home > Get Add-ins.

2. Compile a list of all installed and enabled add-ins.
3. Send this list to the SendSafely support team so we can check for known compatibility issues.

Step 3: Check for Firewall and Network Restrictions

If your organization uses a firewall, proxy server, or other network security tool that restricts outbound internet traffic, the SendSafely add-in may be unable to communicate with the SendSafely servers. This can result in failed file uploads, authentication errors, email send event, or the add-in not loading at all.

To resolve this:

1. Contact the SendSafely support team to request the current list of domains and IP addresses that need to be whitelisted.
2. Provide the whitelist to your network or IT administrator so they can update the firewall or proxy rules accordingly.
3. Once the domains have been whitelisted, restart Outlook and test the add-in again.

Note: The required domains may change over time, so always request the most up-to-date whitelist from the SendSafely support team rather than relying on a previously provided list.

Step 4: Inspect Network Traffic and Console Logs (Outlook Web / Mac / New Windows)

Ensure the add-in sidebar is open:

1. Right-click inside the SendSafely sidebar panel and select Inspect (or Inspect Element) to open the browser Developer Tools.
2. In the add-in, add a file and add a recipient as you normally would.
3. In Developer Tools, switch to the Network tab:

• Apply a filter using your SendSafely domain (e.g., <domain>.sendsafely.com) to isolate traffic going to SendSafely.
• Look for any requests with error status codes (4xx or 5xx) or failed requests highlighted in red.

4. Switch to the Console tab:

• Review for any error messages logged during the file upload or recipient addition.

5. If errors are found, take screenshots or export the logs and send them to the SendSafely support team.

Step 5: Capture On-Send Event Logs

If no errors were detected in Step 3:

1. In Developer Tools, clear both the Network tab and the Console tab to get a fresh view of the next set of requests and logs.
2. Keep the SendSafely domain filter applied in the Network tab.

Step 6: Trigger the Send Event and Capture Errors

1. Click Send on your email.
2. Immediately check Developer Tools:

• Network tab: Look for any new requests to your SendSafely domain that returned error status codes or failed entirely.
• Console tab: Look for any new error messages logged during the send event.

3. If any errors are present, take screenshots or export the Network and Console logs and send them to the SendSafely support team.

Step 7: Enable Runtime Logging for Classic Windows Outlook

Classic Windows Outlook uses a JavaScript-only runtime that does not have browser Developer Tools. To capture logs during the on-send event, you must enable runtime logging via the Windows Registry.

1. Open the Windows Registry Editor by typing regedit in the Start menu search and opening the application.
2. Navigate to the following registry key:

           HKEY_CURRENT_USER\SOFTWARE\Microsoft\Office\16.0\WEF\Developer\

Note: If the Developer key does not exist under HKEY_CURRENT_USER\SOFTWARE\Microsoft\Office\16.0\WEF\, right-click the WEF key, select New > Key, and name it Developer.

3. Inside the Developer key, add a new String Value (REG_SZ) named:

        RuntimeLogging

4. Set the value of RuntimeLogging to the full path of the log file you want logs written to, for example:

        C:\temp\outlook_addin_log.txt

Important: The directory you specify (e.g., C:\temp\) must already exist, and your user account must have write permissions to it.

5. Restart Outlook for the logging changes to take effect.
6. Reproduce the issue with the add-in. Logs will be written to the specified file.
7. Send the log file to the SendSafely support team for analysis.

Note: These runtime logs only capture activity during the on-send event. They will not include logs from the taskpane or other add-in interactions.

Contacting Support

When reaching out to the SendSafely support team, please include:

• The add-in version (from Step 1)
• A list of other installed add-ins (from Step 2)
• Any screenshots or exported logs from Developer Tools (from Steps 3–5)
• The runtime log file if using Classic Windows Outlook (from Step 6)
• Your Outlook client type (Web, Mac, New Windows, or Classic Windows)
• Your Outlook version number