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Emailing Bills Error: “The recipient's address is not valid” and Other Email Issues After Windows Update (Known Issue)

Sophia Harvey
Posted By

We are currently seeing a known issue affecting some users when emailing bills, including errors such as:
“Failure: The recipient's address is not valid.”

The issue persists even when using both 32-bit and 64-bit versions of Outlook, which are not functioning as expected in this scenario.

After further investigation, this is not caused by Timeslips. We have identified a recent Microsoft Windows update as the likely source. Specifically, the April 2026 Windows 11 (version 25H2) update (build 26100.8247) has introduced a known issue impacting email functionality in third-party applications such as Outlook Classic, backup tools, and CRM systems. This appears to be related to a regression in the Windows networking stack and MAPI layer.

Additionally, rolling back the Windows update does not appear to reverse the impact it has already had on Microsoft Outlook functionality.

At this time, this issue is outside the scope of Timeslips support. We recommend contacting Microsoft Support for assistance or monitoring Microsoft’s official updates for a resolution. Please chck back for updates.

We will share any new information here as it is received.

D’Wan Sophia Harvey

Senior Technical Support Specialist

 Sage.com | Twitter | Instagram | Facebook | YouTube | LinkedIn | Community

     

"Success is not just about what you accomplish in your life; it’s about what you inspire others to do."

      – Anonymous

  • Oooh, good to know, but really bad timing with billing coming up. Best of luck.

    Nancy Duhon, Esq.
    Duhon Technology Solutions, LLC
    Master Certified Consultant for Sage Timeslips
    Providing individual Consultations and Third Party Remote Desktop Support - including older/unsupported versions.
    Co-Author of "The E-Billing Process Using Sage Timeslips©" available here: www.certifiedresourcesnetwork.com/
    LawPay Partnered Consultant
    MyCase Consultant
    404-325-9779
    [email protected]

  • My Outlook add-in just stopped working, however, I believe the circumstances are different.  This workstation is running Windows 10 and would not have received that Windows 11 update.

    The "Timeslips add-in for Outlook" entry was still showing in the Com Add-ins in Outlook but the "Location" entry is now blank.  It thus cannot load the add-in.  

    Is there any way to readd that entry?  I have been unable to locate the correct Office add-in to put it back.

    Any help would be appreciated.

  • in reply to Gary Drost

    The Timeslips add in for Outlook has nothing to do with emailing your bills. It’s an add-on that allows you to create a time entry in Outlook.  It is not heavily used. Therefore, I would say that that is not the issue

  • I found that if a client as multiple Outlook email accounts setup that is the source of the issue.  I had my client remove all email Outlook addresses except they one that is used to send bills, sent the bills and readded the other email accounts to Outlook.  until the issue is resolved, this is hte only workround that i am aware of

  • in reply to cbarnes

    That is fabulous.  I just had my client do the same thing and the bills sent out with no issue!

  • I have a client on an older version of TS AND on Windows 10 experiencing the same error.  I told him he needs to send bills manually or update his computer.  There must have been an update from Microsoft to Windows 10 also.  His system shows updates on 4.15.26.

  • I am currently running Timeslips Premium Pro, & Outlook 64-bit.

    As of the other day, I can't email bills to our clients anymore. Email log reads: "Failure: Unknown Error".

    I've already tried MAPI and don't have any IT support. 

    Is there a way to fix this without uninstalling and re-installing Outlook? I received a reply saying to install the new version of Timeslips Premium but there are a few options (install add-ons only? install entire version?) & although I'd really like to speak with a person from Sage on the phone to guide me, it seems that's not a possibility. 

    If I must install this new version to rectify this matter, do I install the entire update? Will my database remain intact? Should I make a mirror image or backup of my computer prior to doing this???? I work for a solo practitioner and am the only employee here. 

    Any guidance is appreciated. Thanks.

  • in reply to Mel61

     Thanks for the additional info. Your situation is different that I at first thought.

    I don't really think there is much you can do just right now. I don't think reinstalling anything will help, because it was a Windows update that caused the issue. Nothing in Timeslips changed. 

    You are caught in the middle between Microsoft and Sage. As you can see from the previous post by my colleague  she has had some success with Outlook Profiles that have only a single email account in them. If you decide to go that route, I would just create a second profile with the single account in it and not deal with deleting and re-entering the accounts into your default profile. Then just launch Outlook with that single account profile when you want to approve and email the bills.

    As  mentioned nothing is keeping you from printing your Timeslips bill to PDF and manually attaching it to an email and sending it out. It is just that once you have that bit automated, it feels so wrong to have to go back and do it manually. Tired face If you would like some assistance is minimizing the steps to doing that, I'd be happy to help with that.

    Watch this thread for updates as to when/if we get another update to Windows that fixes the issue. The 'good' news is that this is not an isolated issue to Timeslips. Other programs that use the MAPI link were also affected, so Microsoft should be sufficiently incentivized to fix it quickly.

    Nancy Duhon, Esq.
    Duhon Technology Solutions, LLC
    Master Certified Consultant for Sage Timeslips
    Providing individual Consultations and Third Party Remote Desktop Support - including older/unsupported versions.
    Co-Author of "The E-Billing Process Using Sage Timeslips©" available here: www.certifiedresourcesnetwork.com/
    LawPay Partnered Consultant
    MyCase Consultant
    404-325-9779
    [email protected]

  • in reply to Nancy Duhon

    i found that if a user had multiple Outlook accounts and deleted all but one of them, the emailing bills error goes away.

  • Hello Everyone,

    We want to provide an update regarding the recent Outlook email functionality issue that may have impacted some Sage Timeslips users, particularly when sending emails (such as bills or statements) through Outlook.

    Current Status

    Microsoft has released an update that resolves this issue for many affected users.

    Fix Details

    • Version: 2604
    • Build: 19929.20172

    Customers with automatic updates enabled should receive the fix by simply closing and reopening Outlook.

    What Timeslips Users Should Do

    If you or your clients are still experiencing issues when sending emails from Timeslips via Outlook:

    1. Verify the installed Microsoft Office version/build
    2. Update to Version 2604 (or later)
    3. Restart Outlook before testing email functionality again in Timeslips

    If the issue persists after updating, continue standard troubleshooting and log a support case as needed.

    Important Notes

    • This issue primarily affects emails associated with multiple aliases
    • Some customers may have seen partial improvement from a previous Microsoft update
    • We are still seeing ongoing reports in certain cases

    Next Steps from Microsoft

    Microsoft has confirmed they have identified the root cause and are working on a more comprehensive fix, expected in:

    • Upcoming Version: 2605
    • Release Date: To be announced

    Additional Resources

    For more details, refer to Microsoft’s official release notes:
    learn.microsoft.com/.../current-channel

    We’re Here to Help

    Please continue to monitor for any remaining issues when sending emails from Timeslips. If problems persist after updating, escalate through the appropriate support channels so we can assist further.

    Thank you for your patience and for being part of the Sage Timeslips community.

    D’Wan Sophia Harvey

    Senior Technical Support Specialist

     Sage.com | Twitter | Instagram | Facebook | YouTube | LinkedIn | Community

         

    “Your impact on others will always outlast your achievements.”

    – Anonymous

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