Outlook 2019 won't activate Timeslips add-in

I have Timeslips Premium and Outlook 2019 set up on a new Dell laptop (Windows 10).  After completing our billing, Timeslips showed invoices having been sent via email.  Outlook, however didn't send them. Looking at the Add-In Options page in Outlook, the Timeslips Add-in was shown as Inactive.  I went to the Manage Add-ins page.  Timeslips Add-In for Outlook was shown as an available add-in, but when i checked the box to activate it, closed Outlook and then restarted it, the add-in again was shown as Inactive. 

When i highlighted the Timeslips add-in, its file location (shown below the available add-ins box) was blank.  I tried clicking the Add button, navigating to the Timeslips add-in application file in Program Files (...\Timeslips\TSOLAdllIn.dll) and clicking that to add, but Outlook said it wasn't a valid Office Add-in. 

Not sure what to try next. Any suggestions for a solution would be appreciated.

  • The Timeslips Add in for Outlook does not handle email of the bills. You will generally not see the emails in Outlook unless you copy yourself. As long as you have 32 bit version of Outlook and only one email account in the Outlook profile they usually go without an issue, but I recommend cc yourself to be certain. 

  • That must be a new feature with Outlook 2019.  The emailed invoices were always shown in my Sent Items folder when I used Outlook 2016.  I'll try cc-ing myself. Thanks for your help!

  • You should still see them in your Sent folder.  Make sure your IT folks loaded the 32-bit version of Microsoft Office.  Timeslips does not work with the 64-bit (which is now the default for Microsoft).

    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.
    404-325-9779
    [email protected]

  • Also, just so you know, the add-in is not necessary if you just want to email bills.  Emailing is a totally different function than the add-in.

    The add-in lets you: sync contacts with TImeslips clients, and creating slips from Outlook items. The VAST majority of Timeslips users do not do this, so no need to chase down the add-in functionality if you only need the emailing bills functionality.

    32-bit still the only supported version on that though.

    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.
    404-325-9779
    [email protected]

  • I uninstalled the 64-bit version and installed the 32-bit.  The email feature works great now! Thank you so much for your help in this matter!