Sounds like you are checking all the right things, so kudos for your efforts so far.  However, it sounds like Timeslips is not finding what it needs when it goes to talk to Outlook. 

Any chance of refreshing/update to Outlook?  Sounds like the Outlook installation is not registered correctly, because of the message when trying to enable the Outlook link.

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 repaired Outlook and no joy there.  So, I uninstalled and reinstalled Outlook, and that fixed whatever was broken.  My bills are happily emailing their way through the ether as I type this.  I don’t know if it was because Outlook was preinstalled or what.  Regardless, it works now.

Excellent! Good work Phil! Glad to hear you got it firing. Sounds like a registry entry wasn't where Timeslips was expecting to find it. The reinstall fixed it.

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] 

This is the closest forum for my problem that I could find.  I have a client for whom the bills are no longer sending - I am running Timeslips 2019 and sending emails out over Outlook 2016.  I've been using these two programs for the past ten years, but for some reason, since I downloaded TS2019, the emails to this particular client no longer go through.  When I look at the log, it says the email address is ambiguous.

That error is more of an Outlook error than a Timeslips error. I would search the Outlook forums for "email address is ambiguous."

See here as an example: https://searchwindowsserver.techtarget.com/tip/Working-through-ambiguous-e-mail-addresses

Or here: https://support.microsoft.com/en-us/help/2786433/5-1-4-resolver-adr-ambiguous-ambiguous-address-error-message-when-you

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]