Okay, so I am going to reply just to clarify some things a bit.

1) Timeslips is not completely incompatible with Office365 64-bit. That is a bit too broad a statement, and therefore possibly misleading to others who may read it later. What will not work with Office365 64-bit is the "automatic" emailing of bills. I.e., Timeslips will prepare the PDF attachment and email message, but then is unable to send it over to Outlook to be sent.  All other features of Timeslips that do not depend on Outlook work just fine. Slips, payments, bills, etc. But no, you cannot use the automatic email feature with a 64-bit version of Outlook.

It may surprise you, but not all users use that feature. 

2) I do not have any other solutions other than the suggestion to use the 32-bit version of Outlook.  That is the very first thing we try, and resolves it most of the time. If you are still having trouble, then something else is in play. Could be antivirus, antimalware, security not allowing the API with Outlook 32-bit to fire. But here's the thing. THERE IS NOTHING THAT WE CHANGE IN TIMESLIPS TO MAKE THE LINK WORK. It is always resolved outside of Timeslips, either by changing to the 32-bit, or tweaking permissions/security. Sometimes I've chased it for quite a while, and still not gotten it to work. Don't really know why, just know it got cost prohibitive to continue chasing.

One thing you can try is a new Outlook profile that uses a single gmail account. I had a client who's firm email would not work, but her gmail would. That told us that the issue was not with Timeslips or Outlook per se, but with that specific email account. 

Remember, Timeslips is sending a bunch of emails to Outlook for it to send/deliver. That behavior can sometimes look similar to behavior from a virus. bot or other bad actor. Outlook and your security software is trying to play defense against viruses and such, and may be over defending. Another thing to test is will it work with the antivirus off completely. If it works, then you know you need to fine tune the antivirus.

3) I am not attempting to diminish/discount anyone's frustration when it does not work. Yes, it is a huge PITA. Especially when it was working marvelously, and then now it isn't. I've had two of my clients ask me about this very issue this week. Both were resolved by moving to 32-bit. What happens is they upgrade their Outlook for whatever reason, and the default install of Outlook is 64-bit. So if you do nothing, you get 64-bit. Then it turns out not to work, and we have to take that out and put the 32-bit, but only AFTER the agony of finding out it doesn't work. Not a pleasant experience.

4) The advice to post/complain about it on Sage City was good advice, but there is a slightly BETTER place to voice your frustration.  This is not a new issue, so under the Ideas section of this bulletin board, there is a prior post from Whitney Hess about this dated 10/2/2019. Lesa Cooper , dbelcher, and anyone else having this problem, what you also want to do is go to that Ideas post, and both add comments to it and (most importantly) UPVOTE it. Right now it only has three votes (one of which is mine), so Sage does not see it as a serious problem. So, go  here: https://www.sagecity.com/us/sage_timeslips/i/general_product_suggestions/bill-emailing-on-outlook-64-bit

And then click the UP arrow to the left of the title to add your votes. Higher votes = more attention to the problem.

5) dbelcher while I do no deny that the change you made may have solved your issue, that setting is really for an entirely different purpose. It is when you want to synchronize Timeslips with your Outlook Contacts. Most folks do NOT want to do that, so I have never tried to turn it on for my clients. The only time I've ever fooled with it was when a client called and wanted me to turn it OFF, because it was driving him crazy. But it is possible that somehow activating that link gave permission for Timeslips to talk to your Outlook, and now the emails are a third party beneficiary to those permissions. Which is all fine if it is working for you. And it may work for Lesa Cooper as well. But is not something I have ever done to get it work. Just saying...

Hope this helps everyone.

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]

Okay, so I am going to reply just to clarify some things a bit.

1) Timeslips is not completely incompatible with Office365 64-bit. That is a bit too broad a statement, and therefore possibly misleading to others who may read it later. What will not work with Office365 64-bit is the "automatic" emailing of bills. I.e., Timeslips will prepare the PDF attachment and email message, but then is unable to send it over to Outlook to be sent.  All other features of Timeslips that do not depend on Outlook work just fine. Slips, payments, bills, etc. But no, you cannot use the automatic email feature with a 64-bit version of Outlook.

It may surprise you, but not all users use that feature. 

2) I do not have any other solutions other than the suggestion to use the 32-bit version of Outlook.  That is the very first thing we try, and resolves it most of the time. If you are still having trouble, then something else is in play. Could be antivirus, antimalware, security not allowing the API with Outlook 32-bit to fire. But here's the thing. THERE IS NOTHING THAT WE CHANGE IN TIMESLIPS TO MAKE THE LINK WORK. It is always resolved outside of Timeslips, either by changing to the 32-bit, or tweaking permissions/security. Sometimes I've chased it for quite a while, and still not gotten it to work. Don't really know why, just know it got cost prohibitive to continue chasing.

One thing you can try is a new Outlook profile that uses a single gmail account. I had a client who's firm email would not work, but her gmail would. That told us that the issue was not with Timeslips or Outlook per se, but with that specific email account. 

Remember, Timeslips is sending a bunch of emails to Outlook for it to send/deliver. That behavior can sometimes look similar to behavior from a virus. bot or other bad actor. Outlook and your security software is trying to play defense against viruses and such, and may be over defending. Another thing to test is will it work with the antivirus off completely. If it works, then you know you need to fine tune the antivirus.

3) I am not attempting to diminish/discount anyone's frustration when it does not work. Yes, it is a huge PITA. Especially when it was working marvelously, and then now it isn't. I've had two of my clients ask me about this very issue this week. Both were resolved by moving to 32-bit. What happens is they upgrade their Outlook for whatever reason, and the default install of Outlook is 64-bit. So if you do nothing, you get 64-bit. Then it turns out not to work, and we have to take that out and put the 32-bit, but only AFTER the agony of finding out it doesn't work. Not a pleasant experience.

4) The advice to post/complain about it on Sage City was good advice, but there is a slightly BETTER place to voice your frustration.  This is not a new issue, so under the Ideas section of this bulletin board, there is a prior post from Whitney Hess about this dated 10/2/2019. Lesa Cooper , dbelcher, and anyone else having this problem, what you also want to do is go to that Ideas post, and both add comments to it and (most importantly) UPVOTE it. Right now it only has three votes (one of which is mine), so Sage does not see it as a serious problem. So, go  here: https://www.sagecity.com/us/sage_timeslips/i/general_product_suggestions/bill-emailing-on-outlook-64-bit

And then click the UP arrow to the left of the title to add your votes. Higher votes = more attention to the problem.

5) dbelcher while I do no deny that the change you made may have solved your issue, that setting is really for an entirely different purpose. It is when you want to synchronize Timeslips with your Outlook Contacts. Most folks do NOT want to do that, so I have never tried to turn it on for my clients. The only time I've ever fooled with it was when a client called and wanted me to turn it OFF, because it was driving him crazy. But it is possible that somehow activating that link gave permission for Timeslips to talk to your Outlook, and now the emails are a third party beneficiary to those permissions. Which is all fine if it is working for you. And it may work for Lesa Cooper as well. But is not something I have ever done to get it work. Just saying...

Hope this helps everyone.

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]

The 32-bit version does not work either.  Someone named Roger who has advised he is the TOP muckity muck in your tech area is supposed to be working on this.  He is telling us it is an issue with GoDaddy being our e-mail/O365/domain provider.  Saying it has something to do with their overdone security.  We are a law firm - security is an issue for us.  We are attempting to get the two tech people together at one time to discuss between them without us as a less than knowledgeable middle man.  We would like to hold our breath and cross our fingers that this might work - but we would be goners if we did that!  I upvoted what you asked me to -- but we have tried so many different fixes at this point that even reading your e-mail is tiring.  Here is hoping Monday looks better and they powers that be can speak with each other directly.