Outlook v15.20 - signature now has image embedded not a link

Will need to look into Sigstr. Thanks for the direction. 

As far as the downgrade, set, upgrade workflow, what we've found is that all references to a current Outlook install must be removed prior to reverting/installing v19. From there, you can paste in your HTML signature, and it properly uses it Ex: pulls images from server rather than embedding and utilizes proper height/width attributes, renders any fonts correctly.

You can NOT however modify the signature after upgrading past v19 without succumbing to the embed issue, and rendering issues. Once you set it at v19 thats it. Your stuck. Definitely not a best-use scenario or really even practical, however it's what we're currently doing for our Mac install base. You can however upgrade other Office applications such as Word, PowerPoint, Excel.  Just not Outlook.

yes, it does have to be redone, and its deeply frustrating.

I've looked at Exclaimer, and other options, in the past but at the moment none are an option. We've got a lovely little HTML signature generator that works flawlessly for webmail / windows but is useless on mac.

Would also be interested in this programmatic solution?

Interesting that the "downgrade, set, upgrade" process works. I wonder if that whole flow has to be repeated if someone manually edits their signature *after* all that's been done.

I'm admittedly biased towards Sigstr as a solution (unsure if this forum has rules against self-promotion). We've got a client-side installer made specifically for Outlook for Mac 2016 that sets the default signature on the machine to match the design you create in our builder. This embedding problem is exactly what prompted the R&D.

Sigstr also has the cloud-based solution you mentioned, which obviously involves adjusting your mail routing, and we have those security conversations every day with IT & InfoSec staff.

I've spent the last several years working directly with the tech surrounding email signatures and am always happy to share what I can.

That is true. We are no longer on 2011, but your right that it didn't suffer from this issue as well.

We have found that installing versions prior to v19 and setting the signature first, and then performing delta upgrades from there also seem to work, though we haven't had to try it recently. 

Would you mind to explain how to set it programmatically? If needed we can take it off this thread

We had been looking into a 3rd party providers (ex: Exclaimer) that hook into Office365 and sends a signatures rather than using Outlook's built in version at all, but of course there are security concerns with that method our team is contemplating.