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

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.

And it's not even just a difference between Outlooks on platforms. Outlook for Mac 2011 does not suffer from the embedding problem, and neither do versions prior to v19 of OFM 2016.

The only way around it I've found to consistently avoid embedding in any Outlook is to programmatically set the signature HTML. This avoids the Word engine that's used in Outlook's signature editor so it doesn't have a chance to mess with any content.

Either that or you find a way down-stream in the email delivery to get the right signature in place.