We are running 5.0.19 NE and we have an issue where Documents / Wiki pages that have images prompt users for their username and password once for each image in the document. This is REALLY annoying. I read somewhere (can't remember where) that it has to do with having the Public Service Hostname set for the affected domains. We do this as a practice since we've seen issues where some client applications don't work correctly without it since we're running self-signed SSL certificates. Anyway, we did try removing the PSH and this cleared up the issue for a while but then we started seeing it again, so we've added the PSH back.

We have found that if the user enters their complete email address as their username in Zimbra Web, they don't get prompted for auth for each image in a document. This isn't ideal either since the users expect to be able to enter their short username as long as they are pointing their browser at host.primary-domain.com as the Zimbra documentation spells out.

Does anyone else have any experience with this and know of a way to fix this issue?