Personas used to work in the following way on both the AJAX Web client and the Outlook connector (in my case, Outlook 2003 SP3 w/ all current MS updates): I had a number of external POP accounts defined as well as corresponding personas (identical "From" specified in both external account and persona definitions, the latter so that I have something in the drop-down "From" list on the web client), and in every case, replying in Zimbra to an email fetched from one of those external accounts would automatically set the "From" address of the reply to the one specified in the relevant persona and/or external account definition; no specific "Reply-To" header needed to be set. Very convenient mail management feature, especially if you have multiple email accounts and don't want to leak your other email addresses to a recipient, but after my Zimbra provider upgraded past 5.0.6, it no longer worked. I've done all the usual things my email: downgraded the connector, upgraded the connector, each time synchronizing a completely new Zimbra connector local store.
These automatic features of personas and external accounts no longer work; my Zimbra provider can't understand why.
Can anybody suggest local and server-side avenues to resolving these problems? Using Zimbra to manage multiple email accounts is a major feature for me.