Zimbra Outlook Connector

This is so AWESOME!
Just wait until you have to debug this EVERY DAY!
The Zimbra Outlook Connector (ZOC) is:

As defined on Zimbra's support site, the ZOC "provides real time two-way synchronization of mail, contacts, tasks, and calendar between Outlook and the Zimbra server." In other words, the connector makes it possible for Zimbra Communications server to, communicate natively with Outlook as if using Microsoft's proprietary MAPI protocol. Simply put, the ZOC is a plug-in for Outlook that makes Outlook think that it is sending to and receiving from a Microsoft Exchange mail server.

Mo's Professional Opinion about the ZOC:

For the most part, the ZOC works well and as intended. However, just like all workarounds and "bandages" the ZOC has it's issues and hiccups. Occasionally, you will receive the "local failure" error emails. The local failures are caused by a range of issues including, but not limited to, sync token mismatch and signature sync failures. In this post, I hope to provide you some suggestions to address your local failure messages, as related to signature sync failures.

Download the ZOC
Generally, you can download the ZOC from your mail server; unless your Zimbra representative asks you to use a different connector for which s/he will provide you a download link. To obtain the ZOC, simply browse to https://webmail.domain.com/downloads/index.html (remember to substitute the word "domain" with your domain name). In my case, the URL would be https://webmail.mchowdhury.com/downloads/index.html. Regardless, please consult you Tech Support and/or Systems Administration team for the specifics for your environment.

Ensure you save this connector to your hard drive, in a directory which you will remember. You will need this when you have to uninstall the connector and re-sync your mail profile.

Install the ZOC
The wonderful folks at Stanford University's ITS have compiled a very good tutorial on this, so I'll skip this.

Step 3: Fix the Signature Sync Error
No matter what I try, using an older version of the Zimbra connector, using the same version connector as the server, or using a newer version of the connector that the server, I've had end users complain of this issue. Hence, I recommend doing the following:

  • In Outlook, delete any signatures you've created:
    • Click File, then select Options
    • From the Options window, select Signatures
    • From the Signatures and Stationary window, highlight and delete/remove all existing signatures
    • If you're asked whether or not you want to delete the signature, select Yes
    • Close Outlook (ensure all Outlook.exe processes have been killed by checking the processes tab in Task Manager)
    • Open your browser and go to your webmail portal (i.e. https://webmail.mchowdhury.com) and log in
    • Switch to the Preferences tab
    • On the left hand side of the Preferences window, locate and select Composing
    • You will now see your options and settings for the message compositions. Change from text to HTML. Then select a desired font
    • Select Signatures from the list to the left of the window
    • Remove any existing signatures by clicking the clear button
    • Choose Add Signature and change the format to HTML and enter your signature, as desired. Upon completion, click Save and log out of the webmail portal
    • Open Outlook and allow for Outlook to sync with Zimbra