I am using Outlook 2003 and have all my contact separated into categories. I tried imported the .csv file and only uploaded about 10% of the contacts. Next, I whet to Zimbra webmail and setup tags to match my categories and tried importing again. Only the contacts that were imported the first time added tags, but all the other tags I added were remove form the tag list in webmail.
I have been uploading one group at a time, by setting up a tag in webmail, then sending myself v-cards from my original outlook profile to my Zimbra profile in outlook then hit send/receive and it seems to work, but then I added a category in outlook without setting up a tag in webmail. After the next send/receive outlook and webmail removed almost all of the categories and tags.