Outlook 2010 reminders gone when roaming from 2007 to 2010

**The setup**
Email: Exchange
User profiles: Roaming
Outlooks Cached Mode: Disabled

Users main PC
OS: Windows 7 32-bit
Microsoft Office Version: 2010

Users secondary PC’s
OS: Windows XP 32-bit
Microsoft Office Versions: 2003 & 2007

This user was initially on a Windows XP, 32-bit OS, with Microsoft Office 2007.  I upgraded this user to a new pc with Windows 7, 32-bit OS, and Microsoft Office 2010.  The transition to the new laptop was simple and non-problematic.  Everything concerning this users Outlook 2010 transitioned and functioned flawlessly.

A few months later this user needed to work from another location within our building.  The computer this user was working from at the new location had Windows XP, a 32-bit OS, and Microsoft Office 2007.  Again, the transition was flawless because of the roaming profile and everything functioned flawlessly upon logging in.  The next day this user went back to working from the computer with Windows 7, 32-bit OS, and Microsoft Office 2010, but this time there was a problem.  The reminders for all of this user’s tasks and calendar items were 100% gone.  The appointments and tasks themselves were still present, but the reminder box never automatically popped up.  When I manually opened the reminders box I discovered that it was empty.  Nothing was listed in it, but I know, and even verified that this user has over 50 reminders that are still present - they should have popped/shown up.

**Diagnostics I have already performed**
1.  Logged user in at a pc that this user had never logged in to before that was also a Windows 7, 32-bit OS, with Outlook 2010 – issue was still present.
2.  Logged user in at a pc that this user had never logged in to before that was Windows XP, 32-bit OS, with Outlook 2007 & 2003 – reminders work/display flawlessly.
3.  Logged user in to Outlook Web Access interface – reminders work/display flawlessly.
4.  Logged user into Windows 7 pc again and tried the “outlook /cleanreminders” and “outlook /resetfolders” commands – issue was still present.
5.  Logged user into Windows 7 pc again and removed Outlook profile via control pannel and re-created it again with different name, then redid everything with original name (loaded new OST both times) – issue was still present.
6.  Performed everything in step 5 and then repeated step 4 – issue was still present.

**How I fixed the issue temporarily (I don’t like/want because it’s just a ’Band-Aid’ fix)**
1.  Enabling cached mode resolved the issue.  Now that I know this works – I wonder what will happen when this user goes back to the pc with XP and Outlook 2003/2007 again….  I am afraid to even ask because if whatever messed up this users Outlook in the 2003/2007 version follows the roaming profile to the Windows 7 pc then I could potentially be screwed all over again and this time I wouldn’t have the luxury of enabling cached mode because it is already enabled.  I think I would have to try deleting/restoring this users roaming profile to get things working at that point.  

For those of you who may be thinking “Why not try disabling cached mode and seeing if that works again?”, My Response - I don’t care, because even if it did work I would not want my user(s) having to go in and check/un-check that each time they login from one version of a computer/Microsoft Office to the next – this is not a long term solution.

**What I didn’t try, but think would have also worked**
1.  I believe that deleting this users roaming profile and having it re-created from scratch would have also resolved the issue, but of course this would have taken a lot longer due to having to manually restore all the users’ settings, moving data, etc…  There would also still be an issue when the user logs in at a computer with Outlook 2003/2007, which would just result in redoing the user profile all over again.  This would not be a long term solution either.

**What I am looking for**
1.  I want a long term answer/solution that would allow users go from multiple OS and Office platforms without usage restrictions – by software or by telling a roaming user that they can no longer roam from one computer to another anymore.  Who knows, maybe there is no other way around this other than to tell a user that they can no longer roam between 2010 and 2007/2003 Outlook, or maybe if they did roam between these versions that when on the 2007/2003 computers that they would have to remember to only use Outlook Web Access…   I would hate to even have to propose such a plan because users will just forget anyway and I would still be screwed.  

Any ideas?  Anyone???
Who is Participating?
Rodney BarnhardtConnect With a Mentor Server AdministratorCommented:
There are some known issues. You can try creating Outlook Profiles, as described in the link below, this also discusses some of the known issues in the "Important" box

NCC_ITAuthor Commented:
Wow, that is one long article.  I appriciate the link, but it will take me a while to go through and try all of that.  I'll eventually respond here and let you know if that works or not and and award points accordingly.
Do the workstations with Office 2010 installed, also have Office 2010 Service Pack 1 (SP1) installed?

If this is the case you may want to consider installing the following hotfix: http://support.microsoft.com/kb/2584053

This hotfix has resolved "missing reminders" issues that we have had on a number of our workstations, although, unlike your case, we are not using roaming profiles.

If you can, log this affected user onto another (previously untested) workstation with Win7 32-bit OS and Office 2010 SP1 with abovementioned hotfix applied.
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