The Definitive Guide to Troubleshooting Outlook Calendaring Issues.

If you work in an environment with multiple versions of Outlook crossing multiple time zones (especially those in the US with Daylight Savings Time), I absolutely promise you that you will see a lot of issues, particularly with Outlook 2010 now in the mix. Knowing everything below should give you the information you need to bring an issue to resolution without escalating it… which is exactly why I wrote it for our help desk 😉

First, I highly recommend that you read through the following guides:

Outlook meeting requests: Essential do’s and don’ts

How to troubleshoot missing and duplicate appointments in Outlook

These guides contain a ton of useful information you should know in order to adequately troubleshoot issues related to meeting requests either disappearing or not behaving as expected.

In regards to an appointment displaying at the wrong time (generally off by 1-2 hours) for an attendee, thoroughly review this document.

How to address time zone changes by using the Time Zone Data Update Tool for Microsoft Office Outlook

If absolutely nothing else, please remember these points:

  1. If the user has Outlook installed on multiple machines, and the determination has been made to rebuild the profile, then the Outlook profile must be rebuilt on all machines, including deleting the existing OST file.
  2. It makes a BIG difference if Outlook 2010 is anywhere in the mix.  Microsoft made major revisions to how Outlook calculates meeting times with 2010.  Delegates (i.e. EA’s) and their executives should all be upgraded simultaneously to the same version of Outlook.
  3. Meeting times are calculated.  That means that an appointment doesn’t start at 1 PM CST, it starts at “7 PM -6 GMT,” and the endpoint decides what that means by performing the calculation based on what it knows about the meeting time and the organizers Time Zone.  The Exchange server plays no role in that unless you are viewing it through Outlook Web Access.  This is why a meeting start time may be different on an iPhone than it is in Outlook, because each one independently decides when that meeting really starts.
  4. If a meeting time differs from where it is supposed to be, there is a mismatch of time zone/DST settings with either the meeting organizer, their delegate, the attendee, or the person that forwarded the meeting request.  Any Outlook client that touched that meeting request must be thoroughly vetted.  Again, if 2010 is in the mix (particularly the end point), that’s a big issue and the user should be taught how to use the Time Zone Data Update Tool.
  5. Time zone settings are set in both Windows and in Outlook.  The DST settings are set in Windows.  All of them are equally important and you should verify they match.
  6. An end user should ALWAYS have the “Automatically Adjust for DST” flag set in Windows unless they live in a time zone that does not recognize DST.  Simply setting the clock +/- one hour is insufficient.
  7. When looking at the Outlook calendar, always switch to “View by Category” or use Outlook Web Access in order to know 100% that a meeting isn’t really there.
  8. If a meeting does not exist in Outlook, Outlook Web Access, or on a mobile device, then it simply does not exist.  It’s gone for good and will need to be recreated.  None of us can bring it back so light a candle and say a prayer.
  9. Remember, OST files get corrupted, NK2 files get corrupted, and PST files are just flat out evil.  Know what each of those does and how to correct them.  Read up on ScanPST.exe, you can use it for OST files too.

…and last but not least, at my very first job in IT my manager drilled this in to me:  “We do not work on unpatched software.” That means the very first thing you should do with Outlook is verify it is on the latest service pack (and it wouldn’t hurt to check for hotfixes).  It won’t always fix the issue, but at least you are working with the latest code.

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