Google Apps Calendar Invites Getting Stuck in Outlook 2010 Outbox

I have a client using Google Apps for Business for her email. She uses Outlook 2010 as her email client. She recently started having a problem. When she creates a calendar entry and tries to invite attendees, the invitation email ends up getting stuck in her Outbox and so the person being invited never receives the calendar notification.

The odd thing is that when I have the user delete the entry from her calendar, the cancellation email sends out w/ no problem.

I tried using scantpst utility to repair her PST file, but the issue persists.

Found this link on the Google Apps forums, but it's a few years old and recommended solution is to create a brand-new profile, which won't work for this user b/c she has many email categories, calendar categories & flags and does not want to lose them when moving to a new Outlook profile.
http://productforums.google.com/forum/#!topic/apps/2YzgOan-57E

Anybody else come across this?
anuneznycAsked:
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Allen FalconCEO & Pragmatic EvangelistCommented:
I haven't seen this before.   One option is to remove the cache and re-sync using Google Apps Sync for MS Outlook.  Categories may not be preserved, but flags will.
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anuneznycAuthor Commented:
Thanks. How do you remove the cache?
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Blue Street TechLast KnightCommented:
Hi anuneznyc,

Here is how to clean out the cache: http://www.ehow.com/how_7165299_clean-outlook-cache.html
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anuneznycAuthor Commented:
I could not find any of the files referenced in that link. No "dat" file, ".fav" file, ".nk2" file or ".oab" files.

I don't know if these are only used in pre-2010 versions of Outlook, or if Google Apps Sync just doesn't use them.
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Blue Street TechLast KnightCommented:
I trying to go about this as you have requested, by not creating a new profile, but honestly that is the best approach here.

Categories, which are select for items, will transfer over. For example if she has used a category for any item that item will retain the category. If she has never used a category it will not transfer over. The main list of categories will initially be blank but she can simply add them back when she comes across an item that has a category. Flags will transfer OK. Here's what I'd recommend. This will give you a completely clean starting point.

1. Make a PST backup of her file. Here's how: http://support.microsoft.com/kb/287070 under "How to make a backup copy of a .pst file" section. Store the backup PST on your Desktop.
2. Delete all files within directory: <drive>:\Users\<user>\AppData\Local\Microsoft\Outlook.
3. Delete the old profile. Go to Start > Control Panel > Mail > Show Profiles... then select the profile and click Remove.
4. Reboot the PC.
5. Add the new Profile. Follow the steps in #4 above but instead click Add and follow the prompts.

Keep in mind when running ScanPST you have to follow specific procedures in order to make it work. Running it once will not work ever unless all the corruption is fixed in that initial run, which is typically not probable. See this for more details about how to execute ScanPST/OST:
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anuneznycAuthor Commented:
Thank you very much, diverseit.

Did you mean to post a link (re: ScanPST) there at the end of your last post?
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Blue Street TechLast KnightCommented:
My EE article has not been published apparently, which was the missing link. Sorry about that.

Anyway, the short of it is you must re-run the ScanPST.exe on your PST files until you get a result of no errors. Simply running it once isn't enough unless it finds no errors on the first run, which is not likely. So run it & it will discover say 5 errors, then it will fix then. Next re-run again and typically it will find more that need to be fixed. Re-run until it doesn't find anymore. After that I like to create a new PST file and import everything into it so you have a clean slate gong forward.

Make sense?
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anuneznycAuthor Commented:
Yes, makes sense. That's annoying that it has to be run several times, but oh well. Thanks.
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Blue Street TechLast KnightCommented:
My pleasure! Did it work?
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anuneznycAuthor Commented:
This is a remote user in another city. I have not had a chance to remote back into her laptop again in order to try re-running ScanPST.
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Blue Street TechLast KnightCommented:
Gotcha!
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anuneznycAuthor Commented:
I was able to remote into this user's laptop and I ran the ScanPST tool on all 3 of her PST files until they reported no errors found. Unfortunately, she is still having the original problem. :-(
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anuneznycAuthor Commented:
I had opened a support ticket with Google Apps and these were their suggestions.

1. PST permissions problem. This issue typically occurs when there is a configured limit to the user's .pst file size (using a registry override). Further information regarding these registry settings and their removal is available in this article http://support.microsoft.com/kb/832925.

2. Possible Anti-virus software related issue; Try to use Outlook on safe mode or deactivate the Anti-virus for testing purposes; Refer to this link to set outlook in safe mode http://www.outlook-tips.net/beginner-user/start-outlook-in-safe-mode/.

3.There may be transient connectivity issues with Google Apps servers. Please check that you are able to connect to http://mail.google.com/a/foo.com. If you are able to connect without issue, then ensure that the following URLs are available on your network through port 443:

Signing: https://www.google.com/accounts/ClientLogin
Calendar: https://www.google.com/calendar/feeds
Contacts: https://www.google.com/m8/feeds/contacts/
Email: https://mail.google.com/a/[domain]/r/
Email Migration: https://apps-apis.google.com/a/feeds/migration/2.0/[domain]
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anuneznycAuthor Commented:
I think this user might just have to recreate her entire profile. She is going to be upset about having to recreate her rules and custom category definitions, but at this point I don't know what else to do?

This is the link Google recommended I follow for removing her profile:
https://support.google.com/a/users/answer/160659?hl=en
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Blue Street TechLast KnightCommented:
The link they supplied is not a complete way of removing a profile.

Follow what I provided you here (http:#a39488617). That will ensure this issue does not happen again at least from your side of things...google's we can't say!

I'd create a connection with the new profile first and test to make sure everything is operational before importing the backup.
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anuneznycAuthor Commented:
Sorry if it's a dumb question, but why do we have to import the backup of the PST after creating the new profile. Google Apps Sync should pull in all her emails and calendar entries once it creates the new profile, no?

Won't importing the backed-up profile create duplicates?
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Blue Street TechLast KnightCommented:
I'd rather you be on the safe side of having a backup because I didn't know how you were connecting her, i.e. EAS (Exchange ActiveSync), IMAP or POP (all are supported by Gapps).

Obviously if by IMAP or POP (both not the recommended way to connect) they would not sync anything except mail (only on IMAP).

If by EAS, not sure they way Google has written it that it would include her categories or flags. EAS is not written by Microsoft for third-party companies (like google, apple, etc), but rather only licensed. Therefore, again as a pre-caution its always good to have a backup. If everything works out...great don't use the backup but if something is missing you always have it. This idea is part of a zero data loss policy.

Make sense?
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anuneznycAuthor Commented:
OK. Makes sense.

So I won't import the backup unless there is a problem.

Yes, I believe that Google Apps Sync must use EAS in order to offer "full" (I use that term very loosely in Google's case) synchronization between devices. From my experiences clearly they have not implemented EAS anywhere near as reliably as most traditional hosted Exchange companies like Intermedia.net!
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Blue Street TechLast KnightCommented:
I agree! Let me know how it goes.
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anuneznycAuthor Commented:
Today I spoke to the support rep at Google Apps that has been managing the trouble ticket I submitted. She told me that just today Google release the newest version (v 3.4) of Google Apps Sync.

Think I'm going to download that version and let it create a new profile.
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anuneznycAuthor Commented:
According to this link (https://support.google.com/a/users/answer/160659?hl=en), creating a new Outlook profile will result in the loss of the email signature, rules, and custom category definitions.

The signature will be easy to re-create, but do you know of any way to migrate the rules & custom categories over to the new profile?
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Blue Street TechLast KnightCommented:
Yes, for Outlook 2010 follow this guide to export the rules and then import them in the new profile: http://office.microsoft.com/en-us/outlook-help/import-or-export-a-set-of-rules-HP010355072.aspx?CTT=1

Unfortunately since Outlook 2007, Categories has moved from the registry to the PST. You can have a look here: http://www.slipstick.com/outlook/outlook-categories-and-color-categories/ 

Here are a few workarounds: http://www.outlook-tips.net/how-to/back-up-master-categories/ and similarly: http://www.msoutlook.info/question/611

The only other way to get Categories in is by importing the backup and during import select replace existing items. That will bring in the categories and then you can easily assign them to the Master Category List.

May I suggest Office 365 for this user. It's far superior to Google Apps and in this same scenario (if you even had an issue, which is not likely) you would simply trash the profile and create another...all of these settings (flags, categories, rules) would be stored on the server. I have some 30-day trial links on my about us page: http:M_5170946.html. You can get an online Exchange account for $4/user!

Let me know if you need anything else!
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anuneznycAuthor Commented:
OK. Thank you. I think that latest version of Google Apps Sync did the trick.
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Blue Street TechLast KnightCommented:
Great! Is there anything more I can help you with?
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anuneznycAuthor Commented:
Thank you, Diverseit. I'll assign points & close out now. Thanks again!
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anuneznycAuthor Commented:
Excellent suggestions & follow-up. Many thanks.
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Blue Street TechLast KnightCommented:
I'm glad I could help and thanks for the points!
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