Trouble saving documents from Outlook to SharePoint 2010 library - missing tags

Hello
One of our users is seeing a strange issue with saving documents from Outlook. It appears that the document already had tags from the library, but the user said the document was never uploaded to the library.
All of the server tags show Currently Unavailable, and the user cannot upload this document to the library.
See screen shot:
Please advise,

Hi thematrixhasyou,
According to your description, my understanding is that you want to update documents from Outlook to SharePoint 2010.
I did a test as the followings:
1. Create a library, and allow Content Type as Library settings->Advanced Setting, under ‘Allow management of content type?’, select Yes.
2. Click on Library Settings->Document under Content Types, click on Document Information Panel settings, and select ‘Always show Document…’.
3. Create some custom cloumns
4. Upload some documents to the library
5. Then click on Library->Connect to Outlook, the library will be synced to Outlook
6. In Outlook, find the library
7. Double click a document, the document was opened, and the document information(Title and custom columns) were displayed correctly.
8. Change the document, and save it
9. Then close the document, it pop up a dailog box, like the below screenshot.
10. Click on Update, then the document will be updated in SharePoint
Which type did you use for the custom columns (Year, Category, Document Type)?
Please have a try as the above steps.
I hope this helps.
Thanks,
Wendy
Forum Support
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Wendy Li
TechNet Community Support

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Hi thematrixhasyou,
According to your description, my understanding is that you want to update documents from Outlook to SharePoint 2010.
I did a test as the followings:
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Which type did you use for the custom columns (Year, Category, Document Type)?
Please have a try as the above steps.
I hope this helps.
Thanks,
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