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When I connect to a library with checkin/out and versioning enabled I get the following message when checking out and editing a file

"This document could not be checked out to your local draft folder. The document may have already been checked out or the local drafts folder could not be written to."

This only happened when I am VPN onto the network. The SharePoint site is seen as being in the Local Intranet Zone.

On the same machine when I am on the LAN it all works fine.

Am I supposed to be configure something special when using VPN?

I am running MOSS 2007 sp2.

Update: I tried creating a new web application. And it seems to not have the same issues with VPN. I am now trying to see what is different between the two. It may be related to a solution or feature I have deployed.

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Please verify your Alternate Access Mappings. If I remember correctly I had this problem and fixed it by setting correct AAM settings.

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Thanks I checked AAM and it seems fine. – Anonymous May 4 '10 at 0:59

I've experienced a similar issue over VPN. Our issue was because there was no DNS resolution setup for the portal through VPN, and the only way to access it was via IP address unless you were on the LAN.

As Wictor stated above, once we either fixed DNS or setup an AAM in SharePoint for the IP address, it resolved the check-out issue.

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