I want to see if this could be related to using IManage with Citrix. There is a registry change I would like to try to see if this my be causing the strange behavior. If you are able, let's try a test with the setting disabled (you can then see if it makes any difference and then change it back if needed to the original setting). I found this workaround on the Imanange website:

The ValidateCheckoutLocation registry setting was added to fix NT-71246: If users are connected to a Citrix farm, they cannot check in a document from a Citrix machine.

This issue occurs because during check in, the document's checkout location is validated against the current machine name of the logged on user. To bypass this check, add the following registry setting and set it to 0 (disabled):

Path:

For all users:

HKEY_LOCAL_MACHINESOFTWAREiManageWork10.0Client
OR

For each logged on user:

HKEY_CURRENT_USERSOFTWAREiManageWork10.0Client
If the registry setting is not found at either location, the default value (1) is enabled.

Type: DWORD

Name: ValidateCheckoutLocation

Values:

0: Disabled"