Outllook renaming attachments after they have been sent

In the office we are experiencing an issue where users will attach two documents to an email and after they have been sent the second attachment will take on the first attachments name including the document type. There is also situations where an older version of an attachment will be sent in an email rather than the current one. We have tried clearing the cache, Office repairs, disabling add-ins and reinstalling Outlook but this has not resolved the problem.

Any assistance would be greatly appreciated.

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Jacko1969Connect With a Mentor Author Commented:
We had found that the root of the problem relates to Outlook drafts. If we allow an attachment to save to draft and then send we experience replicated attachments.
Jacko1969--To what document type is the change made?  Is it .dat, by chance?
Jacko1969Author Commented:
Thank you very much for your response, the document type changes to the type of the document which is attached first which it has taken the full name of, however if we change the doc type to what it should be we are able to open the attachment. We haven't had any occurrences where file types have changed to.dat as yet.

Thank You
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Out of curiosity, what happens if somebody does the following?

1. Open Windows Explorer and locate two files with different file names and different file extensions (eg. File1.xls and File2.doc) in the same folder.
2. Select both (Click then Ctrl+Click for next).
3. Right-Click > Send To > Mail Recipient.
4. A new message opens with both the files attached.
5. Insert recipient, Subject Line and message body, and send email.

Does the same issue affect the attached files on receipt?
Jacko1969Author Commented:
Hello BillDl

Thank you for your advice when sending mail as suggested the same issue doesn't affect the attached files however the issue is rather intermittent and hard to predict. It appears to randomly affect different users even though they are all working from Outlook 2007 Service Pack 3 and updated.

Jacko1969Author Commented:
This workaround is suitable for us.
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