We’re seeing a rash of “Error: 5102. Server. Maximum request length exceeded” errors when using the Outlook Hotmail Connector. This specific error is caused by trying to send a file larger than 4MB using the connector. The problem behind the error should be fixed in a couple of weeks or so, but until then, if you get the error, delete the message from your Outbox. This should get rid of the error and allow the Outlook Connector to work again.
If you need to send larger attachments, use the web interface.
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