I'm no expert on the subject, but here are some random thoughts to check out (or at least, ponder):
- Does this happen anywhere he travels, or just a few problem hotels? E.g., if he's in Russia or Ukraine, those places are full of spammers and hackers. Tell Jared he should use a State Department-issued system .
- How finely does the IP address resolve -- i.e., is it just his laptop, just the hotel, or a wide swath of the country?
- I don't doubt that he is entering his password correctly, but if a bunch of hackers are also on the same IP (see above), that could be tripping something protective.
- Is this setup compatible with a hotel or local provider who is constantly changing the IP address (dynamic assignment), or is the IP address fixed for long periods? Maybe something in IMAP or Outlook just doesn't like that.
- If a different user (someone else) signs on with the same IP address, could that get the system confused (i.e., it's trying to cache IDs and IPs, and constantly getting mismatches)?
He is on the edge of being frustrated enough...
I assume that "he" refers to the Traveling Wilbury with 2.6GB, and not the non-traveling 6GB guy?
Hope the above may give a clue to someone about how to deal with the problem.