What gives you best chance of an upgrade: mobile check-in as early as possible or wait and try to schmooze front desk in person? (Marriott, ambassador status)

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Front desk by far.

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Honestly, using the text ahead feature has worked great for me. Usually as good as desk (if I couldn’t get it via mobile then I also couldn’t get it when physically arriving barring cancellations)

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I'm also ambassador - imho mobile checkin is the least likely option to get an upgrade. the best is a quiet $20 to the front desk person. as my so says, "if you want to get VIP, watch what Inventing Anna"

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