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I have a gmail address, say, x@gmail.com and a me.com address, say y@me.com. If I use the web based iCloud email client for my me.com account, and I send an email to the following 3 versions of the gmail address:

  1. x@gmail.com
  2. <x@gmail.com>
  3. "x" <x@gmail.com>

Only #3 gets delivered! Neither the me.com or gmail.com account have any forwarding or filters of any kind. x is a string of alpha-only characters. How can this be?

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  • Hm, I can't reproduce this problem.
    – jan.h
    Mar 4 '12 at 17:04
  • Nor can I when I use a different gmail acct. It seems to be just this one. I'll also add that when I do the same experiment sending from a yahoo.com email account, all 3 are delivered.
    – Robot
    Mar 4 '12 at 17:29
  • How about the same experiment, but sending to the Yahoo account?
    – Tuesday
    Mar 5 '12 at 4:07
  • When you say "alpha-only" characters, you mean [A-Za-z]? No punctuation or anything? Diacritics? Unicode? Just ASCII upper and lower case letters before the @ sign? Curiouser and curiouser.
    – Daniel ♦
    Apr 10 '12 at 4:36
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You could very easily figure out what's happening by copying a neutral email address (or your iCloud address) on each mail.

Either all three messages get to the CC address or not. At that point, assuming iCloud is delivering, you could inspect the mail headers and determine if iCloud is sending the mail appropriately.

At that point, you would open a support ticket with either iCloud (if all three do not get sent) or with Google (if all three do not arrive in your account) and provide them the Message-ID that iCloud generated for each problematic email as well as the date/time It passed through the iCloud relays

Message-ID: <515c2f8bef24f_7a303fde14661752@jobs-01.mail>

Received: from mail-relay-03.basecamp.com (mail-relay-03.basecamp.com [204.62.114.94])
    by spool.mail.whatever.net (Postfix) with ESMTP id 412011162EA
    for <bmike@whatever.com>; Wed,  3 Apr 2013 15:33:01 +0200 (CEST)
Received: from jobs-01.sc-chi-int.37signals.com (bigip-floating-public.sc-chi-int.37signals.com [10.10.0.20])
    by virt-gw.sc-chi.37signals.com (Postfix) with ESMTP id 071654440F
    for <bmike@whatever.com>; Wed,  3 Apr 2013 13:33:00 +0000 (UTC)
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