Pittsburgh Andy

Q: Suddenly iMail won't play nice with my Hotmail accounts.  Help?

Yesterday I received a Security Alert from Microsoft that someone may have accessed my two hotmail accounts.  I have had one for 20 years and another I've had for 10 years for professional/job-seeking use, and I can't just walk away from them unfortunately, even though Hotmail has never really played "nice" with iMail, occasionally falling into that loop where iMail keeps asking for passwords, etc.

 

For both accounts I went thru Microsoft's routines of changing my password as well as adding Google Authentication to both.  For one I even added an "app password," which was new to me -- for that one I use a special/different password for my iPhone just for that account.  For some reason that option exists for only 1 of the hotmail accounts.

 

At any rate, iMail needed new passwords obviously but wouldn't take any of the new ones.  I deleted both hotmail accounts from iMail and re-introduced them.  iMail seems to receive mail from them no but won't send any.  Outgoing messages just sit in the Outbox. 

 

I have Lion version 10.7.5 and version 5.3 (1283) of mail, a few generations old since I'm limited with my 2006 mac.

 

Anyone recognize this and have any advice?  Thanks a lot.

Mac Pro, Mac OS X (10.7.5)

Posted on May 17, 2014 4:20 AM

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Q: Suddenly iMail won't play nice with my Hotmail accounts.  Help?

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  • by Pittsburgh Andy,

    Pittsburgh Andy Pittsburgh Andy May 17, 2014 6:06 AM in response to Csound1
    Level 1 (0 points)
    May 17, 2014 6:06 AM in response to Csound1

    Csound1 - I forgot the other screen shot.  Here are both in case you're still around:

    Thanks.

     

    Screen Shot 2014-05-17 at 8.27.56 AM.png

     

    Screen Shot 2014-05-17 at 9.04.21 AM.png

  • by Pittsburgh Andy,

    Pittsburgh Andy Pittsburgh Andy May 17, 2014 6:07 AM in response to Csound1
    Level 1 (0 points)
    May 17, 2014 6:07 AM in response to Csound1

    Csound1 - I hear you, believe me, what a pain.  But I'm posting here since my main issue is that Mail @my mac pro won't send mail.  I have everything else working happy - iphone, ipad, etc.  In fact I can receive mail at my mac pro Mail app, just can't send.  painful!!

  • by Csound1,

    Csound1 Csound1 May 17, 2014 6:08 AM in response to Pittsburgh Andy
    Level 9 (50,511 points)
    Desktops
    May 17, 2014 6:08 AM in response to Pittsburgh Andy

    This is a question for the vendors whose services those are, not Apple.

  • by peter_watt,

    peter_watt peter_watt May 17, 2014 6:09 AM in response to Csound1
    Level 3 (910 points)
    May 17, 2014 6:09 AM in response to Csound1

    Agreed.  I would never use two step authentication whilst trying to use email clients anyway.

  • by Pittsburgh Andy,

    Pittsburgh Andy Pittsburgh Andy May 17, 2014 6:18 AM in response to Csound1
    Level 1 (0 points)
    May 17, 2014 6:18 AM in response to Csound1

    Frustrating.  Having gone in and out of my accounts the past 2 days, it seems that the authenticator app is just for when trying to get to the Security Settings for either hotmail account, or when trying to change the password from the homepage of www.hotmail.com w/o having logged in first.  So I'm pretty sure the authenticator has nothing to do with my apple mail problem.  I just mentioned the fact that I added all kinds of new security options to my hotmail accounts yesterday thinking that maybe one is causing my can't-send-mail problem.  I'm pretty sure they don't matter, since I can receive mail with my mac pro mail program....just can't send....even after re-setting up the accounts.  Seems like it'd be an Apple problem but who knows.  So very very frustrating, right on top of my (red herring alert) frustration with ios7's horrible interface and design and frustration with the entire online community follwing like lemmings into this boring flat design cliche that makes things more vague and harder to navigate rather than easier! 

     

    Anyone who can help me fix my can't-send issue will be sent a $10 starbucks gift card - first one to solve the issue gets it, ha ha.  Please help me if you can.    Thanks!

  • by Pittsburgh Andy,

    Pittsburgh Andy Pittsburgh Andy May 17, 2014 6:19 AM in response to peter_watt
    Level 1 (0 points)
    May 17, 2014 6:19 AM in response to peter_watt

    Peter - I think the two-step is great in this sense - it's much easier for me to wade into my account using a separate authenticator app if there's an issue with my password.  Now, having to go thru 2 steps when accessing email from a new computer - yes, that may be causing the problems, who knows.  So strange that I can receive but not send.  Argh.

  • by Csound1,

    Csound1 Csound1 May 17, 2014 6:52 AM in response to Pittsburgh Andy
    Level 9 (50,511 points)
    Desktops
    May 17, 2014 6:52 AM in response to Pittsburgh Andy

    Set it up without the authenticator app, if you are right it still won't work. But I suspect it will.

     

    I found this (largely confusing) guide on how to use it, see if it helps.

  • by peter_watt,

    peter_watt peter_watt May 17, 2014 7:36 AM in response to Pittsburgh Andy
    Level 3 (910 points)
    May 17, 2014 7:36 AM in response to Pittsburgh Andy

    i would rather not try to use it, but if you do, from what I have been reading about it, you need to generate a single use application specific password for Mail in hotmail.com (outlook.com) then set up the account as new in Mac using that throwaway password.

  • by peter_watt,

    peter_watt peter_watt May 17, 2014 8:41 AM in response to peter_watt
    Level 3 (910 points)
    May 17, 2014 8:41 AM in response to peter_watt

    I have tried it on a new account. I can't find any way of getting Mail (or Airmail) to acceot the wierd passwords.  Can receive but cannot send, same as you.

     

    The options for devices are...

     

    Screen Shot 2014-05-17 at 16.35.55.jpg

     

    Then Mail crashed.

     

    Turn off two step verification is now my advice same as Csound1's was.

  • by Pittsburgh Andy,

    Pittsburgh Andy Pittsburgh Andy May 17, 2014 9:12 AM in response to peter_watt
    Level 1 (0 points)
    May 17, 2014 9:12 AM in response to peter_watt

    Peter - bad news is that I have had two step verification shut off for the past day. 

     

    I removed every account from my Mail app on the mac and will try re-loading them.

     

    I can't find another good mail program to use that will let me access icloud, hotmail, and gmail in one program....

  • by peter_watt,

    peter_watt peter_watt May 17, 2014 9:58 AM in response to Pittsburgh Andy
    Level 3 (910 points)
    May 17, 2014 9:58 AM in response to Pittsburgh Andy

    I use Airmail from the App Store. Couple of bucks.

  • by Pittsburgh Andy,

    Pittsburgh Andy Pittsburgh Andy May 17, 2014 12:56 PM in response to peter_watt
    Level 1 (0 points)
    May 17, 2014 12:56 PM in response to peter_watt

    Peter I'm loving airmail.  A million times better than the standard Mail app.  If I have no password or other problems with airmail, you win the starbucks, assuming you're a starbucks fan?

    Thanks a ton - so far so good. 

     

    Asking for a replacement for Apple's standard mail app was the real question I should have asked.

  • by peter_watt,

    peter_watt peter_watt May 17, 2014 1:15 PM in response to Pittsburgh Andy
    Level 3 (910 points)
    May 17, 2014 1:15 PM in response to Pittsburgh Andy

    In the UK that brand will only be popular when they change their corporation tax practices, but I will have a Costa coffee instead. Airmail has improved a lot in the last six months and IMAP webside folders makes it easy to change.  Airmail not so easy with local folders.

  • by Pittsburgh Andy,

    Pittsburgh Andy Pittsburgh Andy May 17, 2014 1:18 PM in response to peter_watt
    Level 1 (0 points)
    May 17, 2014 1:18 PM in response to peter_watt

    Do you mean local folders as in - on the computer itself?  The most important thing to me will be to be able to access the folders in icloud both in airmail and away from home on the ipad & iphone.  What limitations do you speak of specifically?

     

    I'll look for Costa coffee online then...

  • by peter_watt,

    peter_watt peter_watt May 17, 2014 1:19 PM in response to peter_watt
    Level 3 (910 points)
    May 17, 2014 1:19 PM in response to peter_watt

    By the way Airmail will add three folders (to do, reminders etc) to all your accounts webside. Even in iCloud account.

    You can turn that off in the settings of each account and delete them from there if it annoys you, but they do no harm.

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