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  1. #1

    PGB1's Avatar
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    2007 Mac Book Pro 2.2 Ghz 4 GB RAM SSD OSX 10.11 & 2006 MBP Stuck At 10.6.8
    iOS Mail Sends, But Message Is Never Delivered
    I am sorry to pester you all with this, but I have searched here and on the innerweb a whole lot for several days & I still can't figure out what I am doing wrong.
    My wife recently got an iPad Pro and we are both novices with iOS. The iPad has one e-mail address account on it. It is a POP account (how we have all of our mail accounts set up).

    In Mail, if we send a message, we hear the Sent sound and see the message in the iPad's "Sent" folder. But, the recipient never receives the message.

    I can check on the recipient's device and at the Mail server at the recipient's ISP. The message isn't there. It isn't in the junk mail folders, either. This happens no matter if we try sending a brand new message, a reply or by clicking the Share button from Safari.

    The iPad receives mail fine.

    While We Are Sure We Are On Line, We Have Tried-
    A) Making sure the iPad has the latest software updates.
    B) Sending messages to people with various ISP addresses, such as sbcglobal, wowway, gmail, ymail, corporate accounts & more.
    C) Carbon Copying new messages to many people to see if one of them gets sent. None show up.
    D) Verifying the settings for outgoing mail are exactly as the ISP wants them to be. They match our OS X Mac Mail settings to the letter.
    ......During original account setup the iPad picked the wrong outgoing port, so we changed it to what the ISP wants & matches our OS X devices.
    ......Going back to iOS's suggested port didn't solve the problem.
    E) Waiting several days to see if the messages show up.
    F) Checking on the recipient's ISP's web site to see if the message showed up.
    G) Sending from the same e-mail account to the same addresses, but on the computer instead of the iPad. Those OS X-sent messages do get delivered.

    I'm out of ideas.
    Is there something I am supposed to do with iCloud so Mail will send?
    Is iCloud somehow tied to, and required for, Mail sending? My search results say no, but I get really confused about such things.
    iCloud is set up and backing up the iPad, so we must have done something to initiate this iCloud account. (As hard as I try, I stay confused about iCloud.)

    Is there something I've missed in my Mail Not Sending troubleshooting?

    Thank You All for helping out & I apologize if the solution is something obvious that I should have figured out.
    Paul

  2. #2

    mrplow's Avatar
    Member Since
    Oct 01, 2007
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    UK
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    Mac Mini i5 (2014 High Sierra), iPhone X, Apple Watch, iPad Pro 12.9, AppleTV (4)
    The troubleshooting you've done is pretty comprehensive and points fairly strongly to the email account provider and their service.

    If the mail account wasn't configured correctly the mail would remain on the device in the Outbox. If the mail was undeliverable you would receive a notification back. What I suspect is that you provider doesn't allow/work correctly sending from a mobile device. Who's your email provider? Many don't support POP3 on mobile and insist on IMAP.

    To answer your cloud question, iCloud isn't required for email and needs no specific setting etc.

    As a test can you create a new email account. Gmail perhaps, add that and try it?

    Please use the reputation system if you think you've been helped - bottom left of this post

  3. #3

    PGB1's Avatar
    Member Since
    Dec 05, 2008
    Location
    Detroit
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    402
    Specs:
    2007 Mac Book Pro 2.2 Ghz 4 GB RAM SSD OSX 10.11 & 2006 MBP Stuck At 10.6.8
    Thank You for your thoughts & ideas!
    I apologize for not replying sooner.
    It appears I'll have to call the ISP when I can call during daytime hours. The off-hour tech support people could only read the mail settings from a list.

    Hopefully I can call them tomorrow and get results.

    If that fails, I'll try your Google account idea. Hopefully I won't goof up things too badly when I do that....

    I'll post what I find out (hopefully reporting success).

    Paul

  4. #4

    PGB1's Avatar
    Member Since
    Dec 05, 2008
    Location
    Detroit
    Posts
    402
    Specs:
    2007 Mac Book Pro 2.2 Ghz 4 GB RAM SSD OSX 10.11 & 2006 MBP Stuck At 10.6.8
    Very Strange Results Today! And a little progress....

    I tried your good suggestion, Mr Plow, about setting up a GMail account on the iPad and all gmail messages were being delivered to all addresses.
    Now I was more puzzled than ever. Why did gmail send & not the original address, a wowway account?

    This afternoon, I was able to call the ISP for the problem e-mail account that was originally set up on the iPad. I got to talk to someone who wasn't reading from a list. (Yay!)
    She had me change the following-
    A) Change the outgoing server to smtpauth.mail.wowway.com (Per their printed & tech support call instructions, it was smtp.mail.wowway.com)
    B) Change SSL to "Off" (Their printed instructions say "Off" but earlier tech support calls had me turn it to "On".)

    Now e-mail on the iPad is ALMOST 100% working.
    From the iPad I can send to ALMOST any address. I tried sbcglobal.net, gmail.com and wowway.com addresses

    The Strange Part-
    Only messages sent from wowway.com to sbcglobal.net are NOT being delivered.
    Messages from wowway to gmail or another wowway address ARE being delivered.

    Experimentation Form A Computer Revealed-
    Messages from any wowway.com e-mail account on my MacBook Pro (OS X 10.11.6 Mac Mail) to any sbcglobal.net address were also being shown as Sent, but not delivered.
    Messages from any wowway.com e-mail to any gmail or other wowway.com address were being delivered.

    Tech Support's Conclusion
    A) She concluded changing from smtp.mail to smtpauth.mail allowed some e-mail to be sent from the iPad
    B) Sbcglobal is somehow blocking wowway. She said this is as far as she can go, but will send her notes to a higher level tech support to try to find out why sbcglobal is blocking wowway and hopefully get wowway unblocked.

    She also said, quite correctly, that I will not be able to inquire directly to sbcglobal.net to get wowway unblocked.
    When I've had problems with sbcglobal.net e-mail I've been met with results that pretty much say "it's a free address. You're on your own." That's understandable. We originally got these sbcglobal addresses years ago when we signed up for AT&T's DSL as our ISP. Eventually AT&T put them under Yahoo's management & quit supporting them. When we switched to another ISP, they let us keep the sbcglobal.net addresses. (Still under Yahoo control)

    Another Puzzlement
    Wowway's printed pages say to leave outgoing SSL off. Two of my calls to tech support told me to turn it on. The person today said to turn it off on the iPad.
    On my wife's & my MacBook Pro Mac Mail, we have SSL on for wowway.
    I tried SSL on & off on the iPad. Mail sends fine both ways (except for the sbcglobal problem)

    If wowway says leave SSL off and we have turned it on; does SSL encrypt or does wowwway simply ignore the setting & send my messages, address & password unencrypted?

    I'm getting a little frustrated, a lot confused, but at least I'm learning new stuff. Any day one can learn something new is a good day!
    Last edited by PGB1; 12-07-2017 at 07:33 PM. Reason: Fixing typing mistakes. The curse of the dyslexic!

  5. #5

    chscag's Avatar
    Member Since
    Jan 23, 2008
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    Late 2013 27" iMac, 10.5" iPad Pro, iPhone 6s+, iPhone 7+, Numerous iPods, High Sierra
    @Paul:

    If I was a drinking person, I would definitely need several stiff belts after reading your posts. Always interesting reading.

  6. #6

    mrplow's Avatar
    Member Since
    Oct 01, 2007
    Location
    UK
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    Mac Mini i5 (2014 High Sierra), iPhone X, Apple Watch, iPad Pro 12.9, AppleTV (4)
    I think what you're proving conclusively is that wowway's email service is poor/patchy/badly supported.

    In my experience this isn't uncommon for 'bundled' email products from ISPs etc. For many years now I've been de-coupled from bundled email services. They tend to perform poorly and having an independent email service means you can switch ISP with any email change hassle.

    I won't recommend an email provider, different people have different requirements and expectations. But I would strongly suggest it's something to look into.

    Please use the reputation system if you think you've been helped - bottom left of this post

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