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

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?

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

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!

@Paul:

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

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.

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.

That's great idea!
We should start switching over soon. Once done, it will make any changing of ISPs much less tedious!


I think what you're proving conclusively is that wowway's email service is poor/patchy/badly supported.

My wife and I often joke when the television, e-mail servers, phone or internet go out (at least one each day). We just look at each other & say "It's Amateur Hour". Maybe they're like the Little Engine That Could-- Trying & trying, but haven't quite succeeded yet.

I have "uncoupled" my email address from any ISP by using a forwarding service. It also blocks spam pretty well. In my case, I use pobox.com for the service. What happens is I give out my "public" email address as [email protected], they then receive the mail and filter for spam then forward to my "real" email address that IS provided by my ISP. Every once in a while my "real" address slips out and eventually spammers start getting past the spam filtering, which forces me to change mail services for the real address. But when I change ISPs, all I have to do is tell pobox to change from the old to the new and all my mail moves over from that instant on. Nobody has to change anything and I don't have to send out any changes. The charge from pobox for this service is very reasonable, I think US$15/year. I don't have any financial interest in Pobox, just want to put it out there as an option. (You also get three aliases for that fee, which is interesting sometimes because I'll give one of them as the "registration" email for those sites that insist on an email to register, but if I start getting spammed at that alias, I'll go to pobox and change the alias to something else, which means all that spam ends up in the bit bucket.)

That's a neat way to keep mail addresses under control, Jake. Thanks for sharing it. I never knew such forwarding services existed & will look into it further. I like the added bonus of some spam control.
Thanks, too, for your good explanation of how this works. I appreciate your help & idea!
Paul

@Paul:

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

Click to expand...

I imagine if you're still involved Charlie, you must be pretty blotto by now. :Blushing:


@Paul

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.

Click to expand...

I didn't notice it being mentioned, but a good way to test an email message working properly is to send a new message from the user's email account to the same user's email account.

If it's not working, a dialog note should/may show saying what is wrong. If it is working, the sent mail will show up in short order, or should.




- Patrick
======

Thanks Patrick for the tip.
Sending from the account to the account works. It appears that only problem remaining is sbcglobal is not delivering mail from wowway addresses. (Computer & iPad)
As a sort of redundant test, I set up an appointment in Calendar app & had an e-mail notification sent from a wowway address to a sbcglobal address. It did not get delivered. Reversing it worked.

Sbcglobal must be blocking wowway. Trying to contact them was unproductive. The ISP (wowway) said they would also try. A call back to them had no notes, so they probably didn't do anything.

Not sure what my next step will be.

Not sure what my next step will be.

Click to expand...

Maybe try some of the mail server tests you can find with a search such as:
test mail server
https://www.google.ca/search?client...F-8&gfe_rd=cr&dcr=0&ei=R1s1WuTcK9LM8geviqrgCw

Can you setup a new "more normal" email account to use or at least for testing???

And have you at least tried the “Test account settings” that seems to be available according to this page:
https://www.sbcglobalattmail.com/sbc-global-net-pop3-settings/

PS: Getting settings correct can be a real PITA frustrating experience. i.e.: a large local ISP some years ago said settings should be as they said on their web page, but they wouldn't work properly for Mac users for some odd reason. A friend tech discovered the solution was to use a specific port number, NOT the one recommended, and then things worked. The type of "authorization" used and setup can also be a source of problems and using Mail is not always the easiest to setup at times it seems.

Anyway, just some thoughts for you to try…




- Patrick
======

Hello Patrick & Thanks For The Ideas.

I've tried many tests of the server via 3rd party and by sending messages back and forth. Other than from wowway.com addresses, sbcglobal.net addresses are receiving. (For example, Reply notifications from mac-forums are delivered to a sbcglobal.net address.)

"Test Account Settings" mentioned on https://www.sbcglobalattmail.com/sbc-global-net-pop3-settings/ for sbcglobal does not seem to exist anywhere on the pages, nor while logged into sbcglobal.net.

I don't know what constitutes a "more normal" e-mail account, but I have sent many successful messages to and from non-sbcglobal addresses- like gmail.

When sending to a sbcglobal.net address, wowway shows successful delivery to the recipient, but the mail never actually gets to the recipient. The mail definitely completely leaves the computer and gets all the way to Yahoo (handler for sbcglobal.net). Yahoo is not delivering it.

I have logged into each of our sbcglobal.net accounts and checked for spam settings or for any blacklist capability. There is nothing blocking wowway addresses in the accounts, so I am guessing it is system wide that sbc~ blocks wow~.
Buried way deep in the web pages I found a place to send a request to 'whitelist' and address. The request is handled by a person, therefore not automatic, so I may or may not see any results from my request.

To Summarize Testing To Date-
(Tested on 3 devices. One is OS X 10.6.8, one is 10.11.6, one is iOS Tested using 4 different sbcglobal.net addresses & 4 wowway.com addresses)
Mail from any address ending in wowway.com will be delivered to any recipient except one ending in sbcglobal.net
Mail ending in sbcglobal.net can receive any message from anyone except an address ending in wowway.com

This Makes Me Think-
Our mail is set up properly on both sbcglobal.net and wowway.com for incoming and outgoing.
Wowway is sending mail past their server to the intended destination.
Sbcglobal.net is blocking only wowway.com addresses. (Of course, I don't know if this is just our addresses or if they block all wowway.com mail)

The Challenge-
Get Yahoo to let mail from wowway through.

Thanks Again for helping with this!
Paul

The Challenge-
Get Yahoo to let mail from wowway through.

Thanks Again for helping with this!
Paul

Click to expand...

Very odd and very frustration for you Paul, and maybe some expert in tracking or whatever can come up with a solution.
I would expect the techs at the ISP that you pay good money to to be doing something to help.




- Patrick
======

Thanks, Patrick!
Unfortunately, the ISP isn't helpful. Last week, I called and the technician said she believed sbcglobal (Yahoo) is blocking wowway and she would send it to someone to investigate. Today's call showed they had no notes on the subject & no information. I pretty much was given the "Oh Well" treatment.

I'll keep trying to find a solution. When more time permits, I'll try to get up the ISP technical support ladder farther. Every call to the ISP is at least 45 minutes before someone is speaking, so it may be a day or two until I can hold still long enough to call again.

Thanks, Patrick!
Unfortunately, the ISP isn't helpful.

Click to expand...

That sounds like a big understatement.

I'm no expert in that stuff, but what about just setting up a new email account like with Apple (with your Apple ID) or even gmail.com and use it?

I'd sure be surprised if neither of those two email accounts didn't work properly.

And maybe save yourself a lot of exasperation and give yourself a nice Christmas present — an email address that actually works properly.

PS: I assume that you have checked for any goofy account settings and made sure no blocking/spam delete filters or preferences are actively messing things up???





- Patrick
======

pm-r said:

That sounds like a big understatement.

...what about just setting up a new email account like with Apple (with your Apple ID) or even gmail.com and use it?

I'd sure be surprised if neither of those two email accounts didn't work properly.

PS: I assume that you have checked for any goofy account settings and made sure no blocking/spam delete filters or preferences are actively messing things up???


- Patrick
======

Click to expand...

I've got a couple of gmail accounts that work great and play well with others (the wowway and sbcglobal accounts), so I'm pretty well convinced the problem is that sbcglobal is blocking wowway or wowway has some problem that sbcglobal does not like- perhaps a certificate they don't approve of (wild guess). The problem is, wowway blames sbcglobal & sbcglobal is unreachable.

I never thought of having an Apple e-mail account until you mentioned it and didn't know one could do that. If any e-mail account should work properly, that's got to be the one!

You are & others here are right, it is time that we replace these e-mail services (both wowway and sbcglobal) with something more reliable.
Perhaps the best bet is something like gmail, a forwarding service like the one Jake mentioned earlier or the Apple ID associated e-mail you mentioned.
As an added bonus, when I switch ISPs when the white coat people take to the insane asylum (because too many ISP problems finally sent me over the edge), I'll be able to keep my e-mail addresses.

As an added bonus, when I switch ISPs when the white coat people take to the insane asylum (because too many ISP problems finally sent me over the edge), I'll be able to keep my e-mail addresses.

Click to expand...

Yup, you got it. And have something that actually works. Very satisfying!!!

PS: If you wanted to spend and maybe waste some time checking on any current blacklist status etc., you could try some of the tests at places like this:
https://www.whatismyip.com/blacklist-check/




- Patrick
======

Thanks Patrick!
The blacklist checking sites were interesting to explore (Code for "goof around on"). My domain didn't show up as a bad guy, so I suppose it is a problem isolated to Sbcglobal versus Wowway.
Maybe one or the other of the two domains will fix the problem (Yeah, sure...)

Note... the "Blacklisted" sites that show up on the IP search list are those that sponsor or allow spammers to use. Our forum software checks those sites on demand and can "ban" single or a range of IP addresses. I highly doubt your ISP would be on that list as they would not stay in business very long.