Weird email issue

A friend and his wife are having an email issue that leaves me scratching my head.

She has an ipad and a gmail account; he has a verizon.net email account.

For whatever reason, when they're at home (fios wifi) her emails don't deliver to his account when using the ios mail app. If she uses google's gmail app (which she hates) messages deliver fine. She had a stroke a year ago and doesn't take change well anymore; she wants to use just the ios mail app.

They asked at some shops, but coulnd't replicate the problem: At both the apple store and the verizon store, the ios mail client delivers fine on store wifi. At a local microcenter, it delivers mail fine. Using my phone as a hotspot, it delivers mail fine. Reconnect the ipad to the fios wifi, it won't deliver.

There doesn't appear to be anything unusual in either the ios mail settings or the fios router settings.

Any ideas?

-jk

Some ISPs block out going SMTP email on port 25. It looks like Verizon is probably one of them:

https://kevinlawry.wordpress.com/2010/06/10/verizon-fios-blocking-smtp-port-outgoing-email/

You can probably fix it by changing the port that the iPad is using to send email, probably to port 465 or 857, which are typical ports supported when the ISP blocks port 25.

I should have explicitly said that it's only when she sends to her husband's email that it's a problem. Everyone else gets mail.

I haven't tested against other verizon.net accounts, though...

-jk

Perhaps the email address in her contacts entry for the husband is incorrect, or there is more than one.

If she replies to husband email message using iOS does it also fail in the same way?

Is there any error during or after attempted email sending from iOS to husband?

I've seen this happen with incorrect DNS setup, but highly doubt that's the case here.

If it was the email address that was wrong then the email wouldn't fail dependant on what network it was connected to.

There's just one, correct entry. I even deleted and re-entered it.

Replies also fail.

I've since learned she can email a different verizon.net address just fine.

-jk

That's where I was headed. But now I can't figure how one verizon.net mailbox works and another doesn't if it's a dns issue.

If I hadn't seen it, I'd be skeptical.

-jk

And you're absolutely certain that the same email address is being used, and it works on one network and doesn't work on the other?

Very interesting. If you haven't already, I would investigate to see if spam filtering is the culprit. Maybe the recipient has a spam filter that is triggering on multiple factors, one of which is the network from which the email originated.

Do the outgoing iOS email messages appear in the Gmail web interface as sent mail, even if they do not ever arrive at husband's inbox?

If iOS is successfully getting the sent email out of the iPad and into the Gmail system, then the subsequent message loss/diversion would be somewhere downstream, no?

Have you verified that the messages are not getting stuck in the iPad's outbox?

What Tony said.

Also, try using a 3rd party mail server and see if that makes a difference (even better if it's on a server where you can access the mail logs.)

This too. However I would think that the messages would pour out once the machine transitions to the other network.

What happens when there are additional recepiants?

Do the others receive their copies, while the problem address fails?

Along this path, check to see if their home internet IP address is blacklisted. Verizon's servers might be seeing the IP on one of these blacklists and silently dropping the message. These two sites cover most of the common spam blacklist services.

http://mxtoolbox.com/blacklists.aspx

http://www.spamhaus.org/lookup/

That's what was puzzling me about this. If the mail simply didn't send, I would think a backlog would go out as soon as the device connected to another network.

DNS shouldn't explain why other addresses work, but it's worth a shot. It shouldn't be too hard to switch her iPad or router to Google's DNS or one of the others in order to test this.

When you say it doesn't deliver, does she get a notice that delivery failed? Or is the email just disappearing?

Is it possibly getting delivered, but marked as spam? Does the husband have any email filters set up?

Yes, it's definitely the same email address - both from the address book and when manually entered.

I'll test with multiple addresses. I have confirmed a different verizon.net address does indeed work.

I'll check spamhaus, but it's only one address so I'm thinking it's unlikely.

There is no indication of delivery failure on the ipad. The ios mail app doesn't put messages in the sent items, you have to bcc yourself. She receives her bccs.

All good ideas. I'll do a little more poking around.

thanks!

-jk

What's weird here, I think, if I'm understanding your description correctly:

- His email address is a Verizon.net address.
- The delivery failure occurs when she's on the Verizon.net FIOS wifi connection.

If I'm understanding it correctly, that's the situation in which the message should arrive with the best chance of being received: With most of the middlemen cut out.

So, though your descriptions seem to indicate that it's getting spam-binned on his end, I'm wondering why the same messages from OUTSIDE the verizon network don't get spam-binned.

I don't have a clue how email is handled anymore. It baffles me.

I may have posted about this before, but I have to send snail mail invoices to any of my clients who use AOL. I use Freshbooks for my invoicing, and AOL has completely blocked anything I send to their users. I haven't even had luck emailing a PDF from my own email account.

Nevermind that every time I see the inbox of an AOL user, it's chock full of obvious spam.

It wouldn't bother me as much if my emails were getting flagged as spam. That would be fine, as I could simply tell my client to look for my email in their junk folder. But no, they're wiping out my email before it ever reaches their customers. I find that offensive, considering the obscene garbage that fills most people's spam folders. Unless it's abundantly clear that a message is spam or contains a virus, it makes me furious that an email provider would fail to deliver a message like that. It's not just AOL either. To bring things back to Verizon, I've had this happen with a couple of my clients who use their Verizon mail.

Quick question: have you logged into this person's webmail? I seem to recall that some Verizon email accounts are essentially Yahoo mail accounts. I've always had the most difficulties with those accounts when setting them up in mail programs. I can't think of how it would cause the issue you're seeing, though...