Outlook.co.nz sent emails lost with no bounce notification

Forums › Microsoft Windows › Outlook.co.nz sent emails lost with no bounce notification

OldWolf2

23 posts

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#281394 15-Feb-2021 18:40

Sorry if this isn't the right forum, please advise if there was a better place to post.

I had a situation today when sending email FROM the outlook.co.nz web interface ( https://outlook.live.com/owa/ ) . I sent four emails in about a two-minute period: two to my work email address, and two to my gmail. None arrived.

I kept sending test emails; the next one to my gmail did arrive, and everyone after that did arrive successfully -- including exact duplicates of the ones sent earlier that failed to arrive.

There was no bounce notification or anything to indicate that delivery failed. The messages do appear in the "Sent Items" folder.

I had been suspecting this kind of problem existed over the last few months after people unexpectedly failing to carry on email conversations (but maybe could have been explained by them not wanting to talk to me).

I have an address @outlook.co.nz.

Has anyone else had this problem happen to them as well?

Thanks for any possible clues. Not sure if this is relevant, but a few months ago I also had a problem emailing to someone who is with another NZ ISP and getting bounce messages about some technical reason to do with Microsoft incorrectly configuring their email gateways , and a support guy from the target ISP whitelisted my source address. But that was different as I did at least get bounces in that case.

snnet

1410 posts

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#2656938 15-Feb-2021 18:58

I've experienced this not specifically with the outlook service but with outlook (the app) to gmail addresses - I get a bounce back about a week or two later and it's not the normal google bounceback

MadEngineer

4271 posts

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#2656941 15-Feb-2021 19:02

You said the emails sent earlier eventually turned up. Sounds like Grey listing.

You're not on Atlantis anymore, Duncan Idaho.

OldWolf2

23 posts

Geek

#2657078 15-Feb-2021 20:44

MadEngineer: You said the emails sent earlier eventually turned up. Sounds like Grey listing.

They never turned up.

1101

3122 posts

Uber Geek

#2657360 16-Feb-2021 10:31

OldWolf2:

MadEngineer: You said the emails sent earlier eventually turned up. Sounds like Grey listing.

They never turned up.

"and everyone after that did arrive successfully -- including exact duplicates of the ones sent earlier that failed to arrive"]

sounds like they did turn up ?

btw, if blocked/marked as spam/junk , you wont receive any bounce notification .

OldWolf2

23 posts

Geek

#2659794 19-Feb-2021 14:04

1101:

"and everyone after that did arrive successfully -- including exact duplicates of the ones sent earlier that failed to arrive"

sounds like they did turn up ?

By "exact duplicates" I mean two emails having the same title, source and content etc.

It went like this:

* Send message 1 (never arrive)

* Send message 2 (never arrive)

* Send message 3 (never arrive)

* Send message 4 (never arrive)

* Send message 5 (arrive immediately)

* Send message 6 (arrive immediately)

* Send message 7 (arrive immediately)

* Send message 8 (arrive immediately)

and message 7 has the same title , source and content as message 1 (but a later timestamp obviously), and message 8 has the same title, source and content as message 2 (but a later timestamp).

1101:

btw, if blocked/marked as spam/junk , you wont receive any bounce notification .

Is there any way I can check if this happened to an email? It's a deal-breaker really for this provider if a legit email I send can be silently deleted by the server.

MadEngineer

4271 posts

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#2659878 19-Feb-2021 15:30

As above

You’ll find messages 1 and 7, 2 and 8 are the same but delayed.

Greylisting if you’re not aware works by telling a sending email server no but try again later. A real server will do so, a spamming one is a little less likely to do so or in the meantime the spam filter gets updated to learn if the content is likely junk.

The email headers will reflect this.

You're not on Atlantis anymore, Duncan Idaho.

fearandloathing

503 posts

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#2659883 19-Feb-2021 15:35

Try sending an email to https://dkimvalidator.com/; it will give you an idea if your email is being treated by spam filters.

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Delphinus

611 posts

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#2659896 19-Feb-2021 16:18

MadEngineer: As above

You’ll find messages 1 and 7, 2 and 8 are the same but delayed.

Greylisting if you’re not aware works by telling a sending email server no but try again later. A real server will do so, a spamming one is a little less likely to do so or in the meantime the spam filter gets updated to learn if the content is likely junk.

The email headers will reflect this.

OP suggested that 7 and 8 had different timestamps to 1 and 2. My experience of greylisting is the timestamp isn't changed. Ie message 1 (if greylisted) would arrive after message 6, but with an earlier from time.

MadEngineer

4271 posts

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#2659935 19-Feb-2021 17:41

I see a lot of spam coming from outlook services and all it takes is for one server to be blacklisted due to one moron then in future all email originating from that server will be rejected (with notification) or treated as junk (no notification) depending on the recipient's mail server configuration.

What can then happen is a legit sender that's using office365 may find that 1/4 emails get treated as spam due to 1/4 of their emails being sent from that blacklisted server.

Have a look at the headers.

You're not on Atlantis anymore, Duncan Idaho.

Rickles

2933 posts

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#2659943 19-Feb-2021 18:11

@OldWolf2 .... my daughter often sends me emails using her outlook.co.nz address, and they either do not arrive, or turn up anything from 2 hours to 10 hours later!

This has been randomly happening for the last 2 or 3 months

Batman

Mad Scientist
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#2665980 1-Mar-2021 08:02

Outlook has terrible code and lots of bugs.

Here are my encounters

- notification says I have mail but when I go into app it can't find it
- doesn't show other mail that's been stacked
- can't find some mail on app but easily found on webmail

OldWolf2

23 posts

Geek

#2666511 1-Mar-2021 21:39

Batman: Outlook has terrible code and lots of bugs.
- notification says I have mail but when I go into app it can't find it
- doesn't show other mail that's been stacked
- can't find some mail on app but easily found on webmail

Yeah have had all that ... messages disappear and can't be found , etc. Also , stuff that matches my non-junk whitelist being junked anyway (and then when you mark it non-junk it still doesn't sort it). Even had mail rejected by destination ISP, with a bounce response saying Microsoft's server is incorrectly configured .

It seems there's a lot of reason to switch but the alternatives all have issues too:

Gmail having to log into the whole browser and switch accounts just to check email is a PITA (I have a main google account I don't want to use for general email).
My ISP doesn't do email.
If I use my domain name provider's mailbox option it costs extra and they have s**tty mailbox size limits anyway. (Lol what site censores s**t in 2021?) And the webmail interface is 20 years old so very impractical to use from phone.
Smaller providers risk going under or being sold and then I have to do all this again .

The main feature I like about Outlook is being able to seamlessly switch between my phone and my PC (can even start typing something on one device and finish it on the other) . And it doesn't have the problem of receiving mail to one device and then you can't view that mail from any other device, those were dark days.

OldWolf2

23 posts

Geek

#2667982 4-Mar-2021 23:18

Update to my last message. Gmail now makes it easier to have 2 accounts (you can switch account without big deal, and turn off all the google sync crap for the second account). So I've set up one of those.

Also I tried to do some research on email security (SFP, DKIM, DMARC) and I don't think my current domain provider does it correctly for working with Outlook, in fact https://support.office.live.com/en-nz/f1/topic/f4a6107f-6e07-4020-afbb-639fbcf0466f?showContactUsNav=False&ns=OLWACB&version=16 says that support for using your own domain name is completely discontinued unless you have a paid subscription AND you use GoDaddy as registrar, neither of which I do.

NB. The domain isn't the entirety of the problems discussed up-thread as some of my never-arrived emails were not sent through the custom domain. Performance of the custom domain is definitely worse though, I can send from a third party address to my custom domain and to outlook.co.nz directly; the latter arrives immediately and the former takes 10 minutes.

TL;DR multiple issues here that I haven't got to the bottom of, but I'm going to try attaching my domain to protonmail instead, as their help files on this issue fill me with a whole lot more confidence than Microsoft's.