Outlook for Mac - 2017 anomaly

[Unfairly Treated]

Hi,

On 8 February 2017, I encountered a problem where an email with a 40MB attachment from my Hotmail account using Outlook for Mac on my iMac was successfully sent from my end, but it never reached the intended recipient. The email went into my Sent Items folder, but the recipient claims they never received it.

I have considered possible reasons such as file size limits and network interruptions, but I'm still uncertain about the root cause. I want to rule out any anomalies or known issues that might have occurred in Outlook for Mac during that time.

Does anyone recall if there were any known anomalies or software issues in Outlook for Mac in 2017 that could have allowed emails with oversized attachments to go into the Sent Items folder without actually being delivered? I would appreciate any insights or suggestions on how to troubleshoot this issue.

Thank you for your help!

 

[mmkerc]

From 2017 it may be tough to troubleshoot, and from your title is sounds like the recipient and you have some sort of dispute which means it could be tougher.

Initial thoughts are it went to recipient's junk mail, or was too big to be processed, or recipient misfiled the email and does not remember where it was placed.

You can look at your header information on the email. I am not sure how to "read" it but several on the board may be able to help.

 

[Unfairly Treated]

Thanks mmkerc!

I accept the email was blocked somewhere in cyberspace but only after it went into my sent items in Outlook for Mac.

The recipient alleges the email was never sent and that it would have been impossible to do so; however, despite not being very techy, I know it wasn't impossible as I clicked send and it went into my sent items. Microsoft Support confirmed it was possible:

"Since we are not able to replicate what happened with the same circumstances as you had when the email was created, we cannot confirm if what happened was a glitch or if that's how Outlook worked in your version at that time. What we have emphasized is that, it was possible for your email to appear in the Sent folder but was not delivered as it was also confirmed by the email you received from the Postmaster that the delivery failed."

However, this does not explain what the glitches were at the time that allowed this to happen.

I found a chat forum from 2017 which suggested other Outlook for Mac users were having problems at the time:

See the link to a Sync Error Code 17193 chat that I found online: https://community.spiceworks.com/topic/1961948-mac-outlook-2016-sync-error-every-12min

See OP Neogeo174 comment on Feb 2nd, 2017 at 9:40 PM:


“I found it, it was a message in the sent items, deleted it and now the problem is solved.

Thanks for you reply”

and the trail below including markccclure’s comment on Jul 31sr, 2018 at 2:47 PM:

“Same thing has been happening to me. I went into the Sent folder and isolated all of the emails that included attachments. The email in question has a very large attachment that actually sent successfully back in June but for whatever reason was throwing the error. I deleted the email from Sent and 'so far' the error has not reappeared. If anything changes I will report back but as of now deleting the offending email has resolved the issue.”

If you or anyone else knows the actual reason for the anomaly in Outlook for Mac; I should be very grateful if you would enlighten me!

Thanks

 

[chrfr]

Hi,

On 8 February 2017, I encountered a problem where an email with a 40MB attachment from my Hotmail account using Outlook for Mac on my iMac was successfully sent from my end, but it never reached the intended recipient. The email went into my Sent Items folder, but the recipient claims they never received it.

Even today, the attachment sending limit for Outlook.com, which used to be Hotmail, is 25MB. The chances that your email ever sent are pretty slim.

 

[Unfairly Treated]

Even today, the attachment sending limit for Outlook.com, which used to be Hotmail, is 25MB. The chances that your email ever sent are pretty slim.

Hi chrfr.

I not trying to determine whether the email was received, as it appears the email was blocked by Hotmail somewhere in cyberspace but only after it went into my sent items in Outlook for Mac.

The recipient alleges the email was never sent and that it would have been impossible to do so; however, despite not being very techy, I know it wasn't impossible as I clicked send and it went into my sent items of Outlook for Mac. Microsoft Support confirmed that it was possible. I am just trying to identify what the anomaly was that meant the email went into sent items in Outlook for Mac.

 

[chrfr]

Hi chrfr.

I not trying to determine whether the email was received, as it appears the email was blocked by Hotmail somewhere in cyberspace but only after it went into my sent items in Outlook for Mac.

The recipient alleges the email was never sent and that it would have been impossible to do so; however, despite not being very techy, I know it wasn't impossible as I clicked send and it went into my sent items of Outlook for Mac. Microsoft Support confirmed that it was possible. I am just trying to identify what the anomaly was that meant the email went into sent items in Outlook for Mac.

An email with a too-large attachment would still successfully send on your email app. It would have resulted in you receiving a message that indicates that the email you sent was rejected, and the recipient would receive nothing at all. None of this behavior is specific to any email client app.

 

[Unfairly Treated]

An email with a too-large attachment would still successfully send on your email app. It would have resulted in you receiving a message that indicates that the email you sent was rejected, and the recipient would receive nothing at all. None of this behavior is specific to any email client app.

Hi chrfr. What do you mean about receiving a message? After the email went into sent items, I did not receive an email message indicating the email was rejected. This issue appears to be specific to the Outlook for Mac email client app at that time - for example, if you try and send an email with an oversized attachment in Outlook for Mac today a message pops up and says "One or more files could not be attached because they excess the file size limit. Total size of attachments must be less than 33MB." and the email stays in drafts. That did not happen in 2017 - for some reason, I clicked send and it went into sent items. As an IT simpleton, I assumed that because the email was in my "sent items" in Outlook for Mac that it had been sent.

 

[chrfr]

Hi chrfr. What do you mean about receiving a message? After the email went into sent items, I did not receive an email message indicating the email was rejected. This issue appears to be specific to the Outlook for Mac email client app at that time - for example, if you try and send an email with an oversized attachment in Outlook for Mac today a message pops up and says "One or more files could not be attached because they excess the file size limit. Total size of attachments must be less than 33MB." and the email stays in drafts. That did not happen in 2017 - for some reason, I clicked send and it went into sent items. As an IT simpleton, I assumed that because the email was in my "sent items" in Outlook for Mac that it had been sent.

There are really too many variables to say what might have happened, especially 6 years ago.

 

[ThrowerGB]

Hi chrfr. What do you mean about receiving a message? After the email went into sent items, I did not receive an email message indicating the email was rejected.

Unfairly Treated:

1. You say you "did not receive an email message indicating the email was rejected" yet in your 6:02 AM post you quote Microsoft Support as saying "as it was also confirmed by the email you received from the Postmaster that the delivery failed." It seems to me that these two statements are inconsistent. However MS Support may have misinterpreted what you told them, or simply assumed incorrectly that you had received a message from the Postmaster. In other words, I think you've given us two statements that are inconsistent with each other, and that makes it very difficult for us to help.
2. I can't see anything in what you wrote that explicitly confirms your or recipients recollection of what happened over 6 years ago. You say you're an IT simpleton. Please don't be so hard on yourself. The situation you describe, where there's uncertainty about everything that might have happened is very common, and also quite hard to analyze. Usually we're left with just speculation. I'll give you some of my speculation.
3. I think chrfr has written some considered responses and s/he seems to be experienced in the the processes involved with email.
4. There is a chain of multiple steps involved after you hit the send button and the recipient receiving that email. Those steps include things like:
   1. determining what steps are required for your system to send your email. Here, when I say send, I mean the email software you are using.
      1. for example, your email may have a size limit. Size limits of 25 MB and 33MB are referred to in this thread. They may be for different steps in the chain.
      2. if a limit is reached, some systems separate oversize attachment(s) and send them using non-email to a repository the receiver can access. I don't have much experience with that except for just a couple of cases over many years where I was receiving an email with encrypted and secured attachment (I think it was from an insurance company). It took me a long time talking with several support teams to figure out how to get the attachment. I may have initially told the insurance company I hadn't received the attachment.
      3. sorry for rambling here.
      4. if everything on your end is good, your system sends the email package(s) from your symptom and places it in your sent folder. But it can also wait until the next level mail system, be it Google, Hotmail, Yahoo, iCloud, or Gmail, etc. acknowledges before it tells your PC email software it can be treated as sent. Your email moves through the internet to other email servers, each of them may have different processes, rules and limits. Sometimes either they or the domain name servers and/or routers that comprise the internet get overloaded or hacked, and sometimes messages just get lost.
      5. eventually your email reaches your receiver's email server. That's a system that usually lives in the background of the internet and not on your PC. It may have different processes, rules and systems, and the message can be rejected for a variety of reasons. Usually it will send you an email message saying so. Over the years, those rejection emails have become more and more user friendly. They used to be very cryptic! At this stage, on your PC, your email should be in your Sent folder, but might not yet have reached your recipient's PC software. I'm describing this in a very summarized way. As email systems have evolved, there are more and more checks with messages going back and forth within the long chain, to make the system more robust, able to handle more traffic, deter hackers, etc.
      6. After the email is received by your recipient's email software on their PC, it is dealt with by a variety of processes and usually ends up in your email inbox.
5. But things can go wrong. One of these example may have happened to you:
   1. A rejection message coming back to you may be regarded as Junk by the software on your PC, and it might be lost, never reaching your Inbox.
   2. Several types of email systems have evolved over time.
      1. An older version is POP where the email is simply passed to your PC and stored there. If you have email software on your phone and your PC, the first one that accesses your email provider's server(s) will receive it but your other devices won't.
      2. A newer version, IMAP, stores the emails on your email providers servers. It stays there, available to each of your devices, until one of your devices deletes it, and it might go to Trash, or Junk on each of your devices.

At this point, if I were you, and if someone says they didn't receive an email you sent, I'd try to figure out what happened to it, as you've been doing. Perhaps you can find explicit proof that they did receive it, but possibly not. Perhaps you have a copy and can resend. It's generally fruitless to argue whether or not they did receive it, because often explicit proof doesn't exist. Some systems such as doctor's portals store emails they send and receive on their own portals. You can log in to their portal and read it or download. This is a much more secure way to handle email. The doctor can be assured that you've actually read the email, and the email remains private between you and the doctor, in compliance with HIPAA (the Health Insurance Portability and Accountability Act).
If your email was important like providing important information to a mortgage lender. It's a problem, and you'll need to find a mutually agreed remedy, if you can. But if what's lost is something that doesn't matter, shrug your shoulders and move on.

I apologize for my bluntness and long-windedness. I'm aware I may have offended you, for which I also apologize. But I hope what I've written is useful to you.

 

[chown33]

It's possible that a message informing you of an undeliverable message was treated as spam by your email app, and deleted without your knowledge.

I mention this because it used to be common to send fake "bounce messages" to random recipients, often with malicious attachments, saying "Your message could not be delivered. Please open the ZIP file for details."

Here's a lengthy description of bounce messages:

Bounce message - Wikipedia

en.wikipedia.org

Some diagrams there are informative, because it shows how any delivery agent along a chain can fail with a bounce message. It also shows that email delivery isn't nearly as simple in practice as the basic concept might seem. There's a whole lot of stuff going on behind the scenes.