Can’t Forward A Specific Email From Outlook

HDL · Sep 13, 2022

Windows 11 ver. 21H2 (OS Build 22000.856)

I’m not looking for a fix for this problem, although that would be great if you know of one, because all I have contacted convinced me it can’t be fixed. It is just what it is. I find that hard to believe. I’d settle for an explanation as to why it is happening if anyone can give me that. I’ll try my best to describe what steps I have taken, all with the same results – I cannot forward a specific email.

My wife and I use the same ISP’s email server- Spectrum Webmail - with email addresses ending with neo.rr.com. I receive emails each month and had been forwarding them to her. The specific email is a Discover Card statement. The statement I just received, I forwarded to her and asked that she look into the charges. I sent it 4 time to her, and she never received it. I then learned she has never received any of the statements I have forwarded to her for the Discover Card statement.

In the past I had setup a Gmail account for her and it forwards emails to her neo.rr.com account. Now the steps I took trying to get this email to reach her.

1. I sent it to her 4 times using Outlook, none even reaching her ISP’s WEBMAIL server. I was signed into it watching to see if it did.
2. I sent and forwarded other emails and they all reached her neo.rr.com account.
3. I called our ISP’s support. He had me send an email from my WEBMAIL server to her email account and it reached her. He was trying to blame Outlook. He concluded there was nothing wrong and wanted me to contact Microsoft.
4. I called the fellow who builds my computers, and he has experienced this same problem but had no solution. His problem was with a digital receipt from a membership store. He said he couldn’t even forward it to himself into another of his email accounts.
5. I sent this statement to her Gmail account it reached that account but would not forward it to her neo.rr.com account.
6. I forwarded other emails to her Gmail account, and it forwarded everyone of them to her neo.rr.com account.
7. I contacted Discover’s technical support. She tried to brush me off with a nonsense explanation believing I’d fall for it. Her explanation was that my wife’s email server probably would not accept emails from Discover or me. We both have the same email server, only with different sign in credentials. This support person couldn’t seem to understand that.
8. I gave up

Any ideas why this is happening. Again, if you have a solution, that would be great. But if not, even an explanation would be appreciated.

Thanks

Berton · Sep 13, 2022

Can you send a plain text message to her with no attachment, no forward? Have you tried saving the attachment as a file then send a message to her including that file? Can you send any other file such as an image to her as an attachment? Can you send the message with attachment to yourself or you with a different E-Mail address? I have ended up with more addresses than I need now, one [and my wife's] is my primary service as part of hosting my Domain, one is provided by my ISP, one is Hotmail.com from late '90, one is Outlook.com [not the installed Microsoft Outlook program], one is Gmail and one is a custom at Mail.com. All are free except the first one. A good one for an extra is SeaMonkey browser which includes E-Mail. The Outlook.com Webmail was intended to merge Hotmail.com and both have now ended up as outlook.live.com.

HDL · Sep 13, 2022

Berton said:
Can you send a plain text message to her with no attachment, no forward? Have you tried saving the attachment as a file then send a message to her including that file? Can you send any other file such as an image to her as an attachment? Can you send the message with attachment to yourself or you with a different E-Mail address? I have ended up with more addresses than I need now, one [and my wife's] is my primary service as part of hosting my Domain, one is provided by my ISP, one is Hotmail.com from late '90, one is Outlook.com [not the installed Microsoft Outlook program], one is Gmail and one is a custom at Mail.com. All are free except the first one. A good one for an extra is SeaMonkey browser which includes E-Mail. The Outlook.com Webmail was intended to merge Hotmail.com and both have now ended up as outlook.live.com.

The answer to your questions are all yes. Now the mystery may have just been solved. I have no idea why this would happen or how it is even possible. None of the emails that were sent with the word discovery in them either as the statement itself or an attachment in the form of a Word document got to her WEBMAIL server yesterday. When I signed into it today it still did not appear in the Inbox but everyone of them was in the Spam folder. They were not there yesterday. So I marked each of them NOT SPAM and sent a new email just now. It put it into the Spam folder again instantly. I am going to have to call the ISP and see how I make the WEBMAIL server recognize these email as not Spam permanently and allow them to go into the Inbox.

Maybe the WEBMAIL was not working correctly yesterday because I know there was nothing in Spam or Junk folders.

HDL · Sep 13, 2022

Just got off the phone with Spectrum's support who's WEBMAIL server is used for both my wife's and my accounts. She had no explanation why this was happening. There were 8 other emails that ended up in my wife's Spam folder in the WEBMAIL'S server that should not have been there. I marked them as Not Spam and will deal with them if they ever end up in the Spam folder again. To "fix" my problem she added my email address to what Spectrum calls a "Safe Sender List." I am able to send that Discover statement to her. Before all this, everything I sent her, she received so there is no explanation why the statement did not get to her.

Berton · Sep 13, 2022

That is a weird situation. I failed to ask but how large is the file involved?

HDL · Sep 13, 2022

Berton said:
That is a weird situation. I failed to ask but how large is the file involved?

It is small, only 43 Kb.

Everything about this is weird but I especially find it very strange that the emails I sent yesterday did not appear in the Spam folder at the time I sent them. Neither the support person I talked to yesterday saw them, and neither did I. There were 8 files in that folder yesterday and today when I discovered the emails I sent ended up in the Spam Folder, I moved them to the Inbox after marking them as Not Spam. The same 8 files remained in the Spam folder. I asked my wife which of these 8 emails she wanted to receive. She said all of them. So I marked them as Not Spam and will have to see if they ever end up in the Spam Folder again. If so, I'll have to add them to the Safe Sender's List too.

johnlgalt · Sep 13, 2022

3 possible reasons.

1) She accidentally marked an email from them that you had forwarded as SPAM (and I mean truly accidentally, as in they was trying to open it and it was flagged as junk, and she didn't realize it).

2) The Roadrunner servers themselves were flagging it as suspicious behavior because you were forwarding from the correct email address to a different one and there was security on the contents that was preventing this (unlikely, as you already said that email forwarded to GMail also was not forwarding from GMail to her account - but still a remote possibility because that forwarded email still has the same security that your cc company put on the email).

3) Your ISP mail server was automatically flagging because of the key word you used - also highly unlikely, as you were receiving the emails in the first place.

It really sounds like something weird happened and those emails were at one time flagged as spam and so subsequent emails met the filter rules and were auto marked as Spam.

As for the email not showing up in the Spam folder immediately, not all email showing in a spam folder is immediate- particularly depending upon the scanning methods used by the email server. That is entirely normal to occur.

HDL · Sep 13, 2022

johnlgalt said:
It really sounds like something weird happened and those emails were at one time flagged as spam and so subsequent emails met the filter rules and were auto marked as Spam.

I am almost certain no one ever flagged these as spam. certainly it was not my wife or I. So my wife doesn't even know how to sign into the WEBMAIL server and even if somehow she accidentally marked it as spam it would only have been affected in her Outlook client, not the WEBMAIL server, as far as I know. Plus remember she never once got any of the statements I forwarded to her.

johnlgalt said:
The Roadrunner servers themselves were flagging it as suspicious behavior because you were forwarding from the correct email address to a different one and there was security on the contents that was preventing this (unlikely, as you already said that email forwarded to GMail also was not forwarding from GMail to her account - but still a remote possibility because that forwarded email still has the same security that your cc company put on the email).

I can't even begin to speak of what Road Runner could have done but I did just go and add her Gmail address to the safe Senders' list. So, if it works as it should, Gmail should now forward it to her in the future. I did not test that since making the change.

johnlgalt said:
Your ISP mail server was automatically flagging because of the key word you used - also highly unlikely, as you were receiving the emails in the first place.

Yes this does seem unlikely. Here is something that may make it even stranger, not sure. When I forwarded these statements to her, the subject was just, "You Have A New Statement," the same as it came to me. That's all, no mention of Discover or any other company.

johnlgalt · Sep 13, 2022

HDL said:
I am almost certain no one ever flagged these as spam. certainly it was not my wife or I. So my wife doesn't even know how to sign into the WEBMAIL server and even if somehow she accidentally marked it as spam it would only have been affected in her Outlook client, not the WEBMAIL server, as far as I know. Plus remember she never once got any of the statements I forwarded to her.

Only true if Outlook is using POP - if IMAP or Exchange server, it will be on the server, not just in Outlook.

HDL said:
I can't even begin to speak of what Road Runner could have done but I did just go and add her Gmail address to the safe Senders' list. So, if it works as it should, Gmail should now forward it to her in the future. I did not test that since making the change.

No worries- evne they can't speak as to what they do sometimes. lol

HDL said:
Yes this does seem unlikely. Here is something that may make it even stranger, not sure. When I forwarded these statements to her, the subject was just, "You Have A New Statement," the same as it came to me. That's all, no mention of Discover or any other company.

Ahhh, my mistake, I thought you mentioned something about the subject line stating Discover. So, it was quite literally something like

FW: You have a new statement

There has to be something really different going on - if it was from Discover's end, 1) they'd already know about it and would have told you, and 2) it never would work, even now. I don't know of anything like that that can target only a single email address and not allow forwarding. Makes no sense, as you've noted.

Check all the rules and blocked domains in her outlook settings, too.

HDL · Sep 14, 2022

johnlgalt said:
Only true if Outlook is using POP - if IMAP or Exchange server, it will be on the server, not just in Outlook.

Yep it is a POP server. Not that I want an IMAP server but I can't get one with my ISP, Spectrum, if I wanted to. I am told I am a legacy customer and cannot get the IMAP. This was back about 9 months ago when I found out this one program I purchased was sending out notifications of an update I was entitled to. I was not getting the notifications. Turns out that company uses Zendesk for these notifications and Zendesk quit sending anything to my Road Runner domain because they would always bounce back for anyone who used neo.rr.com. Had to give them my Gmail account to get the notifications. I called Spectrum, they took over my Road Runner account a few years ago, and was told what I mentioned, I am not eligible to set up an IMAP account.

johnlgalt said:
Check all the rules and blocked domains in her outlook settings, too.

Already did, at least as far as I know how to do. Also the Spectrum "help" person was supposedly doing that also between putting me on hold for most of our time on the phone. I am monitoring her WEBMAIL server to make sure she gets all the emails she wants to get. Hopefully, I can get this all sorted out soon. Thanks for your help.