Friend with Yahoo account suddenly getting blocked by my Hotmail account

KSav

KSav

Post hoc Beatlemaniac
Location
Northern Plains
I hope someone can help me with this, because I'm not having a lot of luck online: All the articles I've found focus on business contexts, and this is personal.

I've had a pen pal in a different country (Australia, in case that helps) for more than 5 years. That entire time, he's been using a Yahoo email address and I've been using Hotmail. There have been no problems (well, except for my own emails going directly to his spam folder about once every 10–12 months) until the past few weeks, when his emails have been getting returned as undeliverable with a Mail Daemon message.

It seems to be getting worse: I woke up this morning to an email from him that he said he'd tried to send twice yesterday with no success. I'm not sure why, all of a sudden, this is an issue. I have added him to my contacts, so this issue further confuses me.

I actually have several email accounts, for various reasons, including with Outlook, Gmail, and Zoho Mail. However, Outlook is just the rebranded version of Hotmail and uses the same servers, and I don't think Gmail and Zoho Mail provide desktop notifications, which means I'd have to constantly be checking my inbox.

Just thought I'd throw this out here in case anyone has any ideas.
 
Good ol' AI says this:

If a Yahoo Mail account suddenly starts blocking messages from a Hotmail (now part of Outlook), it’s usually not random—something triggered the spam or safety filters. Here are the most common reasons:

1. Spam filtering got stricter
Yahoo may have flagged recent messages from that Hotmail address as spam. This can happen if:
  • The emails look repetitive or promotional
  • They contain lots of links, attachments, or certain keywords
  • Other users marked similar messages as spam
2. The sender’s reputation dropped
Email systems track sender reputation. If that Hotmail account:
  • Sent a lot of emails quickly
  • Got reported by recipients
  • Was compromised or used for spam
    Yahoo may automatically block it.
3. Authentication issues
Modern email relies on checks like SPF, DKIM, and DMARC. If something changed on Microsoft’s side (or the sender’s configuration), Yahoo might not trust the messages anymore and block them.

4. User-level filters or accidental blocking
The Yahoo user might have:
  • Accidentally marked one message as spam
  • Added the Hotmail address to a blocked list
  • Created a filter that sends those emails to trash
5. Content changes in emails
Even normal senders can get blocked if their email suddenly includes:
  • Suspicious links
  • Attachments (especially uncommon file types)
  • Formatting that resembles phishing emails
6. Security triggers
If Yahoo detects anything that looks like phishing or spoofing (even falsely), it may start blocking that sender automatically.


 
Thanks, @CallMeKate ! The situation is actually the opposite: My Hotmail account is blocking his Yahoo account. However, I would think the information you provided works both ways.

I did just add him to my safe sender list, which I'd assumed he was already on because I have him added as a contact.

At least the messages are getting returned to him, so he knows they're not getting through. Every 10 months or so, one of mine will go directly to his spam folder, with no notification to either of us. (Now that's frustrating.)
 
GoodEnuff said:
Outlook/Hotmail have changed. I have had so many problems even logging in that I gave up.
Click to expand...
Yes, I'm close to giving up on Hotmail. I just recently set up an Outlook account for my work activities, and it was such a hassle with all the vendors, etc. that I'm reluctant to go through that again. But I'm close to it.
 
GoodEnuff said:
Outlook/Hotmail have changed. I have had so many problems even logging in that I gave up.
Click to expand...
Outlook/Hotmail stinks!
I still have an account, years ago I used to pay for it.

@KSav you may need to contact Hotmail to see if they can resolve the issue.
Or use a different e-mail.
I use Pop Peeper e-mail notifier for my 4 accounts. You can use it for free or pay to get extra things.
There is also a way to put a yahoo/gmail e-mail on your desktop if you are interested.

How to Create Shortcuts to Websites on your Desktop​


There is an easier way to do it, let me see if I can find that.

🤗
 
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Hotmail / Outlook is my primary email and causes me a host of problems. Setting up a Proton email may be one workaround for you. It's free, easy, and doesn't require 2 step authentication. I don't recommend it for all uses, since some websites, services, and companies do not accept Proton Mail addresses, but it would most likely work to correspond with your friend.
 
I found it, works for any website.

Drag and Drop
Open your preferred browser and navigate to the desired website.
Drag the padlock or globe icon located to the left of the URL in the address bar and drop it onto your desktop.
This creates a shortcut that opens the site in your default browser.

Hint;
Look at the website address, to the immediate left of the site address is the ICON you drag to the desktop.

🤗
 
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I don't understand why y'all are having trouble logging in. I've had no issues with that. Also had no issues with email addresses being blocked.
 
I forgot to say:
If you clear your cookies in your web browser,...when you click on your desktop shortcut, you will need to log back into your e-mail or sites like this Forum.

🤗
 
MarciKS said:
I don't understand why y'all are having trouble logging in. I've had no issues with that. Also had no issues with email addresses being blocked.
Click to expand...
I don't understand your post.. no one is having problems logging in.
It is an issues with Ksav's friend being blocked in his Hotmail.

🤗
 
MACKTEXAS said:
Hotmail / Outlook is my primary email and causes me a host of problems. Setting up a Proton email may be one workaround for you. It's free, easy, and doesn't require 2 step authentication. I don't recommend it for all uses, since some websites, services, and companies do not accept Proton Mail addresses, but it would most likely work to correspond with your friend.
Click to expand...
Thanks, @MACKTEXAS! I have two Gmail accounts and a Zoho Mail account, plus a Proton Mail one, so if adding him to my Safe Sender list doesn't work, I'll switch to one of those.

It's past 11:30 pm there right now, so I told him I added him to my Safe Sender list and asked him to keep me posted.

It's odd, though: He'd already been added as a contact. Why aren't all contacts automatically added to the Safe Sender list? :unsure:
 
MarciKS said:
I don't understand why y'all are having trouble logging in. I've had no issues with that. Also had no issues with email addresses being blocked.
Click to expand...
I'm not having trouble logging in. His emails aren't being blocked, they're being returned as undeliverable. But he keeps trying and they eventually do get through.
 
Thank you, everyone, for the replies; I am so appreciative! I'm in a bit of a rush right now and can't tag everyone individually, but if you replied, then THANK YOU. :)

I am hoping adding this person to my Safe Sender list will solve the issue. As I mentioned, I assumed that because he is a contact he was also a Safe Sender.

If his emails keep getting bounced back to him I'll switch to one of my other accounts. I'm just lazy and set in my ways. 😆
 
KSav said:
Thanks, @MACKTEXAS! I have two Gmail accounts and a Zoho Mail account, plus a Proton Mail one, so if adding him to my Safe Sender list doesn't work, I'll switch to one of those.

It's past 11:30 pm there right now, so I told him I added him to my Safe Sender list and asked him to keep me posted.

It's odd, though: He'd already been added as a contact. Why aren't all contacts automatically added to the Safe Sender list? :unsure:
Click to expand...
Because it is my opinion only.. Outlook/Hotmail stinks!
:LOL:
 
KSav said:
Why aren't all contacts automatically added to the Safe Sender list? :unsure:
Click to expand...
I don't know. For 13 years, in my Hotmail (Outlook) I've been on a group email list of one person who sends a daily inspirational email to all of us. About a year ago, I suddenly stopped getting her emails, so I sent her an email to ask if she had removed me, and my email bounced back as undeliverable. I then went to my Yahoo email and tried emailing her again. That one reached her and she replied that I was still on her list.

For whatever reason, some days later - or maybe a week or two - I started again receiving her emails (in Hotmail / Outlook) and have been receiving them ever since.

When I search ChatGPT regarding current issues with Outlook, I get this (there was more):

outlook.jpg
 
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