Personal emails going to other people's spam folders

skybox44 · 2 May 2025, 10:09 AM

I struggle with my emails from personal email addresses going to the spam/junk folders of other personal email addresses. It happens across all my email addresses with different providers. Outlook, Gmail, Yahoo, it doesn't matter. I'm in school and professors often don't respond to my emails, but sometimes they'll respond after a long time and say they didn't see my email until they checked their junk folder. I've tested it out by sending emails to myself (from my gmail to my outlook, my yahoo to my outlook, my gmail to my yahoo, etc etc) and very often, my emails will end up in the spam folder.

I don't know why. I guess there are many potential reasons, but I'm a computer dumbie, and I get overwhelmed when I look up advice online. Most of the advice out there is for professionals trying to increase the deliverability of their marketing emails and newsletters. To make it clear: I'm talking about individual emails, sent from one individual account to another. I rarely ever have even more than one person copied on an email. So I'd like to get advice that's geared to these concerns. But, if any of the techniques people use to increase marketing email deliverability could also apply to me, I'll try them. Even if they are paid services.

The reason I'm trying to figure this out now is that I want to send an important email in the next few days that I do not want to wind up in spam. So it's important to me to find some solution to this now.

Where do I start? Should I use some service like email warmup? Talk to a deliverability consultant? Get my own domain? Please explain like I'm five, because as far as these things go, I might as well be.

TenFour · 2 May 2025, 12:12 PM

What email service are you using to send your emails from? If Gmail, are you using a regular personal Gmail account so your address ends in @gmail.com? Are you using the official Gmail app on your phone or the official Gmail Web app?

skybox44 · 3 May 2025, 02:02 PM

Quote:

Originally Posted by TenFour

What email service are you using to send your emails from? If Gmail, are you using a regular personal Gmail account so your address ends in @gmail.com? Are you using the official Gmail app on your phone or the official Gmail Web app?

I use gmail, yahoo, and outlook, and run into problems with all of them. When I use Gmail, yes I use a regular account ending in @gmail.com. I usually use the official Gmail site on desktop or the official site on mobile browser (Safari). I don't use the app.

The main one I want to work is outlook. That's the one I use for school. I have a personal one that ends in @outlook.com, and another that ends in the school domain. I have problems with both of them, but the school account is the most important.

TenFour · 4 May 2025, 04:31 AM

It sounds like it may be the IP address you are sending from, or else something odd with the setup of your personal email addresses. But, I have experienced the situation where within an organization we were all on the same Microsoft 365 account and yet our own emails to each other would end up in Junk no matter what we did. Microsoft email is notorious for false positives on Junk email to the point I make it part of my daily routine to check the Junk folder for important emails.

Can you experiment with someone you know by sending test emails from your various personal addresses and seeing if there is a pattern?

JeremyNicoll · 4 May 2025, 04:51 AM

Do you mostly post these troublesome mails from within 'school' (by which I assume you mean a college or university)? If so, maybe your posting IP address (presumably within the college/university's cabled/WiFi network) has some relevance? It'd be easy for such addresses to have gained a bad reputation (from activities of other users).

Most (if not all) mail providers add headers to incoming mails which provide hints - not always all that easily understood though - which say why they thought mails were good, or spammy.

In the first place you need to look at the headers inside the experimental mails you sent from one of your personal addresses to another, and see for each provider what hints these mails contain. Even within a single provider's arriving mails, the spam-scores might not be precisely the same in all such mails, as the software which does this adapts to changing threats, and of course reacts differently to differing mails' contents.

Subsequently you might need to ask other people (to whom you send mails which their systems class as spam) to zip entire mails up & send the zips back to you for you to analyse. But the majority of your recipients are probably using the same systems as you, so solving the issues in your test mails should go a long way to fixing problems elsewhere.

I suggest you read through the recent Fastmail-specific spam-scoring discussion (in a subforum here) at:

http://www.emaildiscussions.com/showthread.php?t=80912

as it might give you some clues. (Fastmail is a paid-for provider, & clearly the discussion is about what they put into mails arriving on their system, but they use a popular tool - Spam Assassin - to do it, as do many other providers.) NB: providers are able to tweak SA to include/exclude specific tests, and I think to apply differing weights to them, so two providers seeing the same mail on the same day would not necessarily score them the same.

Once you've done so, and looked at headers in your test mails, maybe you will be able to identify which spam tests are contributing the most points towards your mails' spam scores.

Feel free to post portions of spam-score headers here (but make sure none contain your personal information) for further help.

SideshowBob · 12 May 2025, 09:49 PM

When you send from webmail there isn't, by default, any information about the sender's address or network because the mail client is the webserver. It used to be common to add the source IP address in a dedicated header, but that seems to have gone out of fashion - these days the information tends to be encrypted or at least obfuscated.

2 May 2025, 10:09 AM	#1
skybox44 Junior Member Join Date: May 2025 Posts: 7	Personal emails going to other people's spam folders I struggle with my emails from personal email addresses going to the spam/junk folders of other personal email addresses. It happens across all my email addresses with different providers. Outlook, Gmail, Yahoo, it doesn't matter. I'm in school and professors often don't respond to my emails, but sometimes they'll respond after a long time and say they didn't see my email until they checked their junk folder. I've tested it out by sending emails to myself (from my gmail to my outlook, my yahoo to my outlook, my gmail to my yahoo, etc etc) and very often, my emails will end up in the spam folder. I don't know why. I guess there are many potential reasons, but I'm a computer dumbie, and I get overwhelmed when I look up advice online. Most of the advice out there is for professionals trying to increase the deliverability of their marketing emails and newsletters. To make it clear: I'm talking about individual emails, sent from one individual account to another. I rarely ever have even more than one person copied on an email. So I'd like to get advice that's geared to these concerns. But, if any of the techniques people use to increase marketing email deliverability could also apply to me, I'll try them. Even if they are paid services. The reason I'm trying to figure this out now is that I want to send an important email in the next few days that I do not want to wind up in spam. So it's important to me to find some solution to this now. Where do I start? Should I use some service like email warmup? Talk to a deliverability consultant? Get my own domain? Please explain like I'm five, because as far as these things go, I might as well be. Last edited by skybox44 : 2 May 2025 at 10:26 AM.

2 May 2025, 12:12 PM	#2
TenFour Master of the @ Join Date: Feb 2017 Location: USA Posts: 1,953	What email service are you using to send your emails from? If Gmail, are you using a regular personal Gmail account so your address ends in @gmail.com? Are you using the official Gmail app on your phone or the official Gmail Web app?

4 May 2025, 04:31 AM	#4
TenFour Master of the @ Join Date: Feb 2017 Location: USA Posts: 1,953	It sounds like it may be the IP address you are sending from, or else something odd with the setup of your personal email addresses. But, I have experienced the situation where within an organization we were all on the same Microsoft 365 account and yet our own emails to each other would end up in Junk no matter what we did. Microsoft email is notorious for false positives on Junk email to the point I make it part of my daily routine to check the Junk folder for important emails. Can you experiment with someone you know by sending test emails from your various personal addresses and seeing if there is a pattern?

4 May 2025, 04:51 AM	#5
JeremyNicoll Cornerstone of the Community Join Date: Dec 2017 Location: Scotland Posts: 565	Do you mostly post these troublesome mails from within 'school' (by which I assume you mean a college or university)? If so, maybe your posting IP address (presumably within the college/university's cabled/WiFi network) has some relevance? It'd be easy for such addresses to have gained a bad reputation (from activities of other users). Most (if not all) mail providers add headers to incoming mails which provide hints - not always all that easily understood though - which say why they thought mails were good, or spammy. In the first place you need to look at the headers inside the experimental mails you sent from one of your personal addresses to another, and see for each provider what hints these mails contain. Even within a single provider's arriving mails, the spam-scores might not be precisely the same in all such mails, as the software which does this adapts to changing threats, and of course reacts differently to differing mails' contents. Subsequently you might need to ask other people (to whom you send mails which their systems class as spam) to zip entire mails up & send the zips back to you for you to analyse. But the majority of your recipients are probably using the same systems as you, so solving the issues in your test mails should go a long way to fixing problems elsewhere. I suggest you read through the recent Fastmail-specific spam-scoring discussion (in a subforum here) at: http://www.emaildiscussions.com/showthread.php?t=80912 as it might give you some clues. (Fastmail is a paid-for provider, & clearly the discussion is about what they put into mails arriving on their system, but they use a popular tool - Spam Assassin - to do it, as do many other providers.) NB: providers are able to tweak SA to include/exclude specific tests, and I think to apply differing weights to them, so two providers seeing the same mail on the same day would not necessarily score them the same. Once you've done so, and looked at headers in your test mails, maybe you will be able to identify which spam tests are contributing the most points towards your mails' spam scores. Feel free to post portions of spam-score headers here (but make sure none contain your personal information) for further help.

12 May 2025, 09:49 PM	#6
SideshowBob Essential Contributor Join Date: Jan 2017 Posts: 332	When you send from webmail there isn't, by default, any information about the sender's address or network because the mail client is the webserver. It used to be common to add the source IP address in a dedicated header, but that seems to have gone out of fashion - these days the information tends to be encrypted or at least obfuscated.