Outgoing outlook.com emails going into spam folders

Question

Outgoing outlook.com emails going into spam folders

Simon Lockwood 15

When i send outlook.com emails i'm not sure they are received as sometimes im told they are found in junk / spam. I do not receive a bounce email, so i don't know either way - and sometimes i only have an email address so have no other way to check. I use the app mainly and occastionally web mail and iOS mail. I don't know if it is using all of these or just the app. This is for fresh emails, not forwarding dodgy looking content. Sometimes its just my CV.

Help!

2 answers

Your answer

Answer 1

Winnie-B 6,035 Microsoft External Staff Moderator

Hi Simon Lockwood

Thank you for reaching out to Microsoft Q&A Forum. I understand how frustrating it is when your emails end up in recipients’ spam folders even though you don’t get any bounce‑back.

Here are some steps that you could try:

1. Check your message content

Normal emails can be flagged if they include:

Many links
Attachments sent repeatedly
Very short subjects, or no subject

Try sending a few test emails with a simple subject and without attachments to see if they get delivered normally.

2. Send from Outlook on the web to test

Go to https://outlook.live.com and try to compose a new email there to see if the issue persists.

3. Ask your recipients to mark your messages as safe

Sometimes the receiving mail service suddenly tightens filtering. Ask a few people you email regularly to:

Open your email
Click Not Junk (or Mark as safe)
Add your address to Safe senders and domains

For more details, you can see these support links:

Please feel free to let me know how it goes. I truly appreciate your time and understanding!

If the answer is helpful, please click "Accept Answer" and kindly upvote it. If you have extra questions about this answer, please click "Comment".

Note: Please follow the steps in our documentation to enable e-mail notifications if you want to receive the related email notification for this thread.

Winnie-B 6,035 Reputation points Microsoft External Staff Moderator

2026-02-20T06:56:44.77+00:00

Good day Simon Lockwood, I hope you're well. May I know if you've got any chance to check my reply? If you have any further updates on this issue, please feel free to reach back. I'm happy to help you.

Additionally, for important applications, please try using Outlook on the Web via https://outlook.live.com exclusively for a week to see if delivery improves compared to the iOS or mobile app.
Simon Lockwood 15 Reputation points

2026-02-20T07:41:54.9433333+00:00

@Winnie-B

Thank you. The challenge is that this is a business context so i can't really engage with the recipient like this. And i still don't know if there will be a problem with a new recipient, it might go through fine. When you say "attachments sent repeatedly" do you mean from me broadly rather than multiple times to one recipient? I've sent my CV multiple times, so i could do a small update and change the file name for the next version. I'm still sending around once per day though, if that. And my first email to a recipient is with no attachment (which be seen as spam). I'll make sure there are no links and there's a subject.

Simon
Winnie-B 6,035 Reputation points Microsoft External Staff Moderator

2026-02-22T06:41:23.9333333+00:00
Hi Simon Lockwood

Thanks for your update. About vary attachments and filenames when sending your CV, reusing the same attachment file name and structure across multiple recipients can contribute to filtering. Updating the document slightly and changing the file name, as you suggested, is a good approach. Also, please try following this:

Use a consistent and clear subject line

Avoid very short or generic subjects

Use a descriptive subject that matches the email content

Avoid signatures or formatting that looks promotional

Keep formatting simple

Avoid images, banners, or repeated blocks of identical text

Review your Sent items regularly

Even without bounce messages, consistent delivery from the same interface can help identify patterns over time.

Thank you for your understanding.
Ian-T 7,465 Reputation points Microsoft External Staff Moderator

2026-02-23T10:29:56.1833333+00:00

Hi Simon Lockwood

I’m following up to check on the status of this issue.

Have you had an opportunity to review the answer shared earlier?

Any update you can provide would be greatly appreciated.
Simon Lockwood 15 Reputation points

2026-02-23T14:44:07.9866667+00:00

@Ian-T thanks but it was only yesterday that i had the latest advice. I shall follow this advice, but of course, i don't know if im hitting spam filters or not when im sending to people that i dont know well enough to check via other channels.
Winnie-B 6,035 Reputation points Microsoft External Staff Moderator

2026-02-25T05:20:19.4866667+00:00

Hi Simon Lockwood

Thank you for your clarification. Please feel free to go ahead and follow those steps for now. I understand that it’s difficult to confirm whether messages are hitting spam filters when sending to new recipients, so monitoring the behavior over a bit of time is the best next step.

Thank you for your understanding. Have a good day!
Simon Lockwood 15 Reputation points

2026-02-27T14:15:55.7633333+00:00

Hi @Winnie-B

Would it be fair to say that if there has been a succesful back and forth of emails with a specific recipient, that should mean that new replies should go through ok (one longer email chain)? Thanks
Winnie-B 6,035 Reputation points Microsoft External Staff Moderator

2026-03-01T04:41:14.99+00:00

Hello Simon Lockwood

Thanks for your response. In general terms, having a successful back‑and‑forth with a recipient does improve the likelihood that replies in the same chain will be delivered normally, but it does not fully guarantee it. Each message is still evaluated individually by the recipient’s mail system, especially when attachments or content change.

Answer 2

kagiyama yutaka 1,165

I think the snag is those shared outlook.com IPs… sometimes you get one that’s been beat up before you. one plain‑text mail first—no sig, no links usually lets their filter calm down. sorry it’s a crude fix, but it’s saved me more than once.

Simon Lockwood 15 Reputation points

2026-02-17T12:40:42.85+00:00

Thanks. I'll try that sometime. Sadly, i'm using for job hunting, so a random blank email may not look so professional (ie might look like ive just pressed send at random), but worth bearing in mind.
kagiyama yutaka 1,165 Reputation points

2026-02-19T04:29:19.8033333+00:00

yeah I get that… for job apps u can’t just fire a blank mail. what’s worked for me is sending a tiny clean opener and one line, no links, no sig then drop the real CV mail right after. keeps the spam filters from freaking out, even if it’s not the prettiest fix.
Simon Lockwood 15 Reputation points

2026-02-19T09:19:19.18+00:00

Thank you. The challenge is that this is a business context so i can't really engage with the recipient like this. And i still don't know if there will be a problem with a new recipient, it might go through fine. When you say "attachments sent repeatedly" do you mean from me broadly rather than multiple times to one recipient? I've sent my CV multiple times, so i could do a small update and change the file name for the next version. I'm still sending around once per day though, if that. And my first email to a recipient is with no attachment (which be seen as spam). I'll make sure there are no links and there's a subject.

Simon
kagiyama yutaka 1,165 Reputation points

2026-02-19T09:46:11.7266667+00:00

Thank u for letting me know, i get it… in a biz setting that “light first mail → then the attachment → quick follow‑up” flow can be pretty hard to use.

when i said “repeatedly” i just meant that this kind of step‑by‑step send has helped me with filters before. if i’m off, sorry ...really hope ur mails land clean.
Simon Lockwood 15 Reputation points

2026-02-19T10:01:45.9566667+00:00

Thanks @kagiyama yutaka I posted my comment incorrectly - it was for the microsoft team's comment. I appreciate your help.
kagiyama yutaka 1,165 Reputation points

2026-02-19T10:21:06.4466667+00:00

your welcome Simon Lockwood

Thanks

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Outgoing outlook.com emails going into spam folders

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