Outlook email delivery problem

Nataša Keser 0 Reputation points
2026-10-12T21:58:09.6933333+00:00

Hello,

I've been experiencing recurring email delivery issues with my Outlook account.

Some recipients report that they haven't received my emails, while others find them in their spam folders.

Additionally, I've noticed that replies from people with whom I've already exchanged numerous emails sometimes end up in my Junk Email folder, even though our previous correspondence was delivered normally.

These issues have been happening repeatedly and are affecting my professional communication.

I would like to speak with a technical support agent and have my account checked for any possible sending restrictions, spam filtering issues, or other problems with incoming and outgoing email delivery.

Could please somebody help me with this.

Thank you for your assistance.

Outlook | Web | Outlook.com | Email
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  1. AI answer

    2026-10-12T21:58:29.5666667+00:00

    For an Outlook.com account, these are the supported checks to do first:

    1. Sign in to Outlook.com on the web and verify where messages are going.
      • Check Junk Email, Other, Deleted Items, Archive, and any custom folders.
      • Check Filter > Sort > Date so messages are not just appearing out of order.
    2. Review settings that can redirect or hide mail.
      • Check whether email forwarding is enabled.
      • Check whether any email rules are moving or deleting messages.
      • Review Junk Email settings and the blocked senders list.
    3. For messages that recipients do not receive:
      • Check whether the message generated a non-delivery receipt and read the reason.
      • If the recipient address is wrong or the domain changed, correct the address and resend.
      • If the recipient mailbox is full, the recipient must reduce mailbox size.
      • If the error mentions blocked, spamcop, dynablock, blackhole, or spamhaus, the recipient’s email provider has blocked the sending source. In that case, the recipient’s provider support team must unblock it.
      • If the error is can’t connect to remote server, message expired, or connection timed out, wait a short time and resend.
      • If the message is undeliverable, make sure the recipient address is valid, reduce the number of recipients, and if the message was sent from Outlook or another mail app, try sending it from Outlook.com.
    4. For messages going to spam or junk:
      • Ask recipients to add the sending address to their safe senders list.
      • Add frequent contacts to Contacts in Outlook.com.
    5. If sending fails in Outlook.com:
      • Remove any signature from the message and try again.
      • If there is an attachment larger than 25 MB, Outlook.com cannot send it.
      • If the account is newly created, a temporary low sending quota can apply until the account establishes credibility.
    6. To reach Outlook.com support:
      • In Outlook.com, select Help on the menu bar, enter the issue, then scroll to Still need help? and select Yes.
      • If self-help does not solve the problem or sign-in is not possible, use the Outlook.com support entry point provided in the support article.

    If the issue is specifically that replies from known correspondents are landing in Junk Email, the supported checks are the Junk Email settings, rules, forwarding, and whether the messages were filtered into Other or another folder.

    AI-generated content may be incorrect. Read our transparency notes for more information.

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  2. Manoel Barros 22,250 Reputation points Independent Advisor
    2026-10-12T23:59:18.78+00:00

    Hi!

    1. Is your email personal, corporate, or educational?
    2. Is your email from your custom domain (@yourname.com, @companyname.com), Microsoft (@outlook.com or @hotmail.com), Google (@gmail.com), or a third-party domain?

    If you use Outlook Web, you are using either a Microsoft account or a custom domain from a provider that uses Microsoft's email services. In any case, it is important to know this information.

    Additionally, do the senders you exchange emails with belong to the same company or group, or do they share the same custom domain?

    Is there anything in common among the senders with whom you experience this issue (for example, attachments)?

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