Share via

550 5.4.316 Message expired, connection refused

Dorothy Thompson 25 Reputation points
2026-04-06T19:29:51.5033333+00:00

Just for the past week or so, I have been unable to get messages delivered to a friend who I've been able to email without issue for many years. Friend’s email provider said: Ask your friend to contact her email provider with the same error and tell them: “The recipient uses a @charter.net address and can receive from others and from me using a different account. Please investigate why your outbound server can’t deliver to Charter (550 5.4.316 Message expired, connection refused).”

Outlook | Web | Outlook.com | Email
0 comments

2 answers

Sort by: Most helpful
Most helpful Newest Oldest
  1. Chloe-V 7,265 Reputation points Microsoft External Staff Moderator
    2026-04-07T09:00:38.68+00:00

    Hi Dorothy Thompson,

    Welcome to Microsoft Q&A forum. 

    Please follow the steps that Q&A Assist suggested first. If the issue isn’t resolved, or if you run into any problems while trying them, please let me know so I can help further.

    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. 

  2. Q&A Assist
    2026-04-06T19:30:02.5733333+00:00
    AI generated content. This question contains an answer created with AI from Q&A Assist. Learn more

    The error 550 5.4.316 Message expired, connection refused indicates that the Outlook.com outbound servers repeatedly tried to connect to the recipient’s mail system (Charter) but could not, so the message eventually expired and was returned as undeliverable.

    For Outlook.com, this falls under the category of “Can’t connect to remote server/message expired” or “Connection timed out” delivery failures:

    1. The problem is typically transient network or server connectivity between Outlook.com’s outbound servers and the recipient’s provider.
    2. The message may succeed later without any changes on the sender side.

    Recommended actions based on Outlook.com guidance:

    1. Wait and resend
      • Wait some time (for example, a few hours) and resend the message.
      • If the non‑delivery report (NDR) indicates the recipient’s provider will keep retrying, no action is required until it either succeeds or fails definitively.
    2. If the problem persists over multiple days
      • Since the recipient can receive from others and from a different account, the issue is likely specific to the path from Outlook.com to Charter.
      • In that case, the only supported path is escalation via the providers:
        • The sender should keep the full bounce message (including headers and the 550 5.4.316 text).
        • Contact Outlook.com support through the standard support channel in Outlook.com and provide the full error so they can investigate why their outbound servers cannot deliver to Charter.
        • The recipient can also contact Charter support and provide the same NDR so Charter can check if Outlook.com servers are being blocked or rate‑limited.

    If a delivery failure message from Outlook.com instead mentions being “blocked” or “listed in” a blacklist service, the resolution would be to contact the recipient’s provider to request unblocking. However, for a pure message expired/connection refused scenario, the primary steps are to retry later and, if ongoing, have both providers investigate using the full NDR details.

    References:

Your answer

Answers can be marked as 'Accepted' by the question author and 'Recommended' by moderators, which helps users know the answer solved the author's problem.