email being sent to me being bounced and emails going to Junk folder even though I have marked them as OK

Address each symptom separately, starting with checks that are under direct control in Outlook/Outlook.com.

1. External senders getting bounces

• Ask the senders to confirm the exact bounce message and whether it mentions spam, reputation, or throttling. The error “Unable to deliver message after multiple retries, giving up” usually indicates a delivery or routing problem on the sending side or along the path, not in the Outlook client.
• For Outlook.com or Outlook on the web mailboxes, verify that the senders’ addresses and domains are not on the Blocked senders list:
  • Sign in to Outlook.com or Outlook on the web.
  • Go to Settings > Options or Mail.
  • Open Blocked senders or Block and allow and remove the sender/domain if present.
• If the senders still cannot deliver after confirming their systems are healthy, ask them to contact Microsoft via postmaster.live.com as described in the Mail section of the Mail and Calendar guidance.

2. Messages still going to Junk after being marked “Not junk”

• First, explicitly add the sender or domain to Safe senders:
  • In Outlook.com/Outlook on the web: Settings > Mail > Junk email.
  • Under Safe senders and domains, select Add safe sender, enter the email address or domain, select OK, then Save.
• Also check that the sender or domain is not on the Blocked senders list in the same Junk email settings page. If it is, remove it.
• In the Outlook desktop client, open Junk Email Options and verify:
  • The sender is not on the Blocked Senders tab.
  • If using the Safe Recipients List, confirm the group or address is present if that is how the mail is addressed.
• If using a Samsung or similar mobile device with a built‑in mail app, check the device’s spam list:
  • Open the email app on the device.
  • Go to Settings > General Settings > Spam addresses.
  • Remove any legitimate addresses or domains (for example, your own domain) so the device does not push those messages into Junk.

3. Messages only appear after restarting Outlook

• This behavior is typically client‑side. Since messages arrive after restarting Outlook, the mailbox itself is receiving mail, but the client is not refreshing correctly.
• Check for hidden or misconfigured rules that might be diverting mail:
  • In Outlook, open Rules and review all rules, including any that move items to RSS feeds or other folders. Disable or delete suspicious rules.
• If using Mail and Calendar for Windows 10 or Outlook on the web in parallel, also review any rules or blocked senders there, as server‑side rules apply to all clients.
• If a specific address is missing messages, verify it is not in any blocked list as above.

If, after these checks, mail is still misrouted or missing, sign in to Outlook.com/Outlook on the web directly and observe where new messages arrive. If they appear correctly there but not in the Outlook desktop client until restart, the problem is isolated to the client profile or sync and should be escalated with Outlook client troubleshooting (profile repair, update, or reinstall).

References:

• Mail goes to the Junk folder by mistake
• New email messages automatically move to the Junk folder in Microsoft Outlook
• Filter junk email and spam in Outlook
• Where are my email messages or calendar events in Mail and Calendar for Windows 10?
• Options > Junk Email
• Outlook.com doesn't send any emails to junk folder - Microsoft Q&A