This usually comes down to a broken connection between the client and the mail server. First, check your internet connection — open any website to confirm it's working. Then go to Send/Receive and hit Update Folder. If the message is stuck, try moving it back to Drafts, deleting it, and composing it again. A corrupted email with a very large attachment can also block the entire outbox queue.
If messages from others aren't arriving, check your Junk Email folder first — filters sometimes catch legitimate senders. Then verify your storage quota under Settings > General > Storage. A full mailbox silently rejects incoming mail. Also confirm that no forwarding rules are accidentally rerouting everything elsewhere.
When login keeps failing, the usual suspects are:
Slowly loading or completely missing attachments are often a browser cache issue when using the web version. Clear your cache, or try an incognito window. In the desktop app, check that your antivirus isn't scanning and blocking outgoing attachments in real time — some AV tools intercept mail traffic and cause timeouts.
If calendar events aren't showing up across devices, the sync interval may be set too long. On mobile, go to the account settings and set the sync frequency to Every 15 minutes. On desktop, a corrupted OST file can cause persistent sync failures — rebuilding it by removing and re-adding the account usually fixes it.
Outlook's local search index can fall behind, especially after a large mailbox migration. Go to File > Options > Search > Indexing Options and rebuild the index. On the web version, search issues are server-side and typically resolve within a few hours on their own.