Skip to content
(731) 798-8625 | After-hours emergency help — call

Outlook or Windows Mail that will not send or receive email is one of the most common calls I get, and it is almost never as bad as it feels when the messages stop coming. Most of the time it comes down to a handful of simple causes, and a few of them you can check yourself in about ten minutes.

What is probably going on

Email programs like Outlook and Windows Mail are just messengers. They log in to your email account over the internet, pick up new messages, and drop off the ones you write. When they stop working, one of those pieces broke. Here are the usual suspects:

  • Your internet or Wi-Fi is down or flaky. The email program gets blamed, but the real problem is the connection.
  • The program lost your password. This happens after you change your password on the email company's website, or after an update.
  • Your mailbox is full. Many free accounts have a storage limit, and once you hit it, mail stops coming in.
  • The program is stuck in offline mode. Outlook has a setting that quietly tells it not to connect.
  • A message in the Outbox is jammed. One big attachment can hold up everything behind it.
  • The account settings are out of date. This is common with older accounts from internet providers.
  • Security software or a recent Windows update is getting in the way.

None of that means your computer is ruined or your emails are gone. Your messages live on the email company's servers, not just on your PC.

Check this first: is it your email or your internet?

Before you touch any email settings, open a web browser and visit a site you do not normally use, like a news page. If it will not load, your internet is the problem, not Outlook. Restart your router by unplugging it for thirty seconds and plugging it back in, then give it a few minutes to come back.

If the internet works fine, go to your email provider's website (Gmail, Yahoo, Outlook.com, or your internet provider's webmail) and log in there. This one test tells you a lot:

  • If webmail works and you can see new messages, your account is healthy and the problem is in the program on your computer.
  • If webmail will not let you in, the problem is with the account itself, such as a wrong or expired password, a locked account, or a full mailbox.

Please do not skip this step. It saves a lot of guessing.

Try this first: a short checklist

Work down this list in order. Stop as soon as mail starts flowing again.

  1. Close and reopen the program. Fully close Outlook or Mail, wait ten seconds, and open it again. Better yet, restart the whole computer.
  2. Check for offline mode in Outlook. Click the Send/Receive tab. If the button that says Work Offline looks pressed in or highlighted, click it once to turn it off. Also look at the bottom right corner of the Outlook window for words like "Working Offline" or "Disconnected."
  3. Open your Outbox. In the folder list on the left, click Outbox. If a message is sitting there, open it, and either delete it or copy the text and attachment somewhere safe first. A stuck message with a large photo or file often blocks everything else.
  4. Press Send/Receive manually. In Outlook, click Send/Receive All Folders. Watch for any error message and write down the exact words, because they help a lot.
  5. Re-enter your password. If you see a password box popping up again and again, type your current password carefully. In Windows Mail, go to Settings (the gear icon), then Manage Accounts, click your account, and choose Change mailbox sync settings or re-sign in if it asks.
  6. Check your mailbox storage. Log in to webmail and look for a storage bar or a note saying the mailbox is full. Delete old messages and empty the Trash and Spam folders, then try again.
  7. Run Windows Update. Click Start, then Settings, then Windows Update, and install anything waiting. Restart afterward.
  8. Try the other app. If Outlook is acting up, try signing in through the Windows Mail app or webmail. If one works and the other does not, that points at the program, not your account.

If you are on a Mac, the idea is the same. Open Mail, click Mail in the top menu, then Settings, then Accounts, and make sure your account is checked and shows as online. If it says offline, go to the Mailbox menu and choose Take All Accounts Online.

Things that look scary but usually are not

A few messages make people panic, so let me ease your mind on them.

  • "Your password is incorrect" even though you are sure it is right. Often the email company changed a security rule, and the program needs to sign in again, or it needs an app password. This is common with Gmail and Yahoo.
  • "Cannot connect to server" or a certificate warning. Usually the connection dropped or a setting is out of date. Do not click through a certificate warning you do not understand, but do not assume you were hacked either.
  • Sent mail coming back as undeliverable. Read the message. Most of the time the address was typed wrong.

One thing to be careful about: if you got an email or pop-up telling you to call a number or click a link to "fix your email," do not do it. That is a common scam. Real email problems do not come with a phone number on a pop-up.

When to stop and call

It is time to stop poking around and get help if any of these sound like you:

  • You have tried the steps above and nothing changed.
  • You are being asked for passwords you do not remember and cannot reset.
  • Outlook will not open at all, or it crashes right away.
  • You are afraid of losing old messages, contacts, or a big attachment.
  • You think someone else got into your account, or you are sending spam you did not write.

This kind of problem is a good fit for remote support. You let me connect to your computer over the internet while you watch the screen, and I sort out the settings with you right there. The remote session is $49, usually under an hour, and it is no fix, no fee. Call or text me at (731) 798-8625, or book a callback and I will get back to you. I help folks in Lexington, Jackson, Parsons, Henderson, and all over West Tennessee, and remote help works anywhere in the U.S.

If the real trouble turns out to be in the house, like a router that keeps dropping out or a computer that will not start, and you are in Henderson or Madison County, in-home repair may be the better route.

How to keep it from happening again

A few small habits keep email running smoothly:

  • Write down your email address and password somewhere safe, or use a password manager, so you are never locked out.
  • Clean out your mailbox every few months. Delete old attachments and empty the Trash.
  • Keep Windows and Outlook updated, but restart your computer after updates finish.
  • Know how to reach your email on the web. If the program ever fails, webmail is your backup and lets you keep working.
  • Do not ignore password prompts. If your program keeps asking, sort it out right away instead of clicking Cancel.

Common questions

Will I lose my old emails if I fix this?

Almost never. Most email accounts keep your messages on the provider's servers, so the program on your computer is just a window into them. I always check that before changing anything, and I will tell you if something needs to be backed up first.

How much does it cost to have someone fix my email?

My remote support session is $49, usually under an hour, and if I cannot fix it, you do not pay. After-hours emergency remote help is $89. Both are done over the internet, so you do not have to go anywhere.

My email works on my phone but not on my computer. What does that mean?

That is actually good news. It tells us your account and password are fine, and the problem is in the program or settings on the computer. That usually makes it quicker to fix.

Need Help?

Got a question after reading this? Give us a call — we're happy to help explain anything or take care of your computer problem.

Get Free Tech Tips

Simple, plain-English tech tips delivered to your inbox. No spam, ever. Unsubscribe anytime.

Ready for help? We make it easy.

No tech knowledge needed. We're friendly, patient, and we speak plain English.