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I Can't Send Email

Chances are your biggest email woes will come when you try to send email. Sometimes Windows Mail will refuse to send email, and it will just sit in your outbox.

There are a few reasons why this might happen:

  • Your outbound email server is offline.
  • Your outbound email server address is incorrect.
  • Your outbound email server requires authentication or you have to check inbound email first to trigger the outbound mail server.
  • Your ISP won't let you send email through a third-party SMTP server.
  • The attachment on your email is many megabytes in size and you lose the connection or the server times out before it can be sent.

Are You Online?

First things first, check to see whether you have a good Internet connection. If you can receive mail and surf the Web with your web browser, you know this isn't an issue.

If your connection is intermittent because it's wireless or unreliable, consider switching to a wired or more reliable connection (if possible) to eliminate a bad connection as the source of your problems.

Is Your Outbound Server Address Correct?

Check to make sure your SMTP server address is correct. Your ISP can provide this server address. Mine starts with SMTP, as in smtp.everyone.net (see Figure 9.37); however, yours may be a variation on that. Your SMTP server could be mail.your-isp.com or smtpX.your-isp.com, where X is a number or another word.

Figure 9.37

Figure 9.37 Check to make sure your SMTP server address is correct.

Check Server Authentication

In a bid to avoid misuse of their servers by spammers, some ISPs require that you log in to their outbound server before sending email. If this is the case, be sure that Windows Mail is set up to do that. Here's how:

  1. Go back into your Email Account by clicking Tools, Accounts, and then selecting your email account and clicking Properties.
  2. Click the Servers tab, and then under Outgoing Mail Settings, check My Server Requires Authentication and click the Settings button.
  3. In the dialog box that opens, you have two choices, and the first is Use the Same Settings As My Incoming Mail Server. If your email provider requires you to authenticate your outbound server, this is the most likely setting (see Figure 9.38).
    Figure 9.38

    Figure 9.38 If your sent email is stalled in your outbox, your outbound email server might require authentication.

  4. If you are using an SMTP server affiliated with a different company than the company from which you get your inbound email (rare, but possible), or your email provider asks you to use a different username and password, you'll need to choose Log On Using and specify a different username and password affiliated with that server.

Is Your Attachment Too Big?

Hey, I'm not being dirty here. I am talking about file attachments. If you thought otherwise, you're a dirty monkey.

So let's get back on track here. If you are sending an outbound email, and it is stuck in your Windows Mail outbox, it could be jammed because of the file attachment. Large attachments can cause havoc with SMTP servers. Often they will time out before an email can be sent, especially if you have a slow Internet connection.

I don't recommend that you send attachments bigger than about 5MB, and even something that large can cause problems on a slow connection (see Figure 9.39). Plus, the recipient will hate you for clogging her inbox. You don't want to annoy grandma the day she is baking pies.

Figure 9.39

Figure 9.39 Don't be a weenie and send big honking email attachments or your friends will hate you.

Also, consider this: If you send a too-large attachment to a person with an account on a corporate server, the server might trash the whole email and attachment or clog the account. So, try not to send that YouTube video of your uncle falling out of a canoe to your Wall Street pal, because it might clog his inbox and result in him missing a million dollar email from Donald Trump. Yep, your attachments could destroy someone's career.

Instead, use a service like YouSendIt.com to transfer big files.

Modify Your SMTP Port Number?

If your outbound email stays in your outbox and won't budge, it could be because you use an email provider that is not the same as your Internet service provider. ISPs don't like you using an SMTP server other than their own.

There are two remedies for this. One is to use your ISP's SMTP server as your outbound email server (and authenticate as necessary) or change the default port for outbound email.

Most ISPs expect you to use port 25 for your SMTP server, and so they block any activity on that port unless you're using their SMTP server. You can get around this, however, by using a different port. Some email providers let you communicate with their SMTP servers on an alternate port.

For example, my email provider, Everyone.net, lets me set up my email client to communicate on port 2525 (see Figure 9.40). To use this workaround, find out what your email provider's alternate SMTP port is; then go back into your email account in Windows Mail (this also works for other email clients) and click the Advanced tab.

Figure 9.40

Figure 9.40 Use an alternate SMTP port number if your ISP blocks third-party SMTP servers.

Under the Server Port Numbers area, change the outgoing mail (SMTP) port number to the alternate offered by your email provider. Don't forget to restart your email client and re-create any emails stuck in your outbox. You should now be able to send email freely.

Other Email-Blocking Culprits

If none of this worked, you might consider that your email program is not the problem. Third-party security applications, including antivirus scanners and antispyware scanners, can sometimes block email activity. Software firewalls can also cause grief.

If you use any of these applications, consider removing them (temporarily) to see whether they are the source of the problem. If you have set up two computers to check the email account, be sure they aren't checking at the same time. One will cause the other to error out (see Figure 9.41).

Figure 9.41

Figure 9.41 If two computers check the same email account at the same time, one of them will produce this error.

Also, a double firewall can be problematic. If you are using a third-party software firewall (perhaps inside a security suite from Norton or McAfee), be sure to turn off the built-in Windows Firewall. They might conflict.

Here's how:

  1. Log in as an administrator.
  2. Click the Window menu and type firewall; then click Windows Firewall when it appears in the menu.
  3. Click Change Settings.
  4. Click your way through the UAC challenge.
  5. In the firewall settings, select Off (Not Recommended) to turn off the Windows Firewall and click OK (see Figure 9.42).
    Figure 9.42

    Figure 9.42 If you use a third-party firewall, you don't need the Windows Firewall, so switch it off.

  6. A restart of your system and Windows Mail might be necessary.

If you have trouble with a stalled email in your outbox, be sure to re-create it in a new email and delete the original from the outbox.

Stuck emails often will stay stuck. So, it is better to remove the email from the outbox and make a new duplicate; then make email client changes and modifications to your security software (including firewalls), and then send the new email.

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