How To Fix Common Email Problems [MacRx]


Email Apps

As an IT consultant you get accustomed to certain problems and complaints from users.  “My computer is running slow” is a universal favorite.  “You said this would only take a few minutes” is another perennial frontrunner.

But one stands out as arguably the most common end user headache: “My Email Isn’t Working.”

Sigh… Welcome to the club.  Email headaches are endless.  Fortunately, many issues are common problems that can be fixed relatively easily.

There are two primary ways to send and receive email:  using an Email Application and using Webmail.  Many problems are common to both types of access, some are specific to one or the other.  It helps to have both methods for troubleshooting and workarounds – try using webmail when your email software isn’t working, or vice versa.  This can definitely help in a pinch.

Common Problems Receiving Email

Wrong Username or Password
Some email providers require that your entire email address to be entered as the username when signing in or setting up your email software:

Other providers require only the portion to the left of the @ sign:  myname

Try both methods when this problem occurs.  Also check for typos, particularly in web browsers that auto-enter saved data into forms.

Password errors are often presented in conjunction with username errors: Wrong Username or Password.  That makes it hard to know which item is incorrect.  However one common password problem is case sensitivity – does your provider pay attention to upper- and lowercase letters?  Many do, so that may be an issue.

Most people also have multiple passwords – some current, some in varying degrees of obsolescence, and some forced upon us whether we liked it or not.  Try the usual favorites when one doesn’t work.  Sometimes a previous password change request may not have completed successfully.

No Response or Error Contacting Mailserver
Many times email is working perfectly one minute then stops for no reason.  Often these issues have nothing to do with your email account or program, but it can be tough to tell what’s going on.

First thing to check: do you still have internet access?  Open a web browser and try visiting any website (Google is a good quick check).  If you can’t reach anything the problem is not just with email.  This sounds obvious, but I give this simple troubleshooting suggestion to people several times a month over the phone.

Assuming you have internet access, next determine if the problem is with your system or the email server.  If two or more people can’t get email it’s probably a server or network problem.  Try using webmail to access your account.  If that works, quitting and relaunching your email program might help.  If webmail doesn’t work, the problem is likely with the email server.

Wrong Port or Security Settings
This problem is more advanced and typically affects email applications accessing POP and IMAP accounts. Email accounts get configured using specific server names, port numbers and security settings (SSL data encryption On or Off).  Default values are often set during account configuration, and these may need to be changed.

For POP accounts, the default settings are port 110/SSL off.
If your provider requires a secure connection, use port 995/SSL on.

For IMAP accounts the default settings are port 143/SSL off.
If your provider requires a secure connection, use port 993/SSL on.

Message in a Bottle
Image: kraftwerk via flickr (CC licensed)

Common Problems Sending Email

Problems sending email are more frequent than problems receiving email.  Security settings and port restrictions are an attempt to stem the tide of spam and prevent unauthorized use of mailservers.  Alas these efforts often seem to thwart legitimate users more than spammers.

Wrong Username/Password
Username and Password issues can affect both sending and receiving email.  As with receiving mail, check both styles of username – and myname – and verify correct case on passwords.

Incorrect Authentication
is the way in which an email application provides a user’s account information to the mailserver, rather than just what it provides; it’s a set of protocols for verifying identity.  There are different settings you can choose for Authentication – Password, MD5 Challenge-Response, Kerberos, etc..  Choices and wording vary by program.  If you get an Authentication error when sending mail check this setting, it may not be the password which is incorrect.

Some cable and T1 providers use None (No Authentication) when you are sending email while on their networks.  Try this option when nothing else works.

Wrong Port and Security Settings
Outgoing mailservers (called SMTP servers) also require specific port and SSL settings:

SMTP default settings are port 25/SSL off.
Secure connections use port 587/SSL on, or (sometimes) port 465/SSL on.

Try these different combinations in your account setup preferences when you can’t send email.

ISPs can change security settings without prior (or adequate) warning.  In the Boston area over the past year changes have been occurring in individual towns by provider with little rhyme or reason.  On different random weekdays I’ve gotten batches of calls from clients suddenly unable to send or receive email.  I have them check the port and SSL settings, then ask “who’s your provider?”

10 minutes later another caller, same town.  Soon a third.  “You using Comcast?”

“Yes, how’d you know?”

Thus goes an entire morning.  Really cuts into my Dunkin’ time…

Too Many Attachments or Message Too Large
Simple rules here: don’t send to too many items in one email, and keep attachments as small as possible.  Specific limits as to how much data you can send with an email vary by provider, but generally the more stuff you add the more potential for problems to occur.

Workarounds for attachment problems include splitting up your batch of photos/movies/documents  into several emails, each with fewer individual attachments; sending the attachments as a single .zip archive; or posting to an intermediate server (FTP, corporate fileserver, etc.)

Use Webmail as a Workaround
Webmail is a good workaround when you’re stuck or traveling.  The webmail interface to a server doesn’t send or receive messages across the internet as POP/IMAP/SMTP exchanges, but rather as web traffic.  This allows email access when on networks which block dedicated email ports.

For example, Panera Bread provides free WiFi in their restaurants but blocks outgoing email ports (at least in the locations I’ve visited).  I can receive but not send messages using Apple Mail.  As a workaround I login to my webmail account, which isn’t blocked, then send and receive messages from there.  Problem solved.

  • Chapino1

    I do not know what I did, I currently cannot view any of the 90 unread mail items in one of my mailboxes, how do I get them to reappear?