1 &#; Check your internet connection

Strangely enough this is the most common cause of Apple Mail asking repeatedly for a password.

If your internet connection drops out, even just temporarily, Apple Mail will often ask for a password. This is because it’s unable to make a successful connection to the email service provider. Apple Mail seems to always assume this is a password problem, instead of checking first whether the internet connection is actually working.

The easiest way for most users to check their internet connection is to try loading up any website. A particularly good test is to perform a Google search for something very random. That way you know that the browser isn’t loading up a previously-saved page and must therefore have internet access.

If you definitely have internet access, restart your Mac from the Apple menu (top left of screen) > Restart. This sounds like overkill, but it guarantees Apple Mail has been fully quit and reopened. It’s easy for inexperienced users to simply close the Mail window and not fully quit the app. After restarting, check whether the email password prompt has now disappeared.

2 &#; Check whether your email password has actually changed

This is slightly harder to troubleshoot because everybody will use one of several hundred different common email providers.

The basic trick is to log into the email provider’s webmail service to verify the password you’re trying is definitely % correct. Obviously, a successful login to the email provider’s system confirms that the password you have on file is accurate.

“Webmail” is simply a website, provided by your email service provider. This allows you to browse your email directly without having to set up an app (such as Apple Mail or Outlook) on your computer.

Finding Your Webmail Login

Obviously, it helps to know your email provider. However, you’ll usually be in one of these categories:

1. If it’s a business email address, speak to your business IT person or IT support provider. They will usually be able to tell you the website address (“URL”) for webmail. They may also be able to confirm your password directly.
2. If it’s a personal email address, usually your email provider will be one of a handful of major platform providers (see table below “Major UK Email Platforms”).
3. If you have a custom domain name and your own website, you can ask your website developer for the webmail address.
4. If you have a custom domain name but you do NOT have a website, try… https://mail.conwaytransport.com.au …where conwaytransport.com.au is replaced by your own custom domain name (the bit after the @ symbol in your email address).
5. If you have a custom domain name but don’t have a website developer, and (d) doesn’t work, you should check with your domain registrar. This is the company with whom you registered your domain name. If you’re not sure who the domain registrar is, enter your domain name (the bit after the @ symbol) into this website: conwaytransport.com.au

Major UK Email Platforms

Once you have identified your webmail login address, try signing in with your email address and the password you have on file. If it works, we can be sure you have the right password for the email account, so there must be some other problem aside from a wrong password.

Of course, if you have the wrong password on file, there is the problem. You may need to follow the Reset Password procedure for your email provider, which is usually available at the webmail login page. Or, contact the provider’s support service directly. They can help you reset the password to a known value.

Once the password is set to a known value and you can log into webmail. Follow the password error prompts on your Mac or iPhone to update the password to the correct value in Apple Mail.

You might find that you need to restart your Mac from the Apple menu (top left of screen) > Restart before the new password is accepted.

3 &#; Your password needs to be changed or updated

Sometimes, your email provider will enforce a password change for security reasons. When this happens, you are usually blocked from sending and receiving email until this has been actioned.

Apple Mail is unable to notify you of the exact problem because password policies are unique to the email service provider. There is no globally recognised system to notify you of a specific password issue. Simply, you will just find that your password is refused as if it’s incorrect, resulting in a repeat password prompt in Apple Mail until you fix it.

Generally speaking the fix is to log into your webmail service &#; see section 2 above.  This will usually guide you through whatever needs doing with your password. Often, at the point of logging in, you will be prompted right there to update or change your password to meet the new policy.

Having done this, you can respond to the password prompt in Apple Mail and enter the new password when prompted.

As ever, you might find that you need to restart your Mac from the Apple menu (top left of screen) > Restart before the new password is accepted.

4 &#; You need an app-specific password

This is a new requirement of many of the larger email service providers.

App-specific passwords are a security measure which ensure your master email account password is not stored on your computer. It also will not repeatedly transmit back and forth to the email provider in order to retrieve email.

Instead, you have two passwords:

1. The first password is the ‘master’ account password. It usually allows you to sign into webmail &#; see (2) above &#; and manage your account, billing and so on.
2. You then have a second (or more) app-specific passwords which are different from the master account password. Often they are generated for you and will be highly random, making them unlikely to have been used elsewhere. You will be required to input an app-specific password in your Apple Mail or iPhone Mail settings, at the password prompt, not the master account password. Sometimes, if you use the master account password by mistake, you’ll be sent an email to notify you of the error. This of course is a catch situation because you probably won’t be able to receive new emails at the time, so you won’t see the error.

App-specific passwords have several security advantages. If you’re using an older device with older software, for example macOS Sierra or an older iOS version on your iPhone, this will be inherently less secure than the latest macOS or iOS / iPadOS software. By forcing those devices to use their own dedicated and highly random password, you’re limiting the damage if that password ever became compromised due to a security flaw.

Similarly, the pre-allocated and random nature of the app-specific password means that you’re forced to use the password you’re given. You can’t be tempted to re-use another, simpler password that you can remember. This is by far the most common cause of email hacking, identity and financial fraud.

5 &#; Your email system uses “OAuth”, “Modern Authentication”, “Two-Factor Authentication” or “Multi-Factor Authentication”

Many modern email systems recommend or require stricter, modern methods of logging in. The most common is two-factor authentication (2FA for short).  We’ll use as the example here to highlight the general nature of this specific problem.

If your email system requires 2FA, you must provide not only your email address and password to send and receive mail via your email program, but also a special time-limited 6-digit code. This is usually sent to you by text message or calculated using a code generator app on your phone.

This has obvious security benefits &#; a hacker cannot compromise your email account. Even if they have managed to obtain your password, as they won’t be able to generate a valid one-time passcode. This is because they are unlikely to also have access to your phone.

The problem is that most email systems like Apple Mail and Outlook only have the facility to enter a username and password in their settings. A one-time code has to be entered and submitted at exactly the right time for it to work effectively and it changes every 30 seconds.

To get around this, Apple Mail on macOS (High Sierra) and above supports what is broadly termed “modern authentication”. You set up your email account by providing an email address only, then you see a popup window (which is actually the email provider’s website) where you enter the password and the one-time code.

If successful, your Mac or device will be issued with a special token which totally replaces the username and password. So next time your email app connects to the email provider’s system to retrieve new messages, instead of transmitting a username and password across the internet, it simply presents the token. This is worthless to a hacker and therefore very much more secure.

You may however encounter a problem, manifesting as a repeat password popup warning, if you have enabled 2FA on your email account but you are running system software older than macOS High Sierra (or iOS 11). These don’t understand how to handle the token system which modern authentication uses.

Software update

In either case, you will need to update your Mac’s system software via the App Store, or on iPhone or iPad, use the Settings app > Software Update.

Some hardware will simply not support the necessary system software version and you won’t be able to update any higher. If this is the case, you will probably need to find out how to generate and use an app-specific password with your email provider (see 4) as a workaround.

6 &#; Your email provider isn’t very reliable

Many times we find new clients using a low-quality and unreliable email service.

Often the email service is tagged on to back of their website hosting. Or the email address has been supplied by their internet provider such as BT, Virgin, Plusnet, TalkTalk and so on.

These email providers are rarely reliable, as quite simply, the service is usually free. Supporting and maintaining a reliable email service is time-consuming. It requires specialist knowledge and infrastructure, which obviously comes at a price.

For usually no more than £5 a month you can choose to use a dedicated email provider. Their service will be far more reliable than a free system. You can usually choose to automatically forward emails from your old address, so nothing is lost. Or in the case of custom domain names, you can migrate your entire service and email history to a new provider and retain the exact same email address.

If you are getting constant password popups for Apple Mail or any other email application, and you have exhausted the above troubleshooting steps, maybe your email provider is just having a bad day and rejecting your connections.

One again, as ever, be sure to restart your Mac from the Apple menu (top left of screen) > Restart. This fixes a lot of problems that aren’t anything to do with the email provider. But if you keep on getting issues with your email, be sure to get in touch and we’ll help solve email reliability problems once and for all.