SSL certificate warning on devices when connecting to a mail server

Email SSL certificate warning on Apple (and other) devices when connecting to a mail server

Email software and apps running on an Apple device (i.e. macOS or iOS) will require you to make an exception if the SSL certificate provided by the server doesn’t match the hostname you’re connecting through. If this SSL certificate is changed or renewed, which will happen at least once a year, another exception would need to be made.

A similar issue can also appear using various email clients on other systems such as Windows, Linux and Android.

By default, the mail server we would advise you to use would utilize your own domain name (e.g. mail.yourdomain.com). This will allow you to connect through a mail client, but if you attempt to connect with SSL enabled this will show a warning, something like: Certificate Mismatch. The recommended method of enabling secure connections would be to connect using the mail server’s actual hostname (e.g. mail123.extendcp.co.uk).

Most email software and apps will allow you to either ignore the warning or provide an exception. Apple devices should let you do this the first time you connect, but when our SSL (*.extendcp.co.uk) renews, Apple devices will show another Certificate Mismatch error similar to when you set the email account up, but won’t allow you to ignore the warning.

To set this up correctly you should change the incoming (IMAP/POP3) and outgoing (SMTP) servers to use the actual hostname of the server. If you don’t have the *.extendcp.co.uk type hostname please contact support with your domain name so that we can supply you with your email hostname.

Alternatively, you can just turn off ‘Use SSL’ in the settings by going to:

1. Settings
2. Passwords & Accounts
3. [Your Account]
4. IMAP
5. SMTP
6. Primary Server
7. Turn Off ‘Use SSL’
8. Done
9. Account
10. Advanced Settings
11. Turn Off ‘Use SSL’
12. Account
13. Done

This does however mean that your connection to the server will not be secured.

Or you can try to add another certificate exception manually via Keychain, but this isn’t something Support would be able to help with.

A final option would be to remove the email account from the device and then add it back again so that a new exception (Trust) can be created. We only recommend this option if you are using IMAP and all your existing messages are kept on the mail server. If using POP3 you would need to ensure that your email messages are fully backed up before deleting.

Also, if you ever find that this hinders you from accessing your email, you can also access your email using Webmail at https://outitgoes.com (or webmail.yourdomain.com).

How do I set up a mailbox using IMAP on my device?

Our standard and premium mailboxes can be loaded onto your device or through your mail client either with a POP3 connection or an IMAP connection.

By using an IMAP connection, you can have multiple clients simultaneously connected to the same mailbox.  For example, you can have email on your phone, your tablet, and your computer, and when you delete a message from your phone, it will also be deleted on your other devices.

The way your device or mail client is designed may be different than how other programs or devices work, with different names for the same steps.

Your device or program should have detailed information on how to add and set up mailboxes onto the system, but there are general pieces of information you need to complete the process.

When selecting the account type, select IMAP.

Your Username is your full email address.

Your Password is your mailbox password.

You can change an existing password from the WebMail site at https://outitgoes.com. If you have forgotten your mailbox password you can change this from your Control Panel at https://extendcp.co.uk. The password change can be found under ‘Mail Boxes’.

Your Incoming Mail Server (IMAP) and Outgoing Mail Server (SMTP) are both mail.yourdomain.com.

So, for example, if your name is John and your domain name is mydomain.com:

Username: john@mydomain.com
Password: a-STRONG-Password-5GZ8
Incoming Mail Server: mail.mydomain.com
Outgoing Mail Server: mail.mydomain.com

In the Advanced Features for Outgoing Mail Server, there may be some additional settings that need changing. Please make certain that:

  • You are using the default ports (25, 465, 587)
  • You are or are not not using Secure Sockets Layer (SSL)
  • You are using Password for Authentication

Your mail client may tell you that the mail server security certificate doesn’t match and will ask you to either trust or reject the certificate. This happens because our mail server certificate name isn’t the same as your domain name, but it’s safe to ‘Trust’ the certificate when asked.

What are the limits on my email accounts?

To protect our servers, we have placed limits on some email features, including the number of emails you can send, the size of your mailbox, and the file size of attachments.

Sending Emails

For emails you are sending, the limits are:

  • WebMail: 50 emails per day
  • Desktop client or device: 500 emails per hour, with 100 recipients per email
  • Website script that sends email: 1,000 emails every 12 hours
  • Mailing list: As many emails as you like, with 2,500 subscribers per list

We have a Zero Tolerance policy on users sending unsolicited email.  If our systems are deliberately used to send unsolicited email, we will suspend the user’s account.

Email Attachments

The limits on attachment sizes are:

  • Using WebMail: 2MB in total
  • Using a mail client or a device: 30MB in total

When you attach a file to an email, it increases in size, and even though the file may be smaller than the limit when you check its properties as a separate file, it may be over the limit when attached to an email. We also have no control over the limits set by other companies, who may have set their limits much lower – some even down to 2MB.

If you attempt to send an email attachment over your limit or your recipient’s limit, the email will be bounced back to you.

If someone sends you an email with attachments larger than 30MB, that email will be bounced back. The sender will receive a message informing them that the message size exceeds the size limit for your server.  You must then contact the sender to work out another way of sending attachments.

One way of sending large files to your recipient is if you both use Microsoft Outlook or Microsoft Outlook Express.  Certain versions of this software includes a ‘Break apart messages’ feature, where you can break an attachment up into sequential emails and they are recombined on the recipient’s computer.

Mailbox Size

The size of your mailbox will depend on which email package you have:

  • Standard Mailbox: 1GB capacity
  • Premium Mailbox: Initial 2GB capacity, but can be upgraded to 10GB in 2GB increments
  • Exchange Mailbox: 30GB capacity

If you use our WebMail or IMAP, this capacity includes all attachments and any emails you have in the ‘Trash’ but have not deleted.

If you are close to your 1GB mailbox limit, emails sent to you that would cause you to exceed your limit will not be delivered to your mailbox.  If you receive smaller emails, but not the larger ones, this could be what is causing that problem.

Please note: As part of our regular server housekeeping, any Standard Mailboxes that have not been checked for 100 days may be automatically deleted.

If your Standard Mailbox is too small, you can increase the capacity by upgrading to a Premium Mailbox. Your mail will be automatically transferred over, with no loss of data.

How can I connect to my mailbox with a secure connection?

We do support SSL encryption for all mail connection protocols.

If you are using our WebMail at http://webmail.yourdomain.com or http://www.outitgoes.com, you can access a secure version at https://www.outitgoes.com.

If you are connecting to your mailbox through a desktop-based email client, the ports are:

POP3: 995
IMAP: 993
SMTP: 465

Be certain to select the option in your mail client to use secure password authentication when using a secure connection.

You may receive a warning when making a secure connection to your mailbox. This is a common warning, and you can accept the certificate permanently despite the warning.

How do I set up an Exchange mailbox in Outlook for Mac?

Outlook has full support for automated setup, so configuring your mailbox is very simple:

1) Open Outlook. If this is your first time running the software, a “Welcome to Outlook” screen will be displayed. Select “Add Account” and go to step 4, otherwise go to step 2.
2) Select “Outlook” from the menubar, and select the “Preferences” option.
3) Select “Accounts”.
4) Select “Exchange Account”.
5) Enter the following into the visible fields:

E-mail address: Your Exchange mailbox address.
Method: User Name and Password.
User Name: Your Exchange mailbox address.
Password: Your mailbox password.
Leave “Configure automatically” selected.

6) Select ‘Add Account’.
7) Outlook will then attempt to automatically detect your mailbox settings. During detection, a message should pop up informing you that “Outlook was redirected to the server ‘Exchange.outitgoes.com to get new settings” – select ‘Always use my response for this server’ and select “Allow”.

If automated setup doesn’t work, complete steps 1-5 as above, but unselect “configure automatically”.

6) In the “Server” field, enter https://exchange.outitgoes.com/EWS/Exchange.asmx
7) Select “Add Account”.
8) Select “Advanced”
9) In the “Server” Tab, set the following:

Microsoft Exchange
Server: https://exchange.outitgoes.com/EWS/Exchange.asmx : 443
Use SSL to connect – selected

Directory Service
Server: EXCHDC2.exchange-outitgoes.com : 3268
Log in with my Exchange account credentials – selected

How do I set up an Exchange mailbox in Outlook?

There are two ways to set up an Exchange account, automatically and manually. We recommend trying the automated method first:

1) Ensure that Outlook is closed, or you will not be able to add an account.
2) From the Start Menu go to your Control Panel.
3) Select ‘Mail’.
4) Select ‘E-mail Accounts’.
5) Under the ‘E-mail’ tab select ‘New’.
6) Select’ E-mail Account’ then ‘Next’.
7) Here you should enter your name, email address, and mailbox password.

If this is not successful, you can take the following steps to set up the mailbox manually:

1) Again, you’ll need to set this up via the ‘Mail’ section of your control Panel.
2) Select ‘Add New Account’.
3) Select ‘Manually Configure Server Settings’.
4) Select’ Microsoft Exchange’.
5) Under ‘Server’ enter ‘outlook.exchange-outitgoes.com’ and under ‘User Name’ ‘name@domain.com’
6) Under ‘More Settings’ go to the ‘Connection’ tab and tick ‘Connect to Microsoft Exchange using HTTP’.
7) Select ‘Exchange Proxy Settings’.
8) In the ‘URL’ field enter ‘exchange.outitgoes.com’ and under ‘Proxy authentication settings’ select ‘NTLM Authentication’.

How do I set-up a mailbox in Thunderbird Mail?

To add an email account (or mailbox) in Thunderbird Mail:

1) Go to the ‘Tools’ menu, and click ‘Account Settings’.
2) Click ‘Add Account’ – make sure ‘Email account’ is selected and select ‘Next’.
3) Fill in your name and Email address.
4) Select POP or IMAP, your incoming mailserver will be in the format mail.example.com (replace example.com with your domain name).
5) Your incoming User Name is your email Address.
6) The name of the account is entirely up to you – click next until the account has been created.
7) Now We need to set up SMTP – click on ‘Outgoing Server (SMTP)’.
8) The Server Name is the same as your incoming mailserver.
9) The username will also remain the same (your email address).

Please see our support page for a download link for Thunderbird Mail.

How do I filter out spam or junk email?

To do this, log into your Web Hosting Plus Control Panel and select Email Configuration. In the following list select ‘Junk Mail Filters’ where available in your account type.

Junk mail filters use special technology to filter out junk mail before you receive it. This feature also allows you set an address to send the junk mail to so that you can check this address to ensure that only junk mail is being caught.

Please keep in mind that spam filtering is not always perfect – there can be false-positives and false-negatives, so do keep an eye on your spam mailbox for mail that’s been incorrectly filtered, and do watch out for phishing emails that slip through the filter – if it doesn’t look genuine, contact the supposed sender directly.

Why can’t I send email?

There is a possibility that your ISP (Internet Service Provider) is blocking port 25. Providers like AOL block this to prevent outside users from relaying bulk email off their servers. You should contact your provider to see if port 25 is blocked.

Otherwise you have incorrectly entered details in your email software for the outgoing server (SMTP) for example make sure you are authenticating the outgoing mail server as described in other support articles, or software on your machine like anti-virus, firewall, Norton, Symantec, etc., is conflicting.

If port 25 is blocked, you could try using port 587 instead.

What is the difference between POP3 and IMAP4 mail?

You may have noticed with your email software, and with our webmail facility, that you are given the option of accessing your email through either POP3 or IMAP4.

These are two different protocols. With your email software, POP3 is downloaded directly from the mail server onto your computer. Your computer will store a “local copy” of the email, and usually delete it from the server. You can create local folders on your computer to organise the email, but you won’t see these or your email if you’re logged in using webmail.

Additionally, if you create folders to organise your email in webmail, you won’t be able to access these with your email software. Email will therefore only contribute towards the mailbox limits while it is left un-downloaded in the inbox.

IMAP4, in contrast, is left on the server (where it will continue contributing towards your mailbox limit). If you create folders/organise email with your email software, you will see this update when you log in to webmail (and vice-versa). Similarly, when you mark a message as “read” in webmail, it will appear “read” in your email software.

If you’re accessing your email on several different computers, IMAP can be useful. However, if you expect to receive high volumes of email, or want to be able to access your email offline, POP is the better option as it will be downloaded and stored on your computer.