Send Emails via Microsoft Office 365

Using HirePOS to send emails via your Office 365 account can be very beneficial, it will reduce the chances of emails going into Spam drastically, and sent emails will appear directly in Outlooks "Sent" box.

Setting up HirePOS to use Office365

  1. Navigate to Setup > Preferences > Email Templates & Settings
  2. Press the Edit cog link to the right of the From Address
  3. Select either Main Business Email or Other Business Email Address from the first set of options
    1. In the case of Other Business Email Address be sure to set an address that has "send as" permissions enabled for the Office 365 account you are planning to add. (by default, the only address you are able to send as on an office 365 account is the actual address of the account)
    Important: You will only be able to send from an address that has "send as" permissions in the Office 365 account you are adding.
  4. Below the email address field on this screen, select the option Your SMTP Server
  5. Press the SMTP Settings button

The SMTP Settings Page

  1. Enter your SMTP Username. In the case of an Office 365 account, this will typically be your Office 365 email address.
  2. Enter your SMTP Password. This is the same password you would use to log into outlook online or your office 365 portal with the above username.
  3. Enter the SMTP Server. This is typically for Office 365 accounts.
  4. Enter the SMTP Port. This is typically 587 for Office 365
  5. Select Use SSL
  6. If you have a secondary account you wish to add, press Add Another SMTP Account, and repeat the above
  7. Press Save Changes

Testing if it worked

  1. After saving, navigate to CRM > Send Email (or attempt to email a booking or invoice to yourself)
  2. Ensure the From: address is set as the email address you have just set up
  3. Enter your own email address or the address of another inbox you have access to in the To: field
  4. Add a subject like test or similar
  5. Add some body test like test or similar
  6. Press Send
  7. Give it a couple of minutes, and check the sender information on the email you should have received in your inbox.

It didn't work...

I got an error
The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.7.57 SMTP; Client was not authenticated to send anonymous mail during MAIL FROM ...
Often the result of attempting to send with a From address other than the one used for the SMTP connection. Could also be the result of a bad username and password.
An error mentioning "Timeout"
Usually the result of a bad username and password, or intermittent network issues.
An error mentioning "SSL" "TLS" or "STARTTLS"
It is possible you have entered an incorrect Port Number or SMTP server, or have not selected the SSL checkbox.
Other common causes of the above errors, or other errors
It is possible that SMTP connections of this sort have been disallowed my your IT department or provider. This is common with office 365 subscriptions purchased through a provider external to microsoft (such as Telstra or GoDaddy). It is also common for this to be disallowed by I.T departments in businesses for security reasons. It you are able to raise this with your I.T people, they might find the following microsoft document helpful:​
It never arrived
  • Give it a couple more minutes... sometimes emails are slow.
  • Check the junk / spam folder in the planned recipients email account
  • Ensure that all addresses have been entered properly
  • Contact your IT department to see if it has been caught up in their filters before it got delivered

Limitations of using your own SMTP server

The main limitation of this method, is HirePOS can only use two different emails to send out, Unless your email account has permissions to "Send as" a different account in the same domain. More info on this is available on this Microsoft article:


Connecting your own SMTP server is far from the only option available for setting up spam free email with your branding on them. Consider authenticating your domain with HirePOS (giving HirePOS proper permission to pretend to be you when sending email).

Many people find that custom branding is less important than ensuring the mail absolutely arrives at its destination. If this sounds like you, consider using the in-built, ready to go, option.

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