How to set up SMTP for Microsoft Hotmail/Outlook

Modified on Fri, 15 Mar at 11:06 AM

Hotmail and Outlook accounts are hosted by Microsoft. Microsoft has introduced some additional security measures to protect your account that are beyond the typical SMTP connection process and they are set out in this article.
Getting Started: Email Configuration SMTP. Emails can be sent from Pet Sitter Plus in a few ways. 
  1. Through our internal email system (default).
  2. Through a combination of our internal email system and your business or personal email account (strongly recommended).
  3. Through your business or personal email account only. 

  • This step is not essential to use Pet Sitter Plus, but it can provide enhanced functions.
  • There is a separate process for Google accounts, please see Connect your Email using Google and Gmail
  • SMTP set-up can be a frustrating experience due to the technical nature. If you run into any difficulties, please reach out to our Support team who will be happy to assist you:

How Do I Set up SMTP for Microsoft Hotmail/Outlook?

Step 1: Email Options

Navigation: Admin > Settings > Email Settings >Email Options

  • BCC All Direct Emails To Company: Turn ON (Optional) to receive a copy of all emails sent via SMTP.
  • Click "Update."

Set Email Options to BCC All Direct Emails to Company in Dog Walking Software

Step 2: Email Options

Navigation: Connect > Email Settings > Connect Your Email

  • Send Email From Your Own Account: Turn ON to configure SMTP.
  • Email Configuration Type: Select SMTP.
  • Only Use For Direct Emails: Turn ON (Highly Recommended). You should continue to send Invoices and other emails through the internal server.

Settings for configuring hotmail email in dog walking software

Step 3: Email Configurations

Navigation: Connect > Email Settings > Email Configuration

Complete the SMTP configuration with your email account details (as in the example below).
  • Sender Email: Your Microsoft Hotmail/Outlook email address
  • Host: eg. "" or ""
  • Username: Your Microsoft Hotmail/Outlook email address
  • Password: The password for your Microsoft Hotmail/Outlook email account (NOT your Pet Sitter Plus login password)
  • Security: Select STARTTLS
  • Port: Enter 587
  • Click "Test & Update."

Note: Your first attempt at connecting with "Test & Update" will likely fail. This is normal due to the security settings you need to alter on your Microsoft Hotmail/Outlook Account.

connection failed error message in dog walker software

Troubleshooting Microsoft Hotmail/Outlook

Step 1: Turn on Two-Step Verification

  • In order for Pet Sitter Plus to "talk" to your Microsoft Hotmail/Outlook account via SMTP you need to set two-step verification to “Turn on”.
  • See below for instructions on how to do this. To find out more information about 2-step verification, please make sure you are logged into your Microsoft account and click the link below
  • From your Microsoft account, click the option on the top menu for "Security".
  • Next, click the option called "Advanced security options".

Set up security in Microsoft to use with your dog day care software

  • On the "Advanced Security Settings" screen, scroll down to "Additional security" until you see "Two-step verification".
  • Click "Turn on".

Set up security in Microsoft to use with your dog walking software

You will be taken through several steps to verify your devices. Look out for an email from Microsoft to take you through these.

Step 2: Create an app password to use with Pet Sitter Plus

  • Under the "Additional security options", you will see "App passwords".
  • Click "Create a new app password".

Set up security in Microsoft to use with your dog walker software

  • Microsoft will create a new password for you to use in Pet Sitter Plus.
  • Drag across the password with your mouse and right+click to "copy" the password.

Set up security in Microsoft to use with your pet sitting software

Step 3: Add Microsoft generated app password to your Email Configuration

  • "Paste" the new password from Microsoft into the "Password" field in the Custom SMTP Configuration.

Retrying to Connect
  • Having completed steps 2 to 3 above, click “Test & Update” again and the connection attempt should now succeed.

An email is sent to the address you have stored in the “Email Address” field in Admin > Settings > Company Information.

Connection succeeded message in cat sitting software

Email Confirmation
  • You should receive an email with a "Success" message in the subject line to confirm that SMTP is now working.

Success email received after connecting hotmail or outlook email in pet sitting software

Tip: Once you have successfully completed the connection, a new option to email your clients in bulk from the Client Search is available, like this: 

Bulk emailing your clients in your pet sitter software

Note: Some clients have reported varying success with connecting Microsoft accounts via SMTP as the way everyone logs in is different depending on what type of MS account you have. If the above method is not successful for you, please out to our Support team who will be happy to assist you:

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