Connecting GoPhish with Office365
Operational challenges of setting of Office365 SMTP with GoPhish
$UserCredential = Get-Credential
$Session = New-PSSession -ConfigurationName Microsoft.Exchange -ConnectionUri https://outlook.office365.com/powershell-liveid/ -Credential $UserCredential -Authentication Basic -AllowRedirection
Import-PSSession $Session -DisableNameChecking
Take a look if it is True: Get-TransportConfig (if there is True set to false)
Set-TransportConfig -SmtpClientAuthenticationDisabled $false
Take a look again if it works: Get-TransportConfig
Use the Administrator account (Generally the one which was used to create office365 account) to enable SMTP. I have seen that newer accounts already have this setting enabled by default. If your account is not working try this out.
If above doesn't work for you. Try the following code. Credits Jonathan Cheung
Add Connector to Exchange Admin
You will need to provide you GoPhish External IP to add this connector. The connector properties are From: Organization Mail Server , To: Office365, and then you need to add your External GoPhish IP
Click on Connection -> Protection Filter > Connection Filtering
Here you need to Whitelist your external Exchange IP
Whitelist your External GoPhish IP
You should be good to go now. Enter your creds inside Gophish and send a Test Email.