We have a server in Michigan and one in Arizona that might be trying to log in to your email account. Google's security will sometimes decide it looks suspicious.
A couple things you can try when this happens. It may take more than one of these steps to fix it:
1. Setup the 2 factor authentication and app specific password if you didn't already. Use if for both the SMTP and IMAP settings in InflatableOffice (see below).
2. Go here and set it to ON: https://www.google.com/settings/security/lesssecureapps
3. Go here and follow the instructions: https://g.co/allowaccess
(the above steps were taken from this page: https://support.google.com/accounts/answer/6009563)
We are looking into a better authentication method as a long term fix for this.
2 factor authentication
Choose Mail on my Other (Custom name) and type IO and hit generate. Copy the password into InflatableOffice SMTP.