Does gmail have to be logged in to send messages via Sinatra/Pony?

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I'm currently using Pony with my Sinatra app and it's set up to send an email via gmail whenever a user registers. It works perfectly fine, however when a friend of mine tried to register he encountered an Internal Server Error.

He was successfully added into the database, but he didn't receive any emails. I used to receive this Internal Server Error whenever Pony didn't fire correctly on my end, so I'm wondering if my gmail (the one linked in Pony to send the emails) needs to be logged in on my end 24/7 for my app to work as intended?

Thanks in advance.

Edit: Seems like adding an app password solved the issue.

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If you run into errors like Net::SMTPAuthenticationError while using gmail for sending out emails (common for Google Apps accounts), visit your gmail settings and enable less secure apps to get the application working.