If you recognize the symptoms, this is probably the problem.
1. Two-factor Authentication
Symptoms: If you are getting an error message that indicates that you must create an application-specific password, you have Two-factor Authentication turned on. If you are not sure, or can’t remember if you have two-factor Authentication enabled, the first thing to do is check your email account's security settings.
Description: This is when you have two-factor authentication set up in the security settings of your mail provider (this can apply to any of the major mail providers).
To fix: You will need to go into your security settings and generate an app-specific password for SoftRAID, and then use that app specific password in the email notification settings.
2. OAuth problem (Gmail or Yahoo)
• You are unable to authenticate using your username and password and your provider is GMail/Yahoo, and a SoftRAID error dialog indicated that the problem is OAuth-related.
• In order to verify if this is your problem, you will have to:
- Log in to your email inbox
- Look for an email from your mail provider (GMail/Yahoo) that begins as in these examples:
Description: Google and Yahoo have adopted a new security protocol (OAuth 2.0) that by default, disrupts most desktop mail applications, SoftRAID included. Apple, however, has not implemented Oauth 2.0 for security reasons, so we are not going to support OAuth until Apple does. If SoftRAID’s email notifications fail for this reason, you will receive an email that indicates as much. This email includes instructions for resolving the problem.
The instructions to fix this issue are contained in the email Gmail sent you (along with scary warning text!)
In this email you will see the following sentence and link:
Click on this link to change your GMAIL settings to allow access for less secure apps.
Similarly, Yahoo includes instructions to fix this issue in the email they sent you:
Click on this link to change your YAHOO settings to allow access for less secure apps.
Less Secure Apps! What's that? Is it dangerous to change? (Hint: No)
Despite the alarming warnings, SoftRAID is not actually any "less secure" than any other mail client. As long as you are connecting with SSL or TLS, all communication with your mail server is encrypted, and safe from intrusion. The forced adoption of OAuth 2.0 is something of a political matter, disguised as a security issue. Even the original author of OAuth 2.0 now disavows the current implementation of OAuth 2.0, and its heavy-handed deployment by Google, Yahoo and Facebook. Check out the author’s blog post for more info, or one of the many news stories summarizing his blog post:
3. Problems using Gmail Accounts
Symptoms: You are a Gmail user and still unable to authenticate your email settings even after trying the other fixes listed above.
Description: Gmail may require you to complete a CAPTCHA challenge if their security system observes "odd" login attempts.
Some CAPTCHA triggers include:
For any of these reasons, Google may decide it needs you to complete a CAPTCHA in a browser before it can authenticate login. Google wants to be sure that the login is not a hacking attempt by some malicious computer program (bot).
If you want to read more, this page describes this issue pretty well:
• In a browser go to:
• Complete the CAPTCHA
• Retry the "Send Test Email" button in SoftRAID
4. SSL-related timeouts and Port 465
Symptoms: You are getting timeout-related failures and are using port 465
Description: Many mail providers instruct their users to use port 465 with SSL as the Connection Type. This usually indicates that the mail provider has port 465 set up for "implicit SSL". SoftRAID's email notification system only works with "explicit SSL" or TLS, both of which are usually configured on port 587. All of the mail providers that we have experience with offer one of the following:
• both implicit and explicit SSL
If you are interested in more information about implicit vs. explicit SSL, the
team at Fog Creek Software wrote a succinct post explaining this issue as it
relates to the email notification feature in product FogBugz: