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FAQ - Email Configuration Problems

Email configuration failures generally happen for one of the following reasons:

1) Two-factor authentication
2) Oauth
3) CAPTCHA
4) SSL-related timeouts and Port 465

Below are methods for diagnosing which particular problem you may be having.

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)

Symptoms:
• 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:

GMAIL:
Subject Line: Review blocked sign-in attempt
Body:
Hi ____,
Google just blocked someone from signing into your Google Account
____@gmail.com from an app that may put your account at risk…

YAHOO:
Subject Line: Sign in attempt prevented
Body:
Hi _____,
Your account is currently not enabled to sign in from apps, that do not meet
modern security standards (ex. Older versions of mail and calendar apps such as
Outlook). As a result, we prevented a sign in to your Yahoo account…

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.

To Fix:
GMAIL
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:

You can continue to use this app by allowing access to less secure apps
https://www.google.com/settings/u/1/security/lesssecureapps

Click on this link to change your GMAIL settings to allow access for less secure apps.

YAHOO
Similarly, Yahoo includes instructions to fix this issue in the email they sent you:

Go to https://login.yahoo.com/account/security#other-apps and turn on the setting labelled: "Allow apps that use less secure sign in."

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:
https://www.cnet.com/news/oauth-2-0-leader-resigns-says-standard-is-bad/
https://hueniverse.com/2012/07/26/oauth-2-0-and-the-road-to-hell/

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.

What's a CAPTCHA?

Some CAPTCHA triggers include:

  • A user tries and fails to log in too many times (how many is up to Google)
  • A user signs in from a new geographic location or internet provider for the first time (for example, a coffee shop)
  • A user has taken steps to overcome the OAuth problem by allowing less secure apps

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:
https://gmailhelp.com/unlocking-googles-gmail-captcha/

To fix:
• In a browser go to:
https://accounts.google.com/DisplayUnlockCaptcha
• 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
• TLS

To fix:

  • try changing to port 587.
  • if you are still having trouble, check with your mail provider's outgoing SMTP settings to see what other outgoing ports they offer.
  • If you are still having problems, contact SoftRAID Support, and we will work with you to fix the issue.

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: http://help.fogcreek.com/9002/using-an-smtp-server-with-ssl