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I am following this document

http://kb.eclipseinc.com/kb/how-to-configure-iis-smtp-server-to-forward-emails-using-email-account/

and in places where it was talking about ports etc i used the information

Gmail SMTP server settings

  1. Gmail SMTP server name: smtp.gmail.com

  2. Gmail SMTP username: your Gmail address

  3. Gmail SMTP password: your password

  4. Gmail SMTP port: 465

I also enabled TLS

but mails sent just get stuck in queue

My Settings

SMTP_DeliverTab Outbound Connections Outbound Security Advanced Delivery Relay Restricions

1

Mails sent just get stuck in queue

You need to use port 587 with TLS.

  • Gmail SMTP port (TLS): 587
  • Gmail SMTP port (SSL): 465

Source What Are the Gmail SMTP Settings?


I'm getting an error message that my app is not secure

Someone just tried to sign in to your Google Account myaccount@gmail.com from an app that doesn't meet modern security standards.

You need to change a setting on your Gmail account.

  • Login to Gmail

  • Go to "My account"

  • Select "Sign-in & security"

  • Scroll to the bottom of the page

  • Set "Allow less secure apps" to "ON"

enter image description here

Try to send your emails again.


Allowing less secure apps to access your account

Google may block sign-in attempts from some apps or devices that do not use modern security standards. Since these apps and devices are easier to break into, blocking them helps keep your account safe.

Some examples of apps that do not support the latest security standards include:

  • The Mail app on your iPhone or iPad with iOS 6 or below
  • The Mail app on your Windows phone preceding the 8.1 release
  • Some Desktop mail clients like Microsoft Outlook and Mozilla Thunderbird

Change account access for less secure apps

To help keep Google Apps users' accounts secure, we may block less secure apps from accessing Google Apps accounts. As a Google Apps user, you will see a "Password incorrect" error when trying to sign in. If this is the case, you have two options:

  • Option 1: Upgrade to a more secure app that uses the most up to date security measures. All Google products, like Gmail, use the latest security measures.

  • Option 2: Change your settings to allow less secure apps to access your account. We don't recommend this option because it might make it easier for someone to break into your account. If you want to allow access anyway, follow these steps:

    1. Go to the "Less secure apps" section in My Account.
    2. Next to "Access for less secure apps," select Turn on. (Note to Google Apps users: This setting is hidden if your administrator has locked less secure app account access.)

Source Allowing less secure apps to access your account

  • You are correct i was using the wrong port after changing to 587 i got one partial success saying google prevented the sign in attempt coz app doens't meet modern standards but then after that nothing – SeanClt Jun 10 '16 at 21:50
  • @SeanClt What is the exact error message? – DavidPostill Jun 10 '16 at 21:59
  • no error message email just sits on the queue – SeanClt Jun 10 '16 at 22:09
  • @SeanClt So what is this "app doens't meet modern standards" then? – DavidPostill Jun 10 '16 at 22:10
  • Message in the email : Someone just tried to sign in to your Google Account myaccount@gmail.com from an app that doesn't meet modern security standards. – SeanClt Jun 10 '16 at 22:11

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