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Can Gmail / Google Apps / G-Suite be used for SMTP relay?

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SMTP Delivery in PRTG works in Automatic SMTP Delivery Mechanism, but I wanted to know why it doesn't work if I enter the SMTP server relay info myself (same account info).

If I select via SMTP Relay Server option, the logs show:

Error sending "Email": Connection failed ("smtp.gmail.com")

Settings Used:

Sender E-Mail: <[email protected]>
Sender Name: <User Name>
HELO Ident: <ServerHostName>
SMTP Relay Server: smtp.gmail.com
SMTP Relay SMTP Port: 587
SMTP Relay Authentication: SASL authentication is required (also tried std smtp)
SMTP Relay Username:  <[email protected]>
SMTP Relay Password: <User Password>
Use TLS: <yes>

Same SMTP / account information also works in the sendemail.exe utility you can find online. Is there something I'm missing as to why it won't work on PRTG?

gmail google-apps prtg smtp smtp-gmail-com

Created on Mar 21, 2010 9:08:09 AM by  candlebox1369 (1) 1

Last change on May 19, 2022 7:59:58 AM by  Luciano Lingnau [Paessler]



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This article applies as of PRTG 22

How to use a Gmail address for SMTP delivery


Important: As of May 30, 2022, third-party apps and devices can no longer use a user name and password to log in to your Google Account. If you want to use a Gmail address for SMTP delivery as of May 30, 2022, an application password is required. For more information, see Less secure apps & your Google Account.


If you want to use a Gmail address for SMTP delivery, meet the requirements and follow the instructions below.

Requirements

  • A Gmail business account (Google Workspace) or free Gmail account.
  • 2-Step Verification must be enabled for the Gmail account that is used as SMTP Relay. For more information, see Turn on 2-Step Verification.
  • The firewall settings on the PRTG core server system must allow connections on port 465 or 587.

Enter Gmail notification delivery settings in PRTG

Note: As reference, you can see the configuration with the user name johnqpublic below. Adjust the settings according to your configuration if required.

  1. In the PRTG web interface, select Setup | System Administration | Notification Delivery from the main menu.
  2. Enter the required information and click Test SMTP Settings if you want to test the configuration or click Save to directly save your settings.

SMTP Delivery Settings
Click to enlarge

Delivery MechanismUse one SMTP relay server (recommended in LANs/NATs)
Sender Email Address[email protected]
Sender NamePRTG Network Monitor
HELO Identprtgserver.domain.tld (optional - make sure that it has no space in it.)
SMTP Relay Serversmtp.gmail.com
SMTP Relay Port587 or 465
SMTP Relay AuthenticationUse standard SMTP authentication
SMTP Relay User Name[email protected]
SMTP Relay PasswordEnter the Google app password. For more information, see the second Note below.
Connection SecurityUse SSL/TLS if the server supports it
SSL MethodTLS 1.2

Notes:

  • Make sure you replace johnqpublic in the email address that you use as Sender Email Address and SMTP Relay User Name with your own Gmail user name. If you use a Google Workspace account, enter [email protected] as Sender Email Address and SMTP Relay User Name instead.
  • For more information, about how to create an application password, see Sign in with App Passwords.

Troubleshooting

To test the new settings, open Setup | Account Settings | Notification Templates in the PRTG web interface, select an email notification, and click Test SMTP Settings. PRTG tries to send an email immediately.

If you have any problems sending emails, please check the Logs for respective entries. Make sure that your firewall settings allow a connection on port 465 or 587.

More

Created on May 18, 2022 12:30:22 PM by  Florian Weik [Paessler Support]

Last change on Jun 29, 2022 7:10:57 AM by  Brandy Greger [Paessler Support]



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This article applies to PRTG Network Monitor 7

We actually managed to get a GMail / Googlemail account to relay notification mails using the following settings:

OptionSetting
SMTP relay serversmtp.gmail.com
SMTP relay port465
SMTP Relay AuthenticationUse standard SMTP authentication
Use TLSon

Please also see Configuring other mail clients from GMail help.

Created on Mar 22, 2010 10:56:44 AM by  Patrick Hutter [Paessler Support] (7,225) 3 3

Last change on Jun 14, 2011 9:07:26 AM by  Daniel Zobel [Product Manager]



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Tried it and worked. Thanks.

Created on Mar 24, 2010 1:54:11 AM by  candlebox1369 (1) 1



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Hi, We have just recently installed prtg and we still can't send out notifications. Even after changing to the above settings we still get the 'Error sending "Email": Connection failed ("smtp.gmail.com")" message. I have left the HELO Ident with the default settings -WIN-JN6NM66AF2G. Not sure if this is the reason for this. Hope you can shed some light.

Created on Jun 9, 2011 3:47:42 AM by  amirhussin (0)



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Currently running PRTG Network Monitor 13. Tried to use my Gmail account based on the information supplied above for "Setting for PRTG 9" but it continued to fail.

After researching it a bit further, found that there is another port "587" that can be used for the SMTP Relay SMTP port. Updated new port, saved changes, tested and received the notification as desired.

Created on Mar 20, 2013 12:51:22 PM by  ppatullo (0)



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@ppatullo: Thank you for the information!

Created on Mar 20, 2013 12:53:09 PM by  Konstantin Wolff [Paessler Support]



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Hi Paessler Support,

I have configured as per above recommendation, but still negative result.

Could you please advise.

PRTG version: 15.4.21.5481+ Trial Version PRTG Version: 15.3.17.2996+ Commercial License

Regards, Jovan

Created on Dec 30, 2015 7:27:15 AM by  jovan (0)



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Hi Jovan,

Which exact error message do you receive within PRTG? We recently ran into this error ourselves and found that you would have to enable option  "Allow less secure apps" in your gmail settings at this page.

This is currently the only way to get an POP/IMAP sensor to connect.

You will also need to white-list the PRTG server to use the GMail account as a relay server. The configuration is described on this page.

Best regards, Felix

Created on Dec 30, 2015 8:55:37 AM by  Felix Saure [Paessler Support]



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Hi Felix,

I will try.

Meanwhile, could you please advise where can i extract relevant information and send it to you?

Warmest regards, Jovan

Created on Dec 30, 2015 4:37:12 PM by  jovan (0)



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Hi Jovan,

You can write an email to [email protected], this will create a support ticket and me or one of my colleagues will answer your inquiry by email.

Best regards, Felix

Created on Dec 31, 2015 8:59:01 AM by  Felix Saure [Paessler Support]



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Thank you! Port 587 works for me.

Created on May 5, 2017 1:27:08 PM by  hatula (0)



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I have just tested the PRTG Mail Delivery using Google Apps (aka G-Suite) (should be the same for plain gmail accounts). This is what the set-up should look like:

SMTP Delivery Mechanism:Use SMTP relay server
Sender Email:[email protected]
Sender Name:PRTG
HELO ident:prtgserver.domain.tld(optional)
SMTP Relay Server:smtp.gmail.com
SMTP Relay SMTP Port:587
SMTP Relay Authentication:Use standard SMTP authentication
SMTP Relay User:[email protected]
Use Encrypted Connection:If supported by server
SSL Method:'TLS v1.2'

It's also very important to note that you need to change a setting for the Gmail/Google Apps account that you want to use for mail sending over SMTP. The setting is called Allow less secure apps and is described in this page. Here's the link to change the settings for your Google Mail account:

Even with everything set-up correctly in PRTG you will receive the following error if you don't allow the "less secure apps":

Error sending "Email": Authentication unsuccessful ("smtp.gmail.com")



Messages were sent successfully in PRTG Version 17.4.33.3251 with the set-up above.


Alternative: If you have two factor authentication (2FA) activated for your Google account, there is an alternative to the Allow less secure apps setting: Generate a dedicated app password for PRTG as described in this page. Here's the link to add an app password in the settings of your Google account:

Messages were also sent successfully in PRTG Version 17.4.33.3251 using a per-app password with a 2FA account.



Best Regards,
Luciano Lingnau [Paessler Support]

Created on Nov 8, 2017 7:54:20 AM by  Luciano Lingnau [Paessler]

Last change on Nov 9, 2017 2:46:51 PM by  Gerald Schoch [Paessler Support]



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Enabling access for "less secure apps" means that the client/app doesn't use OAuth 2.0 . OAuth 2.0 is the industry-standard protocol for authorization. When you sign in with OAuth 2.0, you sign in to Google's system directly. In OAuth 2.0 , you authenticate directly to Gmail with your credentials and authorize an app to do certain things. The third-party app only sees an authorization token provided by Google as proof that you authenticated correctly and agreed to authorize that app.

Created on Jul 31, 2019 6:09:15 AM by  markfilan (0)



Accepted Answer

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This article applies as of PRTG 22

How to use a Gmail address for SMTP delivery


Important: As of May 30, 2022, third-party apps and devices can no longer use a user name and password to log in to your Google Account. If you want to use a Gmail address for SMTP delivery as of May 30, 2022, an application password is required. For more information, see Less secure apps & your Google Account.


If you want to use a Gmail address for SMTP delivery, meet the requirements and follow the instructions below.

Requirements

  • A Gmail business account (Google Workspace) or free Gmail account.
  • 2-Step Verification must be enabled for the Gmail account that is used as SMTP Relay. For more information, see Turn on 2-Step Verification.
  • The firewall settings on the PRTG core server system must allow connections on port 465 or 587.

Enter Gmail notification delivery settings in PRTG

Note: As reference, you can see the configuration with the user name johnqpublic below. Adjust the settings according to your configuration if required.

  1. In the PRTG web interface, select Setup | System Administration | Notification Delivery from the main menu.
  2. Enter the required information and click Test SMTP Settings if you want to test the configuration or click Save to directly save your settings.

SMTP Delivery Settings
Click to enlarge

Delivery MechanismUse one SMTP relay server (recommended in LANs/NATs)
Sender Email Address[email protected]
Sender NamePRTG Network Monitor
HELO Identprtgserver.domain.tld (optional - make sure that it has no space in it.)
SMTP Relay Serversmtp.gmail.com
SMTP Relay Port587 or 465
SMTP Relay AuthenticationUse standard SMTP authentication
SMTP Relay User Name[email protected]
SMTP Relay PasswordEnter the Google app password. For more information, see the second Note below.
Connection SecurityUse SSL/TLS if the server supports it
SSL MethodTLS 1.2

Notes:

  • Make sure you replace johnqpublic in the email address that you use as Sender Email Address and SMTP Relay User Name with your own Gmail user name. If you use a Google Workspace account, enter [email protected] as Sender Email Address and SMTP Relay User Name instead.
  • For more information, about how to create an application password, see Sign in with App Passwords.

Troubleshooting

To test the new settings, open Setup | Account Settings | Notification Templates in the PRTG web interface, select an email notification, and click Test SMTP Settings. PRTG tries to send an email immediately.

If you have any problems sending emails, please check the Logs for respective entries. Make sure that your firewall settings allow a connection on port 465 or 587.

More

Created on May 18, 2022 12:30:22 PM by  Florian Weik [Paessler Support]

Last change on Jun 29, 2022 7:10:57 AM by  Brandy Greger [Paessler Support]



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Disclaimer: The information in the Paessler Knowledge Base comes without warranty of any kind. Use at your own risk. Before applying any instructions please exercise proper system administrator housekeeping. You must make sure that a proper backup of all your data is available.