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  <title>SMTP configuration for Sendgrid</title>
  <link rel="self" href="https://liferay.dev/c/message_boards/find_thread?p_l_id=119785294&amp;threadId=118025219" />
  <subtitle>SMTP configuration for Sendgrid</subtitle>
  <id>https://liferay.dev/c/message_boards/find_thread?p_l_id=119785294&amp;threadId=118025219</id>
  <updated>2026-04-04T23:24:35Z</updated>
  <dc:date>2026-04-04T23:24:35Z</dc:date>
  <entry>
    <title>RE: SMTP configuration for Sendgrid</title>
    <link rel="alternate" href="https://liferay.dev/c/message_boards/find_message?p_l_id=119785294&amp;messageId=119044919" />
    <author>
      <name>Bangaru Raju Potnuru</name>
    </author>
    <id>https://liferay.dev/c/message_boards/find_message?p_l_id=119785294&amp;messageId=119044919</id>
    <updated>2020-04-27T14:11:46Z</updated>
    <published>2020-04-27T14:11:46Z</published>
    <summary type="html">Hi ,&lt;br /&gt; I am trying to configure SMTP settings to send out emails from portal(Liferay 7.0  GA2&lt;br /&gt;Here is the configuration I have done in portal-ext.properties file&lt;br /&gt;&lt;br /&gt;mail.session.mail.smtp.auth=true&lt;br /&gt;    mail.session.mail.smtp.host=smtp.sendgrid.net&lt;br /&gt;    mail.session.mail.smtp.password=**********( Generated API KEY)&lt;br /&gt;    mail.session.mail.smtp.port=587&lt;br /&gt;    mail.session.mail.smtp.user=apikey&lt;br /&gt;    mail.session.mail.store.protocol=smtps&lt;br /&gt;    mail.session.mail.transport.protocol=smtp&lt;br /&gt;    mail.smtp.starttls.enable=true&lt;br /&gt;    mail.transport.protocol=smtps&lt;br /&gt;&lt;br /&gt;I am getting the following error,thouugh im giving proper details.&lt;br /&gt;&lt;br /&gt;13:57:25,538 ERROR [liferay/mail-1][MailEngine:77] null&lt;br /&gt;javax.mail.AuthenticationFailedException&lt;br /&gt;    at javax.mail.Service.connect(Service.java:306)&lt;br /&gt;    at com.liferay.util.mail.MailEngine._send(MailEngine.java:554)&lt;br /&gt;    at com.liferay.util.mail.MailEngine.send(MailEngine.java:354)&lt;br /&gt;    at com.liferay.util.mail.MailEngine.send(MailEngine.java:429)&lt;br /&gt;    at com.liferay.mail.messaging.MailMessageListener.doMailMessage(MailMessageListener.java:94)&lt;br /&gt;    at com.liferay.mail.messaging.MailMessageListener.doReceive(MailMessageListener.java:109)&lt;br /&gt;    at com.liferay.portal.kernel.messaging.BaseMessageListener.receive(BaseMessageListener.java:26)&lt;br /&gt;    at com.liferay.portal.kernel.messaging.InvokerMessageListener.receive(InvokerMessageListener.java:74)&lt;br /&gt;    at com.liferay.portal.kernel.messaging.ParallelDestination$1.run(ParallelDestination.java:52)&lt;br /&gt;    at com.liferay.portal.kernel.concurrent.ThreadPoolExecutor$WorkerTask._runTask(ThreadPoolExecutor.java:756)&lt;br /&gt;    at com.liferay.portal.kernel.concurrent.ThreadPoolExecutor$WorkerTask.run(ThreadPoolExecutor.java:667)&lt;br /&gt;    at java.lang.Thread.run(Thread.java:745)&lt;br /&gt;&lt;br /&gt;&lt;br /&gt;Please help me out.Regards,&lt;br /&gt;Raju</summary>
    <dc:creator>Bangaru Raju Potnuru</dc:creator>
    <dc:date>2020-04-27T14:11:46Z</dc:date>
  </entry>
  <entry>
    <title>RE: SMTP configuration for Sendgrid</title>
    <link rel="alternate" href="https://liferay.dev/c/message_boards/find_message?p_l_id=119785294&amp;messageId=118025954" />
    <author>
      <name>Shruti Mishra</name>
    </author>
    <id>https://liferay.dev/c/message_boards/find_message?p_l_id=119785294&amp;messageId=118025954</id>
    <updated>2019-12-09T10:56:59Z</updated>
    <published>2019-12-09T10:56:59Z</published>
    <summary type="html">mail.transport.protocol=smtps   worked!!!&lt;br /&gt;Thank you Ankit</summary>
    <dc:creator>Shruti Mishra</dc:creator>
    <dc:date>2019-12-09T10:56:59Z</dc:date>
  </entry>
  <entry>
    <title>RE: SMTP configuration for Sendgrid</title>
    <link rel="alternate" href="https://liferay.dev/c/message_boards/find_message?p_l_id=119785294&amp;messageId=118025591" />
    <author>
      <name>Ankit Kulshrestha</name>
    </author>
    <id>https://liferay.dev/c/message_boards/find_message?p_l_id=119785294&amp;messageId=118025591</id>
    <updated>2019-12-09T10:29:40Z</updated>
    <published>2019-12-09T10:29:40Z</published>
    <summary type="html">Hi Shruti,&lt;br /&gt;&lt;br /&gt;Send Grid mail servers run on SMTPS protocols, if you change the mail.transport.protocol=smtp to mail.transport.protocol=smtps that should do the trick. Let me know if you need more information on this.&lt;br /&gt;&lt;br /&gt;Regards,&lt;br /&gt;&lt;br /&gt;Ankit Kulshrestha</summary>
    <dc:creator>Ankit Kulshrestha</dc:creator>
    <dc:date>2019-12-09T10:29:40Z</dc:date>
  </entry>
  <entry>
    <title>RE: SMTP configuration for Sendgrid</title>
    <link rel="alternate" href="https://liferay.dev/c/message_boards/find_message?p_l_id=119785294&amp;messageId=118027446" />
    <author>
      <name>Olaf Kock</name>
    </author>
    <id>https://liferay.dev/c/message_boards/find_message?p_l_id=119785294&amp;messageId=118027446</id>
    <updated>2019-12-09T09:59:01Z</updated>
    <published>2019-12-09T09:59:01Z</published>
    <summary type="html">&lt;div class="quote-title"&gt;Shruti Mishra:&lt;/div&gt;&lt;blockquote&gt;&lt;br /&gt;Hi,&lt;br /&gt;LR version 7.2 GA1&lt;br /&gt;We are trying to configure SMTP settings to send out emails from Form on portal.&lt;br /&gt;However, the emails are not sent with Authentication Error.&lt;br /&gt;&lt;/blockquote&gt;According to the &lt;a href="https://docs.liferay.com/portal/7.2-ga1/propertiesdoc/portal.properties.html#Mail"&gt;portal.properties documentation&lt;/a&gt;, those should be all. &lt;br /&gt;What you can do is: Alternatively configure a connection on your appserver, and make it available through mail.session.jndi.name - this way you can test the connection on the appserver, plus you&amp;#39;re not saving a cleartext password in Liferay&amp;#39;s configuration.&lt;br /&gt;Another idea: You&amp;#39;ve (correctly) masked out your password - make sure it doesn&amp;#39;t contain anything nasty for the properties-formatting: E.g. if the password ends in a backslash, that might signal a linebreak in the properties file, instead of the literal character. I&amp;#39;m also never sure if/how/when something like \t is expanded to the tab character. Let alone other non-ASCII characters.</summary>
    <dc:creator>Olaf Kock</dc:creator>
    <dc:date>2019-12-09T09:59:01Z</dc:date>
  </entry>
  <entry>
    <title>SMTP configuration for Sendgrid</title>
    <link rel="alternate" href="https://liferay.dev/c/message_boards/find_message?p_l_id=119785294&amp;messageId=118025218" />
    <author>
      <name>Shruti Mishra</name>
    </author>
    <id>https://liferay.dev/c/message_boards/find_message?p_l_id=119785294&amp;messageId=118025218</id>
    <updated>2019-12-09T07:33:51Z</updated>
    <published>2019-12-09T07:33:51Z</published>
    <summary type="html">Hi,&lt;br /&gt;LR version 7.2 GA1&lt;br /&gt;We are trying to configure SMTP settings to send out emails from Form on portal.&lt;br /&gt;However, the emails are not sent with Authentication Error.&lt;br /&gt;Below are settings in portal-ext.properties&lt;br /&gt;&lt;br /&gt;mail.session.mail.smtp.auth=true&lt;br /&gt;mail.session.mail.smtp.host=smtp.sendgrid.net&lt;br /&gt;mail.session.mail.smtp.password=********&lt;br /&gt;mail.session.mail.smtp.port=587&lt;br /&gt;mail.session.mail.smtp.user=something@azure.com&lt;br /&gt;mail.transport.protocol=smtp&lt;br /&gt;mail.smtp.starttls.enable=true&lt;br /&gt;Error Log&lt;br /&gt;2019-12-09 06:53:18.445 ERROR [liferay/mail-2][MailEngine:74] Unable to send message: null&lt;br /&gt;javax.mail.AuthenticationFailedException&lt;br /&gt;        at javax.mail.Service.connect(Service.java:306)&lt;br /&gt;        at javax.mail.Service.connect(Service.java:156)&lt;br /&gt;        at javax.mail.Service.connect(Service.java:105)&lt;br /&gt;        at javax.mail.Transport.send0(Transport.java:168)&lt;br /&gt;        at javax.mail.Transport.send(Transport.java:98)&lt;br /&gt;        at com.liferay.petra.mail.MailEngine._send(MailEngine.java:627)&lt;br /&gt;        at com.liferay.petra.mail.MailEngine.send(MailEngine.java:386)&lt;br /&gt;        at com.liferay.petra.mail.MailEngine.send(MailEngine.java:461)&lt;br /&gt;        at com.liferay.mail.messaging.MailMessageListener.doMailMessage(MailMessageListener.java:94)&lt;br /&gt;        at com.liferay.mail.messaging.MailMessageListener.doReceive(MailMessageListener.java:109)&lt;br /&gt;        at com.liferay.portal.kernel.messaging.BaseMessageListener.receive(BaseMessageListener.java:26)&lt;br /&gt;        at com.liferay.portal.kernel.messaging.InvokerMessageListener.receive(InvokerMessageListener.java:74)&lt;br /&gt;        at com.liferay.portal.kernel.messaging.ParallelDestination$1.run(ParallelDestination.java:52)&lt;br /&gt;        at com.liferay.portal.kernel.concurrent.ThreadPoolExecutor$WorkerTask._runTask(ThreadPoolExecutor.java:752)&lt;br /&gt;        at com.liferay.portal.kernel.concurrent.ThreadPoolExecutor$WorkerTask.run(ThreadPoolExecutor.java:664)&lt;br /&gt;        at java.lang.Thread.run(Thread.java:748)&lt;br /&gt;Am I missing something in the property file?&lt;br /&gt;&lt;br /&gt;Thanks .</summary>
    <dc:creator>Shruti Mishra</dc:creator>
    <dc:date>2019-12-09T07:33:51Z</dc:date>
  </entry>
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