Error in sending email through Gmail by using mailR

Question

I am trying to send an email from RStudio using mailR package and gmail. The following is my code...

library(mailR)
sender <- "[email protected]"
recipients <- c("[email protected]")
send.mail(from = sender,
          to = recipients,
          subject = "Test mail from Rstudio",
          body = "Test email body",
          smtp = list(host.name = "smtp.gmail.com", port = 465, 
                      user.name = "[email protected]",            
                      passwd = "******", ssl = TRUE),
          authenticate = TRUE,
          send = TRUE)

I get the following error message...

org.apache.commons.mail.EmailException: Sending the email to the following server failed : smtp.gmail.com:465
    at org.apache.commons.mail.Email.sendMimeMessage(Email.java:1410)
    at org.apache.commons.mail.Email.send(Email.java:1437)
    at sun.reflect.NativeMethodAccessorImpl.invoke0(Native Method)
    at sun.reflect.NativeMethodAccessorImpl.invoke(Unknown Source)
    at sun.reflect.DelegatingMethodAccessorImpl.invoke(Unknown Source)
    at java.lang.reflect.Method.invoke(Unknown Source)
    at RJavaTools.invokeMethod(RJavaTools.java:386)
Caused by: javax.mail.AuthenticationFailedException: 534-5.7.14 <https://accounts.google.com/signin/continue?sarp=1&scc=1&plt=AKgnsbuu
534-5.7.14 XIuKGOx55rNHFSvDWkzr2B1augfG-Z1zGTYEQ9IZ-iD_aDivhY0aUWNjt0C4ckYrqyx0WS
534-5.7.14 Zbz-1z65Xz8C1irD5crNwDSpgL3qQGgo6V-PvkiA6h1on6Hnn-YjSeho0uBWcG59x1C4TH
534-5.7.14 F6ZM2i2TToB9tIjzoUv_3encd3EW0Aw04XBaTVkoWseyUOaTTvglnCIj23ZNrIncqXW0f5
534-5.7.14 gjMKNtrSAOBmJxrgnXGrRS2BC9y9Q> Please log in via your web browser and
534-5.7.14 then try again.
534-5.7.14  Learn more at
534 5.7.14  https://support.google.com/mail/answer/78754 t62sm25604268pfa.38 - gsmtp

    at com.sun.mail.smtp.SMTPTransport$Authenticator.authenticate(SMTPTransport.java:892)
    at com.sun.mail.smtp.SMTPTransport.authenticate(SMTPTransport.java:814)
    at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:728)
    at javax.mail.Service.connect(Service.java:386)
    at javax.mail.Service.connect(Service.java:245)
    at javax.mail.Service.connect(Service.java:194)
    at javax.mail.Transport.send0(Transport.java:253)
    at javax.mail.Transport.send(Transport.java:124)
    at org.apache.commons.mail.Email.sendMimeMessage(Email.java:1400)
    ... 6 more
Error: EmailException (Java): Sending the email to the following server failed : smtp.gmail.com:465

What exactly I am doing wrong here? The google link mentioned in the error message doesn't exist.

EDIT: Got an email from google saying 'Sign-in attempt prevented: someone tried to sign in from an app that doesn't meet modern security standards... '

Is there a way around this? The google email doesn't say anything about allowing me to send message from R.

Answer 1

i have read through this and other threads carefully. i have the correct Java downloaded (64 bit), path to java env is correct, no 2FA set up on gmail, the "less secure app" access is on, yet neither through SSL + port 465 nor through TLS + port 587 am i able to send the email, i get this similar error to what's described above and in other question threads, those seem to be solved by either the 2FA issue or the "less secure app" issue - this one seems different... would really appreciate some help on this, already spent a good couple hours on it and going no where.

org.apache.commons.mail.EmailException: Sending the email to the following server failed : smtp.gmail.com:465
    at org.apache.commons.mail.Email.sendMimeMessage(Email.java:1410)
    at org.apache.commons.mail.Email.send(Email.java:1437)
    at sun.reflect.NativeMethodAccessorImpl.invoke0(Native Method)
    at sun.reflect.NativeMethodAccessorImpl.invoke(Unknown Source)
    at sun.reflect.DelegatingMethodAccessorImpl.invoke(Unknown Source)
    at java.lang.reflect.Method.invoke(Unknown Source)
    at RJavaTools.invokeMetNULL
hod(RJavaTools.java:386)
Caused by: javax.mail.MessagingException: Could not connect to SMTP host: smtp.gmail.com, port: 465;
  nested exception is:
    javax.net.ssl.SSLHandshakeException: No appropriate protocol (protocol is disabled or cipher suites are inappropriate)
    at com.sun.mail.smtp.SMTPTransport.openServer(SMTPTransport.java:2055)
    at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:697)
    at javax.mail.Service.connect(Service.java:386)
    at javax.mail.Service.connect(Service.java:245)
    at javax.mail.Service.connect(Service.java:194)
    at javax.mail.Transport.send0(Transport.java:253)
    at javax.mail.Transport.send(Transport.java:124)
    at org.apache.commons.mail.Email.sendMimeMessage(Email.java:1400)
    ... 6 more
Caused by: javax.net.ssl.SSLHandshakeException: No appropriate protocol (protocol is disabled or cipher suites are inappropriate)
    at sun.security.ssl.HandshakeContext.<init>(Unknown Source)
    at sun.security.ssl.ClientHandshakeContext.<init>(Unknown Source)
    at sun.security.ssl.TransportContext.kickstart(Unknown Source)
    at sun.security.ssl.SSLSocketImpl.startHandshake(Unknown Source)
    at sun.security.ssl.SSLSocketImpl.startHandshake(Unknown Source)
    at com.sun.mail.util.SocketFetcher.configureSSLSocket(SocketFetcher.java:543)
    at com.sun.mail.util.SocketFetcher.createSocket(SocketFetcher.java:348)
    at com.sun.mail.util.SocketFetcher.getSocket(SocketFetcher.java:215)
    at com.sun.mail.smtp.SMTPTransport.openServer(SMTPTransport.java:2019)
    ... 13 more
Error: EmailException (Java): Sending the email to the following server failed : smtp.gmail.com:465

Answer 2

Enable access to 'less secure apps' here:

http://www.google.com/settings/security/lesssecureapps