mailR send.mail Java error on Mac OS High Sierra

Question

After upgrading macOS to High Sierra send.mail() from the mailR R package breaks due to a Java related issue. Before the OS upgrade the R code worked fine and there were no issues with the connection to smtp.gmail.com .

R Code:

library(mailR)

send.mail(from = "***@gmail.com",
      encoding= "utf-8",
      to = "***@gmail.com",
      subject = "my subject",
      body = "hello",
      smtp = list(host.name = "smtp.gmail.com",
                  port = 465,
                  user.name = "user",
                  passwd = "****",
                  ssl = TRUE),
      authenticate = TRUE,
      send = TRUE,
      debug = TRUE)

Error message:

Unexpected error: java.security.InvalidAlgorithmParameterException: the trustAnchors parameter must be non-empty

Complete prompt output:

DEBUG SMTP: trying to connect to host "smtp.gmail.com", port 465, isSSL 

false
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(NativeMethodAccessorImpl.java:39)
    at sun.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:25)
    at java.lang.reflect.Method.invoke(Method.java:597)
    at RJavaTools.invokeMethod(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.SSLException: java.lang.RuntimeException: Unexpected error: java.security.InvalidAlgorithmParameterException: the trustAnchors parameter must be non-empty
    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.SSLException: java.lang.RuntimeException: Unexpected error: java.security.InvalidAlgorithmParameterException: the trustAnchors parameter must be non-empty
    at com.sun.net.ssl.internal.ssl.Alerts.getSSLException(Alerts.java:190)
    at com.sun.net.ssl.internal.ssl.SSLSocketImpl.fatal(SSLSocketImpl.java:1747)
    at com.sun.net.ssl.internal.ssl.SSLSocketImpl.fatal(SSLSocketImpl.java:1708)
    at com.sun.net.ssl.internal.ssl.SSLSocketImpl.handleException(SSLSocketImpl.java:1691)
    at com.sun.net.ssl.internal.ssl.SSLSocketImpl.startHandshake(SSLSocketImpl.java:1222)
    at com.sun.net.ssl.internal.ssl.SSLSocketImpl.startHandshake(SSLSocketImpl.java:1199)
    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
Caused by: java.lang.RuntimeException: Unexpected error: java.security.InvalidAlgorithmParameterException: the trustAnchors parameter must be non-empty
    at sun.security.validator.PKIXValidator.<init>(PKIXValidator.java:57)
    at sun.security.validator.Validator.getInstance(Validator.java:161)
    at com.sun.net.ssl.internal.ssl.X509TrustManagerImpl.getValidator(X509TrustManagerImpl.java:108)
    at com.sun.net.ssl.internal.ssl.X509TrustManagerImpl.checkServerTrusted(X509TrustManagerImpl.java:204)
    at com.sun.net.ssl.internal.ssl.X509TrustManagerImpl.checkServerTrusted(X509TrustManagerImpl.java:249)
    at com.sun.net.ssl.internal.ssl.ClientHandshaker.serverCertificate(ClientHandshaker.java:1188)
    at com.sun.net.ssl.internal.ssl.ClientHandshaker.processMessage(ClientHandshaker.java:135)
    at com.sun.net.ssl.internal.ssl.Handshaker.processLoop(Handshaker.java:593)
    at com.sun.net.ssl.internal.ssl.Handshaker.process_record(Handshaker.java:529)
    at com.sun.net.ssl.internal.ssl.SSLSocketImpl.readRecord(SSLSocketImpl.java:943)
    at com.sun.net.ssl.internal.ssl.SSLSocketImpl.performInitialHandshake(SSLSocketImpl.java:1188)
    at com.sun.net.ssl.internal.ssl.SSLSocketImpl.startHandshake(SSLSocketImpl.java:1215)
    ... 18 more
Caused by: java.security.InvalidAlgorithmParameterException: the trustAnchors parameter must be non-empty
    at java.security.cert.PKIXParameters.setTrustAnchors(PKIXParameters.java:183)
    at java.security.cert.PKIXParameters.<init>(PKIXParameters.java:103)
    at java.security.cert.PKIXBuilderParameters.<init>(PKIXBuilderParameters.java:87)
    at sun.security.validator.PKIXValidator.<init>(PKIXValidator.java:55)
    ... 29 more
NULL
Error: EmailException (Java): Sending the email to the following server failed : smtp.gmail.com:465

OS version:

$ sw_vers
ProductName:    Mac OS X
ProductVersion: 10.13.3
BuildVersion:   17D47

Java version:

$ java -version
java version "1.6.0_65"
Java(TM) SE Runtime Environment (build 1.6.0_65-b14-468)
Java HotSpot(TM) 64-Bit Server VM (build 20.65-b04-468, mixed mode)

R version:

R version 3.3.2 (2016-10-31) -- "Sincere Pumpkin Patch"
Copyright (C) 2016 The R Foundation for Statistical Computing
Platform: x86_64-apple-darwin13.4.0 (64-bit)

R Java configuration:

$ R CMD javareconf
Java interpreter : /usr/bin/java
Java version     : 1.6.0_65
Java home path   : /Library/Java/JavaVirtualMachines/1.6.0.jdk/Contents/Home
Java compiler    : /usr/bin/javac
Java headers gen.: /usr/bin/javah
Java archive tool: /usr/bin/jar
System Java on macOS

trying to compile and link a JNI program 
detected JNI cpp flags    : -I/System/Library/Frameworks/JavaVM.framework/Headers
detected JNI linker flags : -framework JavaVM
/usr/local/opt/llvm/bin/clang -fopenmp -I/Library/Frameworks/R.framework/Resources/include -DNDEBUG -I/System/Library/Frameworks/JavaVM.framework/Headers -I/usr/local/opt/gettext/include -I/usr/local/opt/llvm/include    -fPIC  -g -O3 -Wall -pedantic -std=gnu99 -mtune=native -pipe -c conftest.c -o conftest.o
conftest.c:4:5: warning: 'JNI_CreateJavaVM' is deprecated [-Wdeprecated-declarations]
    JNI_CreateJavaVM(0, 0, 0);
    ^
/System/Library/Frameworks/JavaVM.framework/Headers/jni.h:1937:1: note: 'JNI_CreateJavaVM' has been explicitly marked deprecated here
JNI_CreateJavaVM(JavaVM **pvm, void **penv, void *args);
^
1 warning generated.
/usr/local/opt/llvm/bin/clang -fopenmp -dynamiclib -Wl,-headerpad_max_install_names -undefined dynamic_lookup -single_module -multiply_defined suppress -L/Library/Frameworks/R.framework/Resources/lib -L/usr/local/opt/gettext/lib -L/usr/local/opt/llvm/lib -Wl,-rpath,/usr/local/opt/llvm/lib -o conftest.so conftest.o -framework JavaVM -F/Library/Frameworks/R.framework/.. -framework R -Wl,-framework -Wl,CoreFoundation
ld: warning: directory not found for option '-L/usr/local/opt/gettext/lib'


JAVA_HOME        : /Library/Java/JavaVirtualMachines/1.6.0.jdk/Contents/Home
Java library path: 
JNI cpp flags    : -I/System/Library/Frameworks/JavaVM.framework/Headers
JNI linker flags : -framework JavaVM
Updating Java configuration in /Library/Frameworks/R.framework/Resources
Done.

Any help is appreciated!

Answer 1

I had the same problem. That is due to the package not being maintained anymore and changes in subsequent Java versions. As a solution, I can suggest gmailr package for GMail.