I’m having problems when sending emails with attachments through linux using Javamail on Tomcat

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Asked: June 2, 20262026-06-02T22:31:56+00:00 2026-06-02T22:31:56+00:00

I’m having problems when sending emails with attachments through linux using Javamail on Tomcat

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I’m having problems when sending emails with attachments through linux using Javamail on Tomcat 6.0 .

When sending mails using Tomcat server on my machine (Windows 7 64), it works fine. I have tested it with both local smtp server and a gmail account as a relay. But when the mail is sent by my remote Tomcat server, which runs linux, the received mail is a mess, without subject, the attachment is shown as text(the original is a pdf file) and some mail headers comes mixed with the message. I have tried using the same approach that I used when testing on Windows: trying a local smtp server and then using the gmail as a relay. It didn’t works in neither cases.

I have also tried to change my local JavaMail libs, and use the same we have on the remote server(copied from the server to my machine), but the results running local are always the same. The email is received in the way it is expected.

When I send the email, it is sent another copy to me, so I can keep track of what is going on. In the log below is shown Javamail output for both mails(the original and the copy) when running local tests using the Javamail that is embedded in my j2ee.jar (See below for further details):

DEBUG: setDebug: JavaMail version 1.3.1
DEBUG: getProvider() returning javax.mail.Provider[TRANSPORT,smtp,com.sun.mail.smtp.SMTPTransport,Sun Microsystems, Inc]
DEBUG SMTP: useEhlo true, useAuth true
DEBUG SMTP: useEhlo true, useAuth true
DEBUG SMTP: trying to connect to host "smtp.gmail.com", port 587

220 mx.google.com ESMTP jz16sm6498879vdb.9
DEBUG SMTP: connected to host "smtp.gmail.com", port: 587

EHLO Felipe-HP
250-mx.google.com at your service, [177.17.162.156]
250-SIZE 35882577
250-8BITMIME
250-AUTH LOGIN PLAIN XOAUTH
250-ENHANCEDSTATUSCODES
250 STARTTLS
DEBUG SMTP: Found extension "SIZE", arg "35882577"
DEBUG SMTP: Found extension "8BITMIME", arg ""
DEBUG SMTP: Found extension "AUTH", arg "LOGIN PLAIN XOAUTH"
DEBUG SMTP: Found extension "ENHANCEDSTATUSCODES", arg ""
DEBUG SMTP: Found extension "STARTTLS", arg ""
DEBUG SMTP: Attempt to authenticate
AUTH LOGIN
334 xxxxxxxxx
334 xxxxxxxxx
235 2.7.0 Accepted
DEBUG SMTP: use8bit false
MAIL FROM:< xxxxx@xxxxx.xxxx.xxxx>
250 2.1.0 OK jz16sm6498879vdb.9
RCPT TO:< xxxxx@xxxxx.xxxx.xxxx>
250 2.1.5 OK jz16sm6498879vdb.9
DEBUG SMTP: Verified Addresses
DEBUG SMTP:    xxxxx@xxxxx.xxxx.xxxx
DATA
354  Go ahead jz16sm6498879vdb.9
Message-ID: <38047647.1335464129114.JavaMail.Felipe@Felipe-HP>
From:  xxxxx@xxxxx.xxxx.xxxx
To:  xxxxx@xxxxx.xxxx.xxxx
Subject: Boleto Amaua - 06/05/2012
Mime-Version: 1.0
Content-Type: multipart/mixed; 
    boundary="----=_Part_0_1451495453.1335464128994"

------=_Part_0_1451495453.1335464128994
Content-Type: text/plain; charset=ISO-8859-1
Content-Transfer-Encoding: quoted-printable
Content-Disposition: inline



------=_Part_0_1451495453.1335464128994
Content-Type: application/octet-stream; 
    name=boleto-158-255-1335464128903.pdf
Content-Transfer-Encoding: base64
Content-Disposition: attachment; filename=boleto-158-255-1335464128903.pdf
Content-Description: Attached file: boleto-158-255-1335464128903.pdf



------=_Part_0_1451495453.1335464128994--

.
250 2.0.0 OK 1335464133 jz16sm6498879vdb.9
QUIT








DEBUG: setDebug: JavaMail version 1.3.1
DEBUG: getProvider() returning javax.mail.Provider[TRANSPORT,smtp,com.sun.mail.smtp.SMTPTransport,Sun Microsystems, Inc]
DEBUG SMTP: useEhlo true, useAuth true
DEBUG SMTP: useEhlo true, useAuth true
DEBUG SMTP: trying to connect to host "smtp.gmail.com", port 587

220 mx.google.com ESMTP jz16sm6499184vdb.9
DEBUG SMTP: connected to host "smtp.gmail.com", port: 587

EHLO Felipe-HP
250-mx.google.com at your service, [177.17.162.156]
250-SIZE 35882577
250-8BITMIME
250-AUTH LOGIN PLAIN XOAUTH
250-ENHANCEDSTATUSCODES
250 STARTTLS
DEBUG SMTP: Found extension "SIZE", arg "35882577"
DEBUG SMTP: Found extension "8BITMIME", arg ""
DEBUG SMTP: Found extension "AUTH", arg "LOGIN PLAIN XOAUTH"
DEBUG SMTP: Found extension "ENHANCEDSTATUSCODES", arg ""
DEBUG SMTP: Found extension "STARTTLS", arg ""
DEBUG SMTP: Attempt to authenticate
AUTH LOGIN
334 xxxxxxxxxx
334 xxxxxxxxxx
235 2.7.0 Accepted
DEBUG SMTP: use8bit false
MAIL FROM:< xxxxx@xxxxx.xxxx.xxxx>
250 2.1.0 OK jz16sm6499184vdb.9
RCPT TO:< xxxxx@xxxxx.xxxx.xxxx>
250 2.1.5 OK jz16sm6499184vdb.9
DEBUG SMTP:  xxxxx@xxxxx.xxxx.xxxx
DEBUG SMTP:    xxxxx@xxxxx.xxxx.xxxx
DATA
354  Go ahead jz16sm6499184vdb.9
Message-ID: <895165784.1335464133437.JavaMail.Felipe@Felipe-HP>
From:  xxxxx@xxxxx.xxxx.xxxx
To:  xxxxx@xxxxx.xxxx.xxxx
Subject: =?ISO-8859-1?Q?C=F3pia_Boleto_Amaua_-_06/05/2012?=
Mime-Version: 1.0
Content-Type: multipart/mixed; 
    boundary="----=_Part_1_1973765399.1335464133435"

------=_Part_1_1973765399.1335464133435
Content-Type: text/plain; charset=ISO-8859-1
Content-Transfer-Encoding: quoted-printable
Content-Disposition: inline

###################################################################
Mail Content
###################################################################

------=_Part_1_1973765399.1335464133435
Content-Type: application/octet-stream; 
    name=boleto-158-255-1335464128903.pdf
Content-Transfer-Encoding: base64
Content-Disposition: attachment; filename=boleto-158-255-1335464128903.pdf
Content-Description: Attached file: boleto-158-255-1335464128903.pdf


##################################################################
Attachment content
##################################################################

------=_Part_1_1973765399.1335464133435--

.
250 2.0.0 OK 1335464137 jz16sm6499184vdb.9
QUIT

Below is shown the log generate by my server:

Loading javamail.default.providers from jar:file:/opt/tomcat60/lib/mail.jar!/META-INF/javamail.default.providers
DEBUG: loading new provider protocol=imap, className=com.sun.mail.imap.IMAPStore, vendor=Sun Microsystems, Inc, version=null
DEBUG: loading new provider protocol=imaps, className=com.sun.mail.imap.IMAPSSLStore, vendor=Sun Microsystems, Inc, version=null
DEBUG: loading new provider protocol=smtp, className=com.sun.mail.smtp.SMTPTransport, vendor=Sun Microsystems, Inc, version=null
DEBUG: loading new provider protocol=smtps, className=com.sun.mail.smtp.SMTPSSLTransport, vendor=Sun Microsystems, Inc, version=null
DEBUG: loading new provider protocol=pop3, className=com.sun.mail.pop3.POP3Store, vendor=Sun Microsystems, Inc, version=null
DEBUG: loading new provider protocol=pop3s, className=com.sun.mail.pop3.POP3SSLStore, vendor=Sun Microsystems, Inc, version=null

Loading javamail.default.providers from jar:file:/home/xxxxxxx/public_html/WEB-INF/lib/mail.jar!/META-INF/javamail.default.providers
DEBUG: loading new provider protocol=imap, className=com.sun.mail.imap.IMAPStore, vendor=Sun Microsystems, Inc, version=null
DEBUG: loading new provider protocol=imaps, className=com.sun.mail.imap.IMAPSSLStore, vendor=Sun Microsystems, Inc, version=null
DEBUG: loading new provider protocol=smtp, className=com.sun.mail.smtp.SMTPTransport, vendor=Sun Microsystems, Inc, version=null
DEBUG: loading new provider protocol=smtps, className=com.sun.mail.smtp.SMTPSSLTransport, vendor=Sun Microsystems, Inc, version=null
DEBUG: loading new provider protocol=pop3, className=com.sun.mail.pop3.POP3Store, vendor=Sun Microsystems, Inc, version=null
DEBUG: loading new provider protocol=pop3s, className=com.sun.mail.pop3.POP3SSLStore, vendor=Sun Microsystems, Inc, version=null
DEBUG: getProvider() returning provider protocol=smtp; type=javax.mail.Provider$Type@67aece; class=com.sun.mail.smtp.SMTPTransport; vendor=Sun Microsystems, Inc

DEBUG SMTP: useEhlo true, useAuth true
DEBUG SMTP: useEhlo true, useAuth true
DEBUG SMTP: trying to connect to host "smtp.gmail.com", port 587, isSSL false
220 mx.google.com ESMTP dc7sm2927045vdc.6
DEBUG SMTP: connected to host "smtp.gmail.com", port: 587

EHLO l50dnn0358.locaweb.com.br
250-mx.google.com at your service, [187.45.198.10]
250-SIZE 35882577
250-8BITMIME
250-STARTTLS
250-ENHANCEDSTATUSCODES
250 PIPELINING
DEBUG SMTP: Found extension "SIZE", arg "35882577"
DEBUG SMTP: Found extension "8BITMIME", arg ""
DEBUG SMTP: Found extension "STARTTLS", arg ""
DEBUG SMTP: Found extension "ENHANCEDSTATUSCODES", arg ""
DEBUG SMTP: Found extension "PIPELINING", arg ""
STARTTLS
220 2.0.0 Ready to start TLS
EHLO l50dnn0358.locaweb.com.br
250-mx.google.com at your service, [187.45.198.10]
250-SIZE 35882577
250-8BITMIME
250-AUTH LOGIN PLAIN XOAUTH
250-ENHANCEDSTATUSCODES
250 PIPELINING
DEBUG SMTP: Found extension "SIZE", arg "35882577"
DEBUG SMTP: Found extension "8BITMIME", arg ""
DEBUG SMTP: Found extension "AUTH", arg "LOGIN PLAIN XOAUTH"
DEBUG SMTP: Found extension "ENHANCEDSTATUSCODES", arg ""
DEBUG SMTP: Found extension "PIPELINING", arg ""
DEBUG SMTP: Attempt to authenticate
DEBUG SMTP: check mechanisms: LOGIN PLAIN DIGEST-MD5 NTLM 
DEBUG SMTP: AUTH LOGIN command trace suppressed
DEBUG SMTP: AUTH LOGIN succeeded
DEBUG SMTP: use8bit false
MAIL FROM:<xxxxx@xxxxx.xxxx.xxxx>
250 2.1.0 OK dc7sm2927045vdc.6
RCPT TO:<xxxxx@xxxxx.xxxx.xxxx>
250 2.1.5 OK dc7sm2927045vdc.6
DEBUG SMTP: Verified Addresses
DEBUG SMTP:   xxxxx@xxxxx.xxxx.xxxx
DATA
354  Go ahead dc7sm2927045vdc.6

------=_Part_0_16475596.1335412817148
Content-Type: text/plain; charset=ISO-8859-1
Content-Transfer-Encoding: quoted-printable
Content-Disposition: inline

###################################################################
Mail Content
###################################################################

------=_Part_0_16475596.1335412817148
Content-Type: application/octet-stream; name=boleto-1436-1707-1335412817075.pdf
Content-Transfer-Encoding: base64
Content-Disposition: attachment; filename=boleto-1436-1707-1335412817075.pdf
Content-Description: Attached file: boleto-1436-1707-1335412817075.pdf

##################################################################
Attachment content
##################################################################

------=_Part_0_16475596.1335412817148--
.
250 2.0.0 OK 1335412824 dc7sm2927045vdc.6
QUIT
221 2.0.0 closing connection dc7sm2927045vdc.6









DEBUG: getProvider() returning provider protocol=smtp; type=javax.mail.Provider$Type@67aece; class=com.sun.mail.smtp.SMTPTransport; vendor=Sun Microsystems, Inc
DEBUG SMTP: useEhlo true, useAuth true
DEBUG SMTP: useEhlo true, useAuth true
DEBUG SMTP: trying to connect to host "smtp.gmail.com", port 587, isSSL false
220 mx.google.com ESMTP c17sm2919516vdj.12
DEBUG SMTP: connected to host "smtp.gmail.com", port: 587

EHLO l50dnn0358.locaweb.com.br
250-mx.google.com at your service, [187.45.198.10]
250-SIZE 35882577
250-8BITMIME
250-STARTTLS
250-ENHANCEDSTATUSCODES
250 PIPELINING
DEBUG SMTP: Found extension "SIZE", arg "35882577"
DEBUG SMTP: Found extension "8BITMIME", arg ""
DEBUG SMTP: Found extension "STARTTLS", arg ""
DEBUG SMTP: Found extension "ENHANCEDSTATUSCODES", arg ""
DEBUG SMTP: Found extension "PIPELINING", arg ""
STARTTLS
220 2.0.0 Ready to start TLS
EHLO l50dnn0358.locaweb.com.br
250-mx.google.com at your service, [187.45.198.10]
250-SIZE 35882577
250-8BITMIME
250-AUTH LOGIN PLAIN XOAUTH
250-ENHANCEDSTATUSCODES
250 PIPELINING
DEBUG SMTP: Found extension "SIZE", arg "35882577"
DEBUG SMTP: Found extension "8BITMIME", arg ""
DEBUG SMTP: Found extension "AUTH", arg "LOGIN PLAIN XOAUTH"
DEBUG SMTP: Found extension "ENHANCEDSTATUSCODES", arg ""
DEBUG SMTP: Found extension "PIPELINING", arg ""
DEBUG SMTP: Attempt to authenticate
DEBUG SMTP: check mechanisms: LOGIN PLAIN DIGEST-MD5 NTLM 
DEBUG SMTP: AUTH LOGIN command trace suppressed
DEBUG SMTP: AUTH LOGIN succeeded
DEBUG SMTP: use8bit false
MAIL FROM:<xxxxxxx@xxxxx.xxxx.xxxx>
250 2.1.0 OK c17sm2919516vdj.12
RCPT TO:<xxxxx@xxxxx.xxxx.xxxx>
250 2.1.5 OK c17sm2919516vdj.12
DEBUG SMTP: Verified Addresses
DEBUG SMTP:   xxxxx@xxxxx.xxxx.xxxx
DATA
354  Go ahead c17sm2919516vdj.12

------=_Part_1_22662950.1335412824767
Content-Type: text/plain; charset=ISO-8859-1
Content-Transfer-Encoding: quoted-printable
Content-Disposition: inline

###################################################################
Mail Content
###################################################################

------=_Part_1_22662950.1335412824767
Content-Type: application/octet-stream; name=boleto-1436-1707-1335412817075.pdf
Content-Transfer-Encoding: base64
Content-Disposition: attachment; filename=boleto-1436-1707-1335412817075.pdf
Content-Description: Attached file: boleto-1436-1707-1335412817075.pdf

##################################################################
Attachment content
##################################################################

------=_Part_1_22662950.1335412824767--
.
250 2.0.0 OK 1335412828 c17sm2919516vdj.12
QUIT
221 2.0.0 closing connection c17sm2919516vdj.12

In my remote server, we have the JavaMail libs on the context/WEB-INF/lib. Where we have a mail.jar and a j2ee.jar which also contains the JavaMail. Also, in the tomcat folder there is another mail.jar(as can be seen on the logs) and another j2ee.jar that contains the Javamail.

I have tried replacing server’s /WEB-INF/lib/mail.jar with a recent one but the log didn’t even changes. And using the .jars from the server in my local tests produce the correct results.

Please, note that my server don’t show some debugs lines that should be present.

Below is the code used to send the email:

Properties props = new Properties();
props.put("mail.smtp.debug", "true");
props.put("mail.smtp.auth", "true");
props.put("mail.mime.charset", "ISO-8859-1"); 
props.put("mail.smtp.starttls.enable", "true");
props.put("mail.smtp.starttls.required", "true");
props.put("mail.smtp.host", smtpHost);
props.put("mail.smtp.port", Integer.toString(port));
this.session = Session.getInstance(props,
    new javax.mail.Authenticator() {
      protected PasswordAuthentication getPasswordAuthentication() {
         return new PasswordAuthentication(usr, pass);
      }
});

MimeMultipart mp = new MimeMultipart("mixed");
MimeBodyPart txtPart = new MimeBodyPart();

if(this.message == null){
    if(this.session != null){
       this.message = new MimeMessage(this.session);
    } else {
       throw new Exception("");
    }
}

this.session.setDebug(true);
this.message.setFrom(new InternetAddress(this.from));
this.message.setRecipient(Message.RecipientType.TO, new InternetAddress(this.to));
this.message.setSubject(this.subject);

txtPart.setDisposition(Part.INLINE);
txtPart.setText(text);
mp.addBodyPart(txtPart);

for (int i = 0; i < this.attach.size(); i++) {
    MimeBodyPart filePart = new MimeBodyPart();
    File file = (File) this.attach.elementAt(i);
    FileDataSource fds = new FileDataSource(file);
    DataHandler dh = new DataHandler(fds);
    filePart.setFileName(file.getName());
    filePart.setDisposition(Part.ATTACHMENT);
    filePart.setDescription("Attached file: " + file.getName());
    filePart.setDataHandler(dh);
    mp.addBodyPart(filePart);
}

this.message.setContent(mp);

Transport.send(this.message);

Any further detail needed, please ask.

Thanks for your consideration!

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1 Answer

Editorial Team · Answer 1 · 2026-06-02T22:31:57+00:00

Editorial Team

2026-06-02T22:31:57+00:00Added an answer on June 2, 2026 at 10:31 pm

Try removing j2ee.jar from your application; that contains a very old version of some of the JavaMail classes, which may be conflicting with the newer versions in mail.jar.

(j2ee.jar is only intended as something to be used at compilation time; it should never be used at runtime.)

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