Mail goes offline when sending

I am helping a friend get his Mail working smoothly.
He accesses the internet with a dongle.  Safari works okay. However, when clicking Send in Mail, Mail goes into offline mode and shows a "~" icon. 
Anyone know how to get outgoing mail working.  Incoming seems to be working most of the time.
Andy

Try this. Upon waking the computer from sleep. Wait about 20 seconds before doing any network activity like Mail or Safari. Then try it.
When a computer goes to sleep, to the rest of the world, it is the same as being turned off. It's Internet connection is disconnected. It takes a few seconds to re-establish the connection.

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    * OK Gimap ready for requests from 74.75.90.3 x10if13064046qaa.18
    WROTE Jun 12 07:22:33.121 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x1987b7c0 -- thread:0x198636d0
    1.1147 CAPABILITY
    READ Jun 12 07:22:33.127 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:smtp.gmail.com -- port:465 -- socket:0x19875730 -- thread:0x19803e00
    220 mx.google.com ESMTP cz12sm2746446qab.5
    READ Jun 12 07:22:33.168 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x1987b7c0 -- thread:0x198636d0
    * CAPABILITY IMAP4rev1 UNSELECT IDLE NAMESPACE QUOTA ID XLIST CHILDREN X-GM-EXT-1 XYZZY SASL-IR AUTH=XOAUTH
    1.1147 OK Thats all she wrote! x10if13064046qaa.18
    WROTE Jun 12 07:22:33.174 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x1987b7c0 -- thread:0x198636d0
    2.1147 LOGIN <mail account1> ********
    WROTE Jun 12 07:22:33.266 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:smtp.gmail.com -- port:465 -- socket:0x19875730 -- thread:0x19803e00
    EHLO [192.168.1.132]
    READ Jun 12 07:22:33.314 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:smtp.gmail.com -- port:465 -- socket:0x19875730 -- thread:0x19803e00
    250-mx.google.com at your service, [74.75.90.3]
    250-SIZE 35882577
    250-8BITMIME
    250-AUTH LOGIN PLAIN XOAUTH
    250 ENHANCEDSTATUSCODES
    WROTE Jun 12 07:22:33.319 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:smtp.gmail.com -- port:465 -- socket:0x19875730 -- thread:0x19803e00
    READ Jun 12 07:22:33.540 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x1987b7c0 -- thread:0x198636d0
    * CAPABILITY IMAP4rev1 UNSELECT IDLE NAMESPACE QUOTA ID XLIST CHILDREN X-GM-EXT-1 UIDPLUS COMPRESS=DEFLATE
    2.1147 OK <mail account1>@gmail.com <my name> authenticated (Success)
    WROTE Jun 12 07:22:33.551 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x1987b7c0 -- thread:0x198636d0
    3.1147 CAPABILITY
    READ Jun 12 07:22:33.684 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x1987b7c0 -- thread:0x198636d0
    * CAPABILITY IMAP4rev1 UNSELECT IDLE NAMESPACE QUOTA ID XLIST CHILDREN X-GM-EXT-1 UIDPLUS COMPRESS=DEFLATE
    3.1147 OK Success
    WROTE Jun 12 07:22:33.692 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x1987b7c0 -- thread:0x198636d0
    4.1147 LIST "" ""
    READ Jun 12 07:22:33.804 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:smtp.gmail.com -- port:465 -- socket:0x19875730 -- thread:0x19803e00
    535-5.7.1 Username and Password not accepted. Learn more at
    535 5.7.1 http://support.google.com/mail/bin/answer.py?answer=14257 cz12sm2746446qab.5
    WROTE Jun 12 07:22:33.811 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:smtp.gmail.com -- port:465 -- socket:0x19875730 -- thread:0x19803e00
    QUIT
    READ Jun 12 07:22:33.832 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x1987b7c0 -- thread:0x198636d0
    * LIST (\Noselect) "/" "/"
    4.1147 OK Success
    WROTE Jun 12 07:22:33.840 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x1987b7c0 -- thread:0x198636d0
    5.1147 LOGOUT
    CONNECTED Jun 12 07:24:42.404 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x198449d0 -- thread:0x198007b0
    READ Jun 12 07:24:42.606 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x198449d0 -- thread:0x198007b0
    * OK Gimap ready for requests from 74.75.90.3 z5if22694176yhn.21
    WROTE Jun 12 07:24:42.618 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x198449d0 -- thread:0x187e8f90
    1.1161 CAPABILITY
    READ Jun 12 07:24:42.673 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x198449d0 -- thread:0x187e8f90
    * CAPABILITY IMAP4rev1 UNSELECT IDLE NAMESPACE QUOTA ID XLIST CHILDREN X-GM-EXT-1 XYZZY SASL-IR AUTH=XOAUTH
    1.1161 OK Thats all she wrote! z5if22694176yhn.21
    WROTE Jun 12 07:24:42.685 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x198449d0 -- thread:0x187e8f90
    2.1161 LOGIN <mail account2>@<domain2>.com ********
    READ Jun 12 07:24:43.233 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x198449d0 -- thread:0x187e8f90
    * CAPABILITY IMAP4rev1 UNSELECT IDLE NAMESPACE QUOTA ID XLIST CHILDREN X-GM-EXT-1 UIDPLUS COMPRESS=DEFLATE
    2.1161 OK <Mail account2>@<domain2>.com <my name> authenticated (Success)
    WROTE Jun 12 07:24:43.240 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x198449d0 -- thread:0x187e8f90
    3.1161 CAPABILITY
    READ Jun 12 07:24:43.697 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x198449d0 -- thread:0x187e8f90
    * CAPABILITY IMAP4rev1 UNSELECT IDLE NAMESPACE QUOTA ID XLIST CHILDREN X-GM-EXT-1 UIDPLUS COMPRESS=DEFLATE
    3.1161 OK Success
    WROTE Jun 12 07:24:43.710 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x198449d0 -- thread:0x187e8f90
    4.1161 LIST "" ""
    READ Jun 12 07:24:43.860 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x198449d0 -- thread:0x187e8f90
    * LIST (\Noselect) "/" "/"
    4.1161 OK Success
    WROTE Jun 12 07:24:43.868 [kCFStreamSocketSecurityLevelNegotiatedSSL]  -- host:imap.gmail.com -- port:993 -- socket:0x198449d0 -- thread:0x187e8f90
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