ICloud mail server - Unable To Send With Apple Mail client

OS X 10.10.2
Mail v 8.2
iCloud mail
I am still able to receive messages but suddenly unable to send. Messages stay stuck in Outbox.
Mail Connection Doctor reports no problems:
If I setup MS Outlook for Mac 2011 with this iCloud account, I am able to send and receive like a champ.
Once it starts working, is there a way to change the outgoing mail server to use SSL, i.e., turn SSL to "ON" ?

Yes, I did. It doesn't show up in the logs because, I'm unable to send a message - it goes to the outbox immediately. And this led me to the conclusion below.
And by the way, I did get in touch with Apple Support who went through a number of troubleshooting scripts (including trying to use GMail's mail servers) and ultimately had me reinstall OS X from scratch. None of this worked.
Now this problem of being unable to send mail via my iCloud account, from the Apple Mail client, started only around the end of Feb. What I finally figured was that iCloud mail was using random ports on my machine to invoke its SMTP port. Everytime I would disable the firewall on my router completely, iCloud mail was able to send just fine. Recall that incoming was (and still is) working fine. Anyway, I installed wireshark to ID the ports that were being used when the firewall was down. I set up triggers on my router to open these up, turned on the firewall, but it just isn't working. I will have to play around with wireshark and see if I can figure out what ports need to be opened. Unless you or someone else knows. If I figure it out, I will post it here. Mind you, that I need to figure out not only the source ports that need to access port 587 but also what the real target port is (because I don't think it is just 587 as Apple claims).
By the by, when I asked the Apple Technician (some guy who I was transferred to after 3 other people - the one who asked me to reinstall Yosemite) if there was a way to change the outgoing mail server to use SSL, i.e., turn SSL to "ON", he said no there wasn't and why would one need to secure the traffic to Apple's SMTP server anyway? Seriously?

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DEV -n EDEV 1 10' 'acrx -o comm,ruid,%cpu' '-t1 10 1' '-f -pfc /var/db/r*/com.apple.*.{BS,Bas,Es,J,OSXU,Rem,up}*.bom' '{/,}L*/Lo*/Diag* -type f -regex .\*[cgh] ! -name *ag \( -exec grep -lq "^Thread c" {} \; -exec printf \* \; -o -true \) -execdir stat -f:%Sc:%N -t%F {} \;|sort -t: -k2 |tail -n'${p[38]} '-L {/{S*/,},}L*/Lau* -type f' '-L /{S*/,}L*/StartupItems -type f -exec file {} +' '-L /S*/L*/{C*/Sec*A,E}* {/,}L*/{A*d,Ca*/*/Ex,Compon,Ex,In,iTu,Keyb,Mail/B,P*P,Qu*T,Scripti,Sec,Servi,Spo,Widg}* -type f -name Info.plist' '/usr/lib -type f -name *.dylib' `awk "${s[31]}"<<<${p[23]}` "/e*/{auto,{cron,fs}tab,hosts,{[lp],sy}*.conf,pam.d/*,ssh{,d}_config,*.local} {,/usr/local}/etc/periodic/*/* /L*/P*{,/*}/com.a*.{Bo,sec*.ap}*t /S*/L*/Lau*/*t .launchd.conf" list getenv /Library/Preferences/com.apple.alf\ globalstate --proxy '-n get default' -I --dns -getdnsservers\ "${p[N5]}" -getinfo\ "${p[N5]}" -P -m\ / '' -n1 '-R -l1 -n1 -o prt -stats command,uid,prt' '--regexp --only-files --files com.apple.pkg.*|sort|uniq' -kl -l -s\ / '-R -l1 -n1 -o mem -stats command,uid,mem' -i4TCP:0-1023 com.apple.dashboard\ layer-gadgets '-d /L*/Mana*/$USER&&echo On' '-app Safari WebKitDNSPrefetchingEnabled' );N1=${#c2[@]};for j in {0..9};do c2[N1+j]=SP${p[j]}DataType;done;N2=${#c2[@]};for j in 0 1;do c2[N2+j]="-n ' syscall::'${p[33+j]}':return { @out[execname,uid]=sum(arg0) } tick-10sec { trunc(@out,1);exit(0);} '";done;l=(Restricted\ files Hidden\ apps 'Elapsed time (s)' POST Battery Safari\ extensions Bad\ plists 'High file counts' User Heat System\ load boot\ args FileVault Diagnostic\ reports Log 'Free space (MiB)' 'Swap (MiB)' Activity 'CPU per process' Login\ hook 'I/O per process' Mach\ ports kexts Daemons Agents launchd Startup\ items Admin\ access Root\ access Bundles dylibs Apps Font\ issues Inserted\ dylibs Firewall Proxies DNS TCP/IP Wi-Fi Profiles Root\ crontab User\ crontab 'Global login items' 'User login items' Spotlight Memory Listeners Widgets Parental\ Controls Prefetching SATA );N3=${#l[@]};for i in 0 1 2;do l[N3+i]=${p[5+i]};done;N4=${#l[@]};for j in 0 1;do l[N4+j]="Current ${p[29+j]}stream data";done;A0() { id -G|grep -qw 80;v[1]=$?;((v[1]==0))&&sudo true;v[2]=$?;v[3]=`date +%s`;clear >&-;date '+Start time: %T %D%n';};for i in 0 1;do eval ' A'$((1+i))'() { v=` eval "${c1[$1]} ${c2[$2]}"|'${c1[30+i]}' "${s[$3]}" `;[[ "$v" ]];};A'$((3+i))'() { v=` while read i;do [[ "$i" ]]&&eval "${c1[$1]} ${c2[$2]}" \"$i\"|'${c1[30+i]}' "${s[$3]}";done<<<"${v[$4]}" `;[[ "$v" ]];};A'$((5+i))'() { v=` while read i;do '${c1[30+i]}' "${s[$1]}" "$i";done<<<"${v[$2]}" `;[[ "$v" ]];};';done;A7(){ v=$((`date +%s`-v[3]));};B2(){ v[$1]="$v";};for i in 0 1;do eval ' B'$i'() { v=;((v['$((i+1))']==0))||{ v=No;false;};};B'$((3+i))'() { v[$2]=`'${c1[30+i]}' "${s[$3]}"<<<"${v[$1]}"`;} ';done;B5(){ v[$1]="${v[$1]}"$'\n'"${v[$2]}";};B6() { v=` paste -d: <(printf "${v[$1]}") <(printf "${v[$2]}")|awk -F: ' {printf("'"${f[$3]}"'",$1,$2)} ' `;};B7(){ v=`grep -Fv "${v[$1]}"<<<"$v"`;};C0(){ [[ "$v" ]]&&echo "$v";};C1() { [[ "$v" ]]&&printf "${f[$1]}" "${l[$2]}" "$v";};C2() { v=`echo $v`;[[ "$v" != 0 ]]&&C1 0 $1;};C3() { v=`sed -E "$s"<<<"$v"`&&C1 1 $1;};for i in 1 2;do for j in 2 3;do eval D$i$j'(){ A'$i' $1 $2 $3; C'$j' $4;};';done;done;{ A0;A2 0 $((N1+1)) 2;C0;A1 0 $N1 1;C0;B0;C2 27;B0&&! B1&&C2 28;D12 15 37 25 8;A1 0 $((N1+2)) 3;C0;D13 0 $((N1+3)) 4 3;D23 0 $((N1+4)) 5 4;D13 0 $((N1+9)) 59 50;for i in 0 1 2;do D13 0 $((N1+5+i)) 6 $((N3+i));done;D13 1 10 7 9;D13 1 11 8 10;D22 2 12 9 11;D12 3 13 10 12;D23 4 19 44 13;D23 5 14 12 14;D22 6 36 13 15;D22 7 37 14 16;D23 8 15 38 17;D22 9 16 16 18;B1&&{ D22 11 17 17 20;for i in 0 1;do D22 28 $((N2+i)) 45 $((N4+i));done;};D22 12 44 54 45;D22 12 39 15 21;A1 13 40 18;B2 4;B3 4 0 19;A3 14 6 32 0;B4 0 5 11;A1 17 41 20;B7 5;C3 22;B4 4 6 21;A3 14 7 32 6;B4 0 7 11;B3 4 0 22;A3 14 6 32 0;B4 0 8 11;B5 7 8;B1&&{ A2 19 26 23;B7 7;C3 23;};A2 18 26 23;B7 7;C3 24;A2 4 20 21;B7 6;B2 9;A4 14 7 52 9;B2 10;B6 9 10 4;C3 25;D13 4 21 24 26;B4 4 12 26;B3 4 13 27;A1 4 22 29;B7 12;B2 14;A4 14 6 52 14;B2 15;B6 14 15 4;B3 0 0 30;C3 29;A1 4 23 27;B7 13;C3 30;D13 24 24 32 31;D13 25 37 32 33;A2 23 18 28;B2 16;A2 16 25 33;B7 16;B3 0 0 34;B2 21;A6 47 21&&C0;B1&&{ D13 21 0 32 19;D13 10 42 32 40;D22 29 35 46 39;};D13 14 1 48 42;D12 34 43 53 44;D22 0 $((N1+8)) 51 32;D13 4 8 41 6;D12 26 28 35 34;D13 27 29 36 35;A2 27 32 39&&{ B2 19;A2 33 33 40;B2 20;B6 19 20 3;};C2 36;D23 33 34 42 37;B1&&D23 35 45 55 46;D23 32 31 43 38;D12 36 47 32 48;D13 20 42 32 41;D13 14 2 48 43;D13 4 5 32 1;D13 4 3 60 5;D12 26 48 49 49;B3 4 22 57;A1 26 46 56;B7 22;B3 0 0 58;C3 47;D22 4 4 50 0;D23 22 9 37 7;A7;C2 2;} 2>/dev/null|pbcopy;exit 2>&-
    Copy the selected text to the Clipboard by pressing the key combination command-C.
    7. Launch the built-in Terminal application in any of the following ways:
    ☞ Enter the first few letters of its name into a Spotlight search. Select it in the results (it should be at the top.)
    ☞ In the Finder, select Go ▹ Utilities from the menu bar, or press the key combination shift-command-U. The application is in the folder that opens.
    ☞ Open LaunchPad. Click Utilities, then Terminal in the icon grid.
    Click anywhere in the Terminal window and paste by pressing command-V. The text you pasted should vanish immediately. If it doesn't, press the return key.
    8. If you see an error message in the Terminal window such as "Syntax error" or "Event not found," enter
    exec bash
    and press return. Then paste the script again.
    9. If you're logged in as an administrator, you'll be prompted for your login password. Nothing will be displayed when you type it. You will not see the usual dots in place of typed characters. Make sure caps lock is off. Type carefully and then press return. You may get a one-time warning to be careful. If you make three failed attempts to enter the password, the test will run anyway, but it will produce less information. In most cases, the difference is not important. If you don't know the password, or if you prefer not to enter it, press the key combination control-C or just press return three times at the password prompt. Again, the script will still run.
    If you're not logged in as an administrator, you won't be prompted for a password. The test will still run. It just won't do anything that requires administrator privileges.
    10. The test may take a few minutes to run, depending on how many files you have and the speed of the computer. A computer that's abnormally slow may take longer to run the test. While it's running, there will be nothing in the Terminal window and no indication of progress. Wait for the line
    [Process completed]
    to appear. If you don't see it within half an hour or so, the test probably won't complete in a reasonable time. In that case, close the Terminal window and report the results. No harm will be done.
    11. When the test is complete, quit Terminal. The results will have been copied to the Clipboard automatically. They are not shown in the Terminal window. Please don't copy anything from there. All you have to do is start a reply to this comment and then paste by pressing command-V again.
    At the top of the results, there will be a line that begins with the words "Start Time." If you don't see that, but instead see a mass of gibberish, you didn't wait for the "Process completed" message to appear in the Terminal window. Please wait for it and try again.
    If any private information, such as your name or email address, appears in the results, anonymize it before posting. Usually that won't be necessary.
    12. When you post the results, you might see the message, "You have included content in your post that is not permitted." It means that the forum software has misidentified something in the post as a violation of the rules. If that happens, please post the test results on Pastebin, then post a link here to the page you created.
    Note: This is a public forum, and others may give you advice based on the results of the test. They speak only for themselves, and I don't necessarily agree with them.
    Copyright © 2014 by Linc Davis. As the sole author of this work, I reserve all rights to it except as provided in the Use Agreement for the Apple Support Communities website ("ASC"). Readers of ASC may copy it for their own personal use. Neither the whole nor any part may be redistributed.

  • What is the best mail account to use with Apple Mail?

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    Hi,
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  • Secure Emailing with Apple Mail/OS X

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    Hello and thanks.
    Yes, at vallnet's suggestion I tried using port 587 and later port 425. No luck. They say that other mail programs are not having difficulties.
    They said they had found some articles on the web about how other small ISPs had also had difficulties with secure connections and Apple Mail. I have not found any such articles yet, and they have not forwarded any links to me.
    Yes, I have been wondering which set of tech support folks was giving me the biggest runaround. You're probably correct, though I suspect both have been less than enthusiastic about trying.
    Yep, we've considered switching email addresses. With several businesses and some personal accounts, this would be a major headache. It seems like a good last resort, but not something that we are happy to do. If we can figure out secure emails, this would be far preferable.
    I do appreciate the feedback. I will keep your suggestion in reserve.
    Many thanks!

  • HT1277 i can receive mail but unable to send mail

    i can receive mail but unable to send mail

    I'm yet another person who upgraded to Maverick OSX. I'm now thinking, "BIG mistake". Mail was working perfectly. Then, last night, Mail stopped sending.
    I've checked everything. Comcast servers are set up correctly. Mail works fine on my ipad, but will not send. It gives me a SMPT error of "Cannot send message using the server comcast.net--authentication rejected" Comcast.net (Offline). I can not get it back online. I've also tried the fixes here, but there is no info.plist by those names in my library!
    Anyone have any other ideas how to get this working again? Apple's OS's have been pretty decently stable in the past. I had no thought that the upgrade would be so problematic. Live and Learn.
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