Hi,
Looks like there is an issue with Outlook 2013 client. I've noticed that if plain text email is sent with an attachment with SMTP connection then outlook lose the MIME format and sends uuencoded message to exchange server. I believe Outlook/Exchange server still supports the uuencoding so we don't see any problem when the message reaches to recipients but this is creating issues in our outlook add-in. Since our add-in expects that outlook should send MIME message. Outlook shows this peculiar behavior only in case of Plain text email with attachment and SMTP connection. If I repeat the same scenario with same attachment in Outlook 2010, I don't see any issue. Outlook 2010 sends proper MIME message.
I've collected the raw logs of DATA command in case of Outlook 2010 x86 and outlook 2013 x86, which clearly shows the difference. I am trying to send "first.png" attachment in plain test.
*******Data sent by Outlook 2013. MIME hieararchy lost.********
Raw(01): DATA
Raw(01): 354 Start mail input; end with <CRLF>.<CRLF>
Raw(01): From: "rahul sis" <rs@testhulsis.com>
Raw(02): To: <alice@testhulsis.com>
Raw(03): Subject: PT from OL 13
Raw(04): Date: Wed, 29 May 2013 18:35:13 +0530
Raw(05): Message-ID:<004101ce5c6d$28619ec0$7924dc40$@testhulsis.com>
Raw(06): X-Mailer: Microsoft Outlook 15.0
Raw(07): Thread-Index: Ac5canc+mBjJ0ng3QQ6KFoYi1q9khg==
Raw(08): Content-Language: en-us
Raw(09):
Raw(10): PT from OL 13
Raw(11):
Raw(12):
Raw(13): begin 666 first.png
Raw(14): MB5!.1PT*&@H````-24A$4@```!X````>!,```#)'K.1````"7!(67,```L3
Raw(15): M```+$P$`FIP8````)%!,5$7___\`````````````````````````````````
Raw(16): M``````````#')CYE````"W123E,``01-4X2CI-G?^;.E&-8```!H241!5!C3
Raw(17): M8V"@!5#)7#7-"<%E[MZ]>_<.`QB7,7HW"&P5@/)9=T-`)1O#>5OAG"9NJ'\
Raw(18): M'0I@/LMN&' `\]GA_ 0PGQ/.GP#F<\'Y"[#RT=6SH9F';A^Z>]#=B^$?=/^B
Raw(19): <AP=&>%$1```_H7%NQ=]P+@````!)14Y$KD)@@@``
Raw(20): `
Raw(21): end
*******Data sent by Outlook 2010.MIME hieararchy intact********
Raw(01): DATA
Raw(01): 354 Start mail input; end with <CRLF>.<CRLF>
Raw(01): From: "alice" <alice@testhulsis.com>
Raw(02): To: <rs@testhulsis.com>
Raw(03): Subject: PT test from OL 10
Raw(04): Date: Wed, 29 May 2013 18:48:16 +0530
Raw(05): Message-ID:<004301ce5c6e$fafb3c50$f0f1b4f0$@testhulsis.com>
Raw(06): MIME-Version: 1.0
Raw(07): Content-Type: multipart/mixed;
Raw(08): boundary="----=_NextPart_000_0044_01CE5C9D.14B37850"
Raw(09): X-Mailer: Microsoft Outlook 14.0
Raw(10): Thread-Index: Ac5cbuii9deFPUoUQxKGHf6d2p7joA==
Raw(11): Content-Language: en-us
Raw(12):
Raw(13): This is a multipart message in MIME format.
Raw(14):
Raw(15): ------=_NextPart_000_0044_01CE5C9D.14B37850
Raw(16): Content-Type: text/plain;
Raw(17): charset="us-ascii"
Raw(18): Content-Transfer-Encoding: 7bit
Raw(19):
Raw(20): PT test from OL 10
Raw(21):
Raw(22): ------=_NextPart_000_0044_01CE5C9D.14B37850
Raw(23): Content-Type: image/png;
Raw(24): name="first.png"
Raw(25): Content-Transfer-Encoding: base64
Raw(26): Content-Dis
Raw(27): filename="first.png"
Raw(28):
Raw(29):iVBORw0KGgoAAAANSUhEUgAAAB4AAAAeBAMAAADJHrORAAAACXBIWXMAAAsTAAALEwEAmpwYAAAA
Raw(30):JFBMVEX///8AAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAADHJj5lAAAAC3RSTlMAAQRN
Raw(31):U4SjpNnf+bOlGNYAAABoSURBVBjTY2CgBVDJXDXNCcFl7t69e/cOAxiXMXo3CGwVgPJZd0NAAJRv
Raw(32):DeVvhnCZuqH8HQpgPstuGHAA89nh/AQwnxPOnwDmc8H5C7Dy0dWzoZmHbh+6e9Ddi+EfdP+ihwdG
Raw(33): eFERAAA/oXFuxd9wLgAAAABJRU5ErkJggg==
Raw(34):
Raw(35): ------=_NextPart_000_0044_01CE5C9D.14B37850--
Raw(36):
Raw(37): .
I am trying to understand why does outlook 2013 shows this peculiar behavior . Is this a bug or OL2k13 is trying to follow some standard, if yes what standard ?
Looks like there is an issue with Outlook 2013 client. I've noticed that if plain text email is sent with an attachment with SMTP connection then outlook lose the MIME format and sends uuencoded message to exchange server. I believe Outlook/Exchange server still supports the uuencoding so we don't see any problem when the message reaches to recipients but this is creating issues in our outlook add-in. Since our add-in expects that outlook should send MIME message. Outlook shows this peculiar behavior only in case of Plain text email with attachment and SMTP connection. If I repeat the same scenario with same attachment in Outlook 2010, I don't see any issue. Outlook 2010 sends proper MIME message.
I've collected the raw logs of DATA command in case of Outlook 2010 x86 and outlook 2013 x86, which clearly shows the difference. I am trying to send "first.png" attachment in plain test.
*******Data sent by Outlook 2013. MIME hieararchy lost.********
Raw(01): DATA
Raw(01): 354 Start mail input; end with <CRLF>.<CRLF>
Raw(01): From: "rahul sis" <rs@testhulsis.com>
Raw(02): To: <alice@testhulsis.com>
Raw(03): Subject: PT from OL 13
Raw(04): Date: Wed, 29 May 2013 18:35:13 +0530
Raw(05): Message-ID:<004101ce5c6d$28619ec0$7924dc40$@testhulsis.com>
Raw(06): X-Mailer: Microsoft Outlook 15.0
Raw(07): Thread-Index: Ac5canc+mBjJ0ng3QQ6KFoYi1q9khg==
Raw(08): Content-Language: en-us
Raw(09):
Raw(10): PT from OL 13
Raw(11):
Raw(12):
Raw(13): begin 666 first.png
Raw(14): MB5!.1PT*&@H````-24A$4@```!X````>!,```#)'K.1````"7!(67,```L3
Raw(15): M```+$P$`FIP8````)%!,5$7___\`````````````````````````````````
Raw(16): M``````````#')CYE````"W123E,``01-4X2CI-G?^;.E&-8```!H241!5!C3
Raw(17): M8V"@!5#)7#7-"<%E[MZ]>_<.`QB7,7HW"&P5@/)9=T-`)1O#>5OAG"9NJ'\
Raw(18): M'0I@/LMN&' `\]GA_ 0PGQ/.GP#F<\'Y"[#RT=6SH9F';A^Z>]#=B^$?=/^B
Raw(19): <AP=&>%$1```_H7%NQ=]P+@````!)14Y$KD)@@@``
Raw(20): `
Raw(21): end
*******Data sent by Outlook 2010.MIME hieararchy intact********
Raw(01): DATA
Raw(01): 354 Start mail input; end with <CRLF>.<CRLF>
Raw(01): From: "alice" <alice@testhulsis.com>
Raw(02): To: <rs@testhulsis.com>
Raw(03): Subject: PT test from OL 10
Raw(04): Date: Wed, 29 May 2013 18:48:16 +0530
Raw(05): Message-ID:<004301ce5c6e$fafb3c50$f0f1b4f0$@testhulsis.com>
Raw(06): MIME-Version: 1.0
Raw(07): Content-Type: multipart/mixed;
Raw(08): boundary="----=_NextPart_000_0044_01CE5C9D.14B37850"
Raw(09): X-Mailer: Microsoft Outlook 14.0
Raw(10): Thread-Index: Ac5cbuii9deFPUoUQxKGHf6d2p7joA==
Raw(11): Content-Language: en-us
Raw(12):
Raw(13): This is a multipart message in MIME format.
Raw(14):
Raw(15): ------=_NextPart_000_0044_01CE5C9D.14B37850
Raw(16): Content-Type: text/plain;
Raw(17): charset="us-ascii"
Raw(18): Content-Transfer-Encoding: 7bit
Raw(19):
Raw(20): PT test from OL 10
Raw(21):
Raw(22): ------=_NextPart_000_0044_01CE5C9D.14B37850
Raw(23): Content-Type: image/png;
Raw(24): name="first.png"
Raw(25): Content-Transfer-Encoding: base64
Raw(26): Content-Dis
Raw(27): filename="first.png"
Raw(28):
Raw(29):iVBORw0KGgoAAAANSUhEUgAAAB4AAAAeBAMAAADJHrORAAAACXBIWXMAAAsTAAALEwEAmpwYAAAA
Raw(30):JFBMVEX///8AAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAADHJj5lAAAAC3RSTlMAAQRN
Raw(31):U4SjpNnf+bOlGNYAAABoSURBVBjTY2CgBVDJXDXNCcFl7t69e/cOAxiXMXo3CGwVgPJZd0NAAJRv
Raw(32):DeVvhnCZuqH8HQpgPstuGHAA89nh/AQwnxPOnwDmc8H5C7Dy0dWzoZmHbh+6e9Ddi+EfdP+ihwdG
Raw(33): eFERAAA/oXFuxd9wLgAAAABJRU5ErkJggg==
Raw(34):
Raw(35): ------=_NextPart_000_0044_01CE5C9D.14B37850--
Raw(36):
Raw(37): .
I am trying to understand why does outlook 2013 shows this peculiar behavior . Is this a bug or OL2k13 is trying to follow some standard, if yes what standard ?