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Outlook 2007 hangs while sending large emails (only over HTTPS, not over VPN or while on LAN)

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Last Modified: 2012-06-22
Hey all,

I've got a customer with a very curious problem.  After a reboot of the server, people outside of the office using Outlook 2007 (connecting via Outlook Anywhere/RPC over HTTPS) are unable to send large emails.  

The server is Exchange 2003 SP2 running on an SBS 2003 SP2 R2 box.  The two clients I've tried are both Outlook 2007 SP2.

Here's what I've tested in Outlook:

* Sending emails of any size when connected via VPN works fine
* Sending test emails (under 10k) via RPC over HTTPS works
* Sending larger emails (around 1MB - doesn't matter if it's 1MB of plain text or a 1MB zip attachment) simply hangs for at least 30 minutes until I kill it.  I've turned on Outlook logging and posted the contents below.
* Receiving email seems to be fine via VPN or RPCoHTTPS

Here's an example of the OMPLog.log file:

2010.06.18 17:06:12 <<<< Logging Started (level is LTF_TRACE) >>>>
2010.06.18 17:06:12 HELPER::Initialize called
2010.06.18 17:06:12 Initializing: Finding a Transport
2010.06.18 17:06:12 MAPI XP Call: XPProviderInit in EMSMDB.DLL, hr = 0x00000000
2010.06.18 17:06:12 MAPI XP Call: TransportLogon, hr = 0x8004011d
2010.06.18 17:06:12 MAPI XP Call: Shutdown, hr = 0x00000000
2010.06.18 17:06:12 MAPI XP Call: XPProviderInit in EMSMDB.DLL, hr = 0x00000000
2010.06.18 17:06:14 MAPI Status: (-- -- ---/--- -- ---)
2010.06.18 17:06:14 MAPI XP Call: TransportLogon, hr = 0x00000000
2010.06.18 17:06:14 Initializing: Found a transport, Error code = 0x00000000
2010.06.18 17:06:14 MAPI XP Call: AddressTypes, hr = 0x00000000, cAddrs = 3, cUids = 1
2010.06.18 17:06:14 MAPI XP Call: RegisterOptions, hr = 0x00000000, cOptions = 2
2010.06.18 17:06:14 MAPI Status: (IN -- ---/OUT -- ---)
2010.06.18 17:06:14 MAPI XP Call: TransportNotify(BEGIN_IN|BEGIN_OUT), hr = 0x00000000
2010.06.18 17:06:14 HELPER::Initialize done, Error code = 0x00000000
2010.06.18 17:06:14 HELPER::GetCapabilities called, Error code = 0x00000000
2010.06.18 17:11:26 MAPI Status: (-- -- ---/--- -- ---)
2010.06.18 17:11:28 MAPI Status: (IN -- ---/OUT -- ---)
2010.06.18 17:14:06 MAPI Status: (-- -- ---/--- -- ---)
2010.06.18 17:14:08 MAPI Status: (IN -- ---/OUT -- ---)
2010.06.18 17:19:30 MAPI Status: (-- -- ---/--- -- ---)
2010.06.18 17:19:33 MAPI Status: (IN -- ---/OUT -- ---)
2010.06.18 17:22:05 MAPI Status: (-- -- ---/--- -- ---)
2010.06.18 17:22:08 MAPI Status: (IN -- ---/OUT -- ---)
2010.06.18 17:25:06 MAPI Status: (-- -- ---/--- -- ---)
2010.06.18 17:25:08 MAPI Status: (IN -- ---/OUT -- ---)
2010.06.18 17:28:10 MAPI Status: (-- -- ---/--- -- ---)
2010.06.18 17:28:13 MAPI Status: (IN -- ---/OUT -- ---)
2010.06.18 17:34:40 MAPI Status: (-- -- ---/--- -- ---)
2010.06.18 17:34:43 MAPI Status: (IN -- ---/OUT -- ---)
2010.06.18 17:37:41 MAPI Status: (-- -- ---/--- -- ---)

I've checked in IIS and RPCProxy.dll exists in Web Extensions, with the correct path, and seems to match the size and date of the same file on other SBS 03 customers I support.

Any ideas?
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