Contributor
CJLinst
Posts: 16
Registered: 04-29-2005
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9.9 Messaging Manual Proxy Startup Problem

[ Edited ]
Configuring PGP messaging to use Manual Proxy settings on 127.0.0.1:
(user@example.com used in lieu of my actual config)

PGP->Preferences->Messaging
Discover new accounts: UNCHECKED
Automatically add my email addresses to my key: UNCHECKED
Annotate incoming email: CHECKED
Detail Level: MEDIUM
Add comment to secured messages: UNCHECKED

Encrypt AOL Instand Messages: UNCHECKED

Proxy Options
Email - Manual Proxy using IP: 127.0.0.1
IM - Override port 5190: UNCHECKED

PGP Desktop->PGP Messaging->EXAMPLE.COM
Service properties: EXAMPLE.COM
Description: EXAMPLE.COM
Email Address: user@example.com
Incoming Mail Server: mail.example.com
Outgoing Mail Server: mail.example.com
PGP Universal Server: none
Username: user@example.com
Default Key: Set to my key
Cache this key's passphrase when I log in: UNCHECKED

EXAMPLE.COM Server Settings:

Incoming Mail Server
Server Type: Internet Email (IMAP, POP, SMTP)
Incoming Mail Server: IMAP
Port: Automatic (143)
SSL/TLS: Require STARTTLS
Warn if client attempts SSL/TLS: CHECKED
Redirect local port 10143 to this server

Outgoing Mail Server (SMTP)
Name: mail.example.com
Port: Automatic (25)
SSL/TLS: Require STARTTLS
Warn if email client attempts SSL/TLS: CHECKED
Redirect local port 10025 to this server


NOW FOR THE PROBLEM:

Every time I open PGP Desktop, then nagigate to PGP Messaging->EXAMPLE.COM and click on the server Settings button, I see:

Incoming Mail Server:
Protocol: Automatic (POP/IMAP)

So I change it to:
Protocol: IMAP

Press OK, go back into Settings, and it's reverted to Automatic (POP/IMAP) again. Grr.

Now, PGP Engine appears to be listening on the right port, even if the messaging settings display is confused:

iMac: Preferences user$ netstat -an | grep LISTEN
tcp4 0 0 127.0.0.1.15190 *.* LISTEN
tcp4 0 0 127.0.0.1.10143 *.* LISTEN
tcp4 0 0 127.0.0.1.10110 *.* LISTEN
tcp4 0 0 127.0.0.1.10025 *.* LISTEN
tcp4 0 0 127.0.0.1.631 *.* LISTEN
tcp6 0 0 ::1.631 *.* LISTEN

(Why it's listening on 15190 when I have SPECIFICALLY DISABLED proxy of AIM is a matter for another ticket) (Same goes for 10110 when I'm specifying IMAP.)

Anyway, as my system sits right now, the proxy appears to be working. Now let's do something novel like shutdown and restart...

Okay, we're back. Let's check the PGP Log before we do anything..
cat ~/Library/Logs/PGP/PGPEngine-08-27-2008.log

[ snip the old stuff ]

2008-08-27 12:47:57: Shutting down
2008-08-27 12:48:05: PGP Engine shutting down

**** PGP Universal Log (resuming) ****

2008-08-27 12:49:59: PGP Desktop 9.9.0 (Build 397) starting up
2008-08-27 12:49:59: Initializing PGP Messaging
2008-08-27 12:50:01: Initializing PGP Virtual Disk
2008-08-27 12:50:02: Initializing PGP WDE
2008-08-27 12:50:03: Initializing PGP Tools
2008-08-27 12:50:05: Initializing PGP Messaging
2008-08-27 12:50:05: Ready

Looks great. Let's start Apple Mail.app

Nope. Inbox shows the dreaded Triangle-Bang. Can't connect to the mail server.

iMac: PGP user$ netstat -an | grep LISTEN
tcp4 0 0 127.0.0.1.631 *.* LISTEN
tcp6 0 0 ::1.631 *.* LISTEN

Look at that... PGP Engine isn't listening on 127.0.0.1:10025 or 127.0.0.1:10143. Is PGP Engine running?

iMac: PGP user$ ps -ax | grep PGP
152 ?? 0:01.04 /Library/Application Support/PGP/PGP Engine.app/Contents/MacOS/PGP Engine -psn_0_61455
158 ?? 0:00.20 /Library/Frameworks/PGP.framework/Resources/pgp-agent
161 ?? 0:00.09 /Library/Application Support/PGP/PGP Engine.app/Contents/Resources/PGPdiskEngine
163 ?? 0:00.11 /Library/Application Support/PGP/PGPsyncEngine.app/Contents/MacOS/PGPsyncEngine

Looks like it.

Open PGP Desktop

Check for open ports on 127.0.0.1 - nothing yet.

PGP Messaging->EXAMPLE.COM

Check for listening ports - nothing yet.

Click Settings

Check for listening ports - nothing yet.

Incoming Mail Server
Protocol: Automatic (POP/IMAP)
Leave as is for now and press OK

Check for listening ports:
iMac: PGP user$ netstat -an | grep LISTEN
tcp4 0 0 127.0.0.1.15190 *.* LISTEN
tcp4 0 0 127.0.0.1.10143 *.* LISTEN
tcp4 0 0 127.0.0.1.10110 *.* LISTEN
tcp4 0 0 127.0.0.1.10025 *.* LISTEN
tcp4 0 0 127.0.0.1.631 *.* LISTEN
tcp6 0 0 ::1.631 *.* LISTEN

VIOLA!

Back to Mail.app
Get Mail
Prompts for passphrase.
Mail works again.

This is broken.

Note that this is a FRESH PGP installation, and prior to installing 9.9 I performed all the tasks in the typical "delete all the plists, kill all the processes" instructions.

I opened a ticket.  Support's answer:  Don't use manual proxy mode.

Sorry.  I have to.
Message Edited by CJLinst on 08-27-2008 04:59 PM