Outlook Plug in Encryption error

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Mar 13th, 2012
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I have the plug-in for email encryption from Outlook installed however after clicking the Encrypt Message button and pressing send, I get the following message: 'An HTTP error occurred during connection to server: unable to establish IP connection'

Forgive me if this is covered in previous topics, I could not find any.

Any insight on this would be appreciated.


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Greg Hopp Tue, 03/13/2012 - 12:01
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Which OS?  Win 7- 64 bit?  Welcome to our world. 

Greg Hopp Tue, 03/13/2012 - 12:08
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Yep, doesn't work.  Even worse, your Outlook may never be the same since you attempted the install.  I was promised this functionality but Cisco has (apparently) failed to deliver.

But I'm not bitter. 

RSteveKadish Tue, 03/20/2012 - 12:41
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This occurs if the plug-in was set to use "desktop encryption" instead of "flag encryption" on install, and you are using CRES as opposed to your own encryption appliance.  Run the plug-in install again from Add/Remove Programs; the second step gives you the choice between desktop and flag encryption.  Change the option to "flag" and you should be all set.

Good luck,

- Steve

Jason Meyer Mon, 08/05/2013 - 09:50
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But it was installed because we need 'Desktop Encryption'.   What is the time frame for fix?

RSteveKadish Mon, 08/05/2013 - 10:38
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Hi Jason,

Sorry, this is an old thread and I'm not really sure what you mean.  What do you need a fix for?  This is normal operation.  When you say you need desktop encryption, what do you mean?  Did you business install your own IronPort encryption appliance?  This is NOT the IronPort Email Security Appliance; it is a seperate box.

- Steve

Jason Meyer Mon, 08/05/2013 - 12:06
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We are using Outlook plug-in 7.3 configured to do Desktop Encryption against CRES.  We also have IEA appliances and we also have ESA appliances and we also have SMA appliances.

The plug-in 7.3 has a bug where it doesn't work with Windows 64 bit and Outlook 32 bit, like the original posts say.  Your fix is to change it to do FLAG encryption.  We need to use DESKTOP encryption for e-mails and because of this bug are not able to on a large number of our workstations, thus your workaround will not help us out.

When will the plug-in be fixed to work with Windows 64 bit and Outlook 32 bit?

When will the plug-in be fixed to support multiple mail profiles of different e-mail addresses? (Defect CSCui42631)


RSteveKadish Mon, 08/05/2013 - 12:17
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Hi Jason,

Gotcha, I understand.  We are using neither Outlook 2010 or Windows 7, but the error referenced in the original post will also occur if you don't have an encryption appliance, install the plugin with the default settings and don't change "desktop encryption" to "flag encryption."  This was the issue we ran into when our help desk installed a bunch of plugins with the wrong settings.

I wasn't aware of the bug, and can't offer you any advice there.  Good luck, and I hope it gets fixed soon!

Jason Meyer Mon, 08/05/2013 - 12:21
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Understood.  I did a TAC support case on it to see what they say.

David Miller Tue, 08/06/2013 - 05:36
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Hi Jason,

My not help but I have installed and run the encryption plug-in under Windows 7 64 bit and Outlook 2010 32 bit and it all seems to work so far.  I installed both email reporting and encryption and then created and emailed an XML profile to update the config to enable desktop encryption, installed that config and desktop encryption then worked. I have tested manage messages, locking an email, and so far no problems.  Details:

WIndows 7 (Home Premium) 64 bit SP1

Outlook 2010 32 bit SP1

Cisco IronPort Email Security Plug-In 7.3.0-102

Java 7 update 7 32 bit

Jason Meyer Mon, 08/12/2013 - 07:48
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My issue turned out to be a proxy issue at the client site.   After connectivity was working the plugin worked as advertised. 


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