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Could Not Contact Server Error When Connected to Sophos as Update Source

We have a few clients that connect to update from Sophos as their primary (and sole) location. The system is connected to the Internet and the connection to Sophos is not being blocked.

When doing so, the update fails with "Could Not Conact Server". This only started a few months ago, here is a snippet of the log when I try to perform a manual update:

Trace(2013-Jul-30 09:00:20): ALUpdate started: -ManualUpdate  -NoGUI -RootPath "C:\Program Files (x86)\Sophos\AutoUpdate"
Trace(2013-Jul-30 09:00:20): Product subscription is disabled: iProductData.{390DCDC2-10A9-4ef3-B8D8-0CA7F0E7EB92} action value is:0
Trace(2013-Jul-30 09:00:20): Product iProductData.{390DCDC2-10A9-4ef3-B8D8-0CA7F0E7EB92} has not been added.
Trace(2013-Jul-30 09:00:20): Product subscription is disabled: iProductData.{D752FAB9-5883-4b36-8740-61565B6BAD29} action value is:0
Trace(2013-Jul-30 09:00:20): Product iProductData.{D752FAB9-5883-4b36-8740-61565B6BAD29} has not been added.
Trace(2013-Jul-30 09:00:20): Product iProductData.{E17FE03B-0501-4aaa-BC69-0129D965F311} has been added.
Trace(2013-Jul-30 09:00:20): Product iProductData.{E17FE03B-0501-4aaa-BC69-0129D965F311} is  available from Sophos.
Trace(2013-Jul-30 09:00:20): Product iProductData.{E17FE03B-0501-4aaa-BC69-0129D965F311} is not  the Spam Rules package.
Trace(2013-Jul-30 09:00:20): Product subscription is disabled: iProductData.{7998C326-2CA5-4830-B7D2-B792D2460975} action value is:0
Trace(2013-Jul-30 09:00:20): Product iProductData.{7998C326-2CA5-4830-B7D2-B792D2460975} has not been added.
Trace(2013-Jul-30 09:00:20): Product iProductData.{3B758ED7-87C1-4e89-BDE1-F49DFF1249F6} has not been added.
Trace(2013-Jul-30 09:00:20): Product iProductData.{B5E7E2A7-3B64-437D-801F-21CC9D67CC6D} has been added.
Trace(2013-Jul-30 09:00:20): Product iProductData.{B5E7E2A7-3B64-437D-801F-21CC9D67CC6D} is  available from Sophos.
Trace(2013-Jul-30 09:00:20): Product iProductData.{B5E7E2A7-3B64-437D-801F-21CC9D67CC6D} is  the Spam Rules package.
Trace(2013-Jul-30 09:00:20): Computer is a not possible cluster
Trace(2013-Jul-30 09:00:20): PureMessageDetector::AreSpamRulesRequired - Could not open registry on Software\Sophos\MMEx\Config\Global
Trace(2013-Jul-30 09:00:20): ConfigurationImpl, considering PMSR 2.6: PureMessage not installed, PMSR package will not be updated without a subscription
Trace(2013-Jul-30 09:00:20): Considering subscribed products.
Trace(2013-Jul-30 09:00:20): Considering product {9BF40A4E-23AE-48be-9974-5A1F261DBEE8}
Trace(2013-Jul-30 09:00:20): Product {9BF40A4E-23AE-48be-9974-5A1F261DBEE8} is not already subscribed.
Trace(2013-Jul-30 09:00:20): Product {9BF40A4E-23AE-48be-9974-5A1F261DBEE8} was added to the list.
Trace(2013-Jul-30 09:00:20): Could not read registry entry containing Sophos address - using hardcoded value.
Trace(2013-Jul-30 09:00:20): Could not read registry entry containing Sophos address - using hardcoded value.
Trace(2013-Jul-30 09:00:20): GenerateCustomerID: complete
Trace(2013-Jul-30 09:00:20): Computer is a not possible cluster
Trace(2013-Jul-30 09:00:20): PureMessageDetector::AreSpamRulesRequired - Could not open registry on Software\Sophos\MMEx\Config\Global
Trace(2013-Jul-30 09:00:20): IPCBase::IPCBase: Initialising shared memory A32951C539924a12B3C8F2FDA5A268E4
Trace(2013-Jul-30 09:00:20): IPCSender::ProcessSend started
Trace(2013-Jul-30 09:00:20): IPCSender::ProcessSend: No messages in queue, starting to wait
Trace(2013-Jul-30 09:00:20): RMSMessageHandler: ALUpdateStart
Trace(2013-Jul-30 09:00:20): IPCSender::Write: Writing message: <?xml version="1.0" encoding="utf-8" ?><Config type="RMSStartUpdate" />
Trace(2013-Jul-30 09:00:20): IPCSender::ProcessSend: Send message: <?xml version="1.0" encoding="utf-8" ?><Config type="RMSStartUpdate" />
Trace(2013-Jul-30 09:00:20): IPCSender::ProcessSend: No messages in queue, starting to wait
Trace(2013-Jul-30 09:00:20): ALUpdate(AutoUpdate.Started):
Trace(2013-Jul-30 09:00:20): UpdateCoordinator::UpdateNow: Entering
Trace(2013-Jul-30 09:00:20): PopulateCache: Entering
Trace(2013-Jul-30 09:00:20): UpdateCoordinator::UpdateNow: About to Sync list of products
Trace(2013-Jul-30 09:00:20): UpdateLocationFacade::SyncProduct: Last Update Mechanism = Unknown
Trace(2013-Jul-30 09:00:20): TrySyncProduct<class AutoUpdate::SDDSUpdateLocation>, Started:
Trace(2013-Jul-30 09:00:20): TrySyncProduct<class AutoUpdate::SDDSUpdateLocation>, creating update location
Trace(2013-Jul-30 09:00:20): Path to decode files to: C:\Windows\TEMP\sophos_autoupdate1.dir\1375189220
Trace(2013-Jul-30 09:00:20): Using top level catalogue sdds.esc_10
Trace(2013-Jul-30 09:00:20): SDDSUpdateLocation, constructor start
Trace(2013-Jul-30 09:00:20): locConfig.m_server = Sophos
Trace(2013-Jul-30 09:00:20): Calling check on source.m_address.m_path = Sophos
Trace(2013-Jul-30 09:00:20): Calling package_source_init
Trace(2013-Jul-30 09:00:20): Creating package source to represent parent
Trace(2013-Jul-30 09:00:20): Create package source to represent local cache
Trace(2013-Jul-30 09:00:20): SDDSUpdateLocation::Constructor finished
Trace(2013-Jul-30 09:00:20): TrySyncProduct, Calling BeginSync
Trace(2013-Jul-30 09:00:21): Opened catalogue!
Trace(2013-Jul-30 09:00:21): Attempting to synchronise load balancing and redirection files
Trace(2013-Jul-30 09:00:21): Failed to synchronise load balancing and redirection files: Bad certificate chain!
Trace(2013-Jul-30 09:00:21): TrySyncProduct<class AutoUpdate::SDDSUpdateLocation>, Calling SyncProduct with {E17FE03B-0501-4aaa-BC69-0129D965F311}
Trace(2013-Jul-30 09:00:21): SDDSUpdate(SyncProduct.Start): SAVXP, Sophos
Trace(2013-Jul-30 09:00:21): SDDSUpdateLocation caught exception from download: Bad certificate chain!
Trace(2013-Jul-30 09:00:21): SDDSUpdate(SDDSDownloadFailed): SAVXP, Sophos
Trace(2013-Jul-30 09:00:22): TrySyncProduct<class AutoUpdate::SDDSUpdateLocation>, SyncProduct returned - 0
Trace(2013-Jul-30 09:00:22): TrySyncProduct<class AutoUpdate::SDDSUpdateLocation>, Ended - 0
Trace(2013-Jul-30 09:00:22): UpdateLocationFacade::SyncProduct: Last Update Mechanism = Unknown
Trace(2013-Jul-30 09:00:22): TrySyncProduct<class AutoUpdate::SDDSUpdateLocation>, Started:
Trace(2013-Jul-30 09:00:22): TrySyncProduct<class AutoUpdate::SDDSUpdateLocation>, creating update location
Trace(2013-Jul-30 09:00:22): Path to decode files to: C:\Windows\TEMP\sophos_autoupdate1.dir\1375189222
Trace(2013-Jul-30 09:00:22): Using top level catalogue sdds.esc_10
Trace(2013-Jul-30 09:00:22): SDDSUpdateLocation, constructor start
Trace(2013-Jul-30 09:00:22): locConfig.m_server = Sophos
Trace(2013-Jul-30 09:00:22): Calling check on source.m_address.m_path = Sophos
Trace(2013-Jul-30 09:00:22): Calling package_source_init
Trace(2013-Jul-30 09:00:22): Creating package source to represent parent
Trace(2013-Jul-30 09:00:22): Create package source to represent local cache
Trace(2013-Jul-30 09:00:22): SDDSUpdateLocation::Constructor finished
Trace(2013-Jul-30 09:00:22): TrySyncProduct, Calling BeginSync
Trace(2013-Jul-30 09:00:22): Opened catalogue!
Trace(2013-Jul-30 09:00:22): Attempting to synchronise load balancing and redirection files
Trace(2013-Jul-30 09:00:22): Failed to synchronise load balancing and redirection files: Bad certificate chain!
Trace(2013-Jul-30 09:00:22): TrySyncProduct<class AutoUpdate::SDDSUpdateLocation>, Calling SyncProduct with {9BF40A4E-23AE-48be-9974-5A1F261DBEE8}
Trace(2013-Jul-30 09:00:22): SDDSUpdate(SyncProduct.Start): Sophos AutoUpdate, Sophos
Trace(2013-Jul-30 09:00:22): SDDSUpdateLocation caught exception from download: Bad certificate chain!
Trace(2013-Jul-30 09:00:22): SDDSUpdate(SDDSDownloadFailed): Sophos AutoUpdate, Sophos
Trace(2013-Jul-30 09:00:23): TrySyncProduct<class AutoUpdate::SDDSUpdateLocation>, SyncProduct returned - 0
Trace(2013-Jul-30 09:00:23): TrySyncProduct<class AutoUpdate::SDDSUpdateLocation>, Ended - 0
Trace(2013-Jul-30 09:00:23): ALUpdate():
Trace(2013-Jul-30 09:00:23): ALUpdate(DownloadEnded):
Trace(2013-Jul-30 09:00:23): UpdateCoordinator::UpdateNow: About to Action list of products
Trace(2013-Jul-30 09:00:24): RMSMessageHandler: ALUpdateEnd
Trace(2013-Jul-30 09:00:24): Sending message: <?xml version="1.0" encoding="utf-8" ?><Config type="RMSEndUpdate"><ErrorMessage><ID></ID><StringID>113</StringID><Sender>ALUpdate</Sender></ErrorMessage><ReadableMessage>ERROR:   Could not find a source for updated packages</ReadableMessage></Config>
Trace(2013-Jul-30 09:00:24): IPCSender::Write: Writing message: <?xml version="1.0" encoding="utf-8" ?><Config type="RMSEndUpdate"><ErrorMessage><ID></ID><StringID>113</StringID><Sender>ALUpdate</Sender></ErrorMessage><ReadableMessage>ERROR:   Could not find a source for updated packages</ReadableMessage></Config>
Trace(2013-Jul-30 09:00:24): IPCSender::ProcessSend: Listener not ready starting to wait
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