How to determine what TLS ciphers are being used in OSX, Outlook 2011

hackingms officeopensslSecurityssl

I just limited all my SSL ciphers to TLS 1.X and TLS1_RSA_AES and my up-to-date OSX machine is no longer able to connect to the server via Outlook 2011.

I can use Safari to connect to the same host, so this is probably an app-specific issue.

How do I, in OSX, figure out what TLS cipher and protocol is being used to connect to a given host?

This is necessary to remove security risks with SSL3, BEAST, CRIME, POODLE, and other security risks.

Ideally I will remove all ciphers locally that use RC4 and other risky protocol negotiations.

Best Answer

As you already remarked, the use of ciphers and protocol version is application specific. The easiest way to check which ciphers and protocol version is currently used by an application is to either use wireshark to sniff and look at the TLS handshake (ClientHello contains the cipher offers) or to use some server which displays these information from the SSL handshake, like SSLLabs.

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MacBook – Outlook 2011, Where are the mails stored

According to Microsoft's support site:

Outlook stores only the indices in the Database (with a capital “D”) file and stores the data records as a series of files nested within folders. The Database file and its folders are located here:

~/Documents/Microsoft User Data/Office 2011 Identities/Main Identity/Database
~/Documents/Microsoft User Data/Office 2011 Identities/Main Identity/Data Records

IPhone – How to sync MobileMe with Outlook 2011

Outlook, like Entourage before it, isn't setup to support MobileMe natively as an account that it will sync more than Mail with. I understand you eventually want to get data to your iPhone, but Apple's central MobileMe service just can't talk to Outlook as you're hoping, which I will now attempt to explain:

In the past, syncing other types of data than mail was accomplished by setting up MobileMe in each of the corresponding apple apps(iCal, Address Book) and then enabling SyncServices in Entourage to have it push and pull updates to the data. With Outlok 2011's release, only contacts were supported via Address Book, and mishaps were reported when Calendars were eventually turned on: http://www.pcworld.com/article/224461/microsoft_blames_apple_for_outlook_2011_sync_snafu.html

The moral of the story is Microsoft has shown little excellence in the area of email clients besides the ones on its platform(Outlook for Windows) talking to its mail service(Exchange). Apple will have the best clients for its service, even if it is spread across multiple apps(unless you choose to use the web interface for everything).

More background on what was available, and one report on using 2011 with sync services: http://www.macworld.com/article/155727/2010/11/outlook2011faq.html and http://www.scrubly.com/blog/index.php/2011/01/how-to-sync-outlook-2011-for-mac-with-mac-address-book/

Best Answer

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MacBook – Outlook 2011, Where are the mails stored

IPhone – How to sync MobileMe with Outlook 2011

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