Update: We've updated the CA list on our Checkpoint. It' hasn't permitted the traffic from the server to flow but it's something we need to start doing anyway. Not sure how often Checkpoint update the CA list?
I also found out that while the SG's are all R80.30, the SMS is R80.20 (not sure why, I'll be asking). I think I remember reading you can set the CA list to automatically update in R80.30, but not in R80.20. We've set up a process to check for update once a month now anyway.
So the CA change hasn't given us visability of the URL that the client is trying to access through the Checkpoint in SmartConsole or SmartView, but something I have found is the OpenSSL S_client command. If you take the IP address detailed in the blocked traffic and run the OpenSSL S_client on it, if it has connectivity it returns the the certificate details:
>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>
C:\OpenSSL\bin>openssl s_client -connect 40.68.232.16:443
CONNECTED(00000234)
Can't use SSL_get_servername
depth=1 C = US, O = Microsoft Corporation, CN = Microsoft RSA TLS CA 01
verify error:num=20:unable to get local issuer certificate
verify return:1
depth=0 CN = *.blob.core.windows.net
verify return:1
---
Certificate chain
0 s:CN = *.blob.core.windows.net
i:C = US, O = Microsoft Corporation, CN = Microsoft RSA TLS CA 01
1 s:C = US, O = Microsoft Corporation, CN = Microsoft RSA TLS CA 01
i:C = IE, O = Baltimore, OU = CyberTrust, CN = Baltimore CyberTrust Root
---
Server certificate
-----BEGIN CERTIFICATE-----
MIINtDCCC5ygAwIBAgITawADvAdmouS5OGrIsAAAAAO8BzANBgkqhkiG9w0BAQsF
ADBPMQswCQYDVQQ.......
< Truncated to aid visability >
...........x0eVaQiIS1MWC+Jtve6K6Oz43KBXLLTwQ6z
t5zBnzoYOXc=
-----END CERTIFICATE-----
< Truncated to aid visability >
>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>
....and if you copy the text between -----BEGIN CERTIFICATE----- and -----END CERTIFICATE----- (inclusive), copy it in to a text file and run CertUtil -v -dump on it, it will display all the returned certificate's information, even the SAN's detailed in the certificate:
>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>
X509 Certificate:
Version: 3
Serial Number: 6b0003bc0766a2e4b9386ac8b000000003bc07
0000 07 bc 03 00 00 00 b0 c8 6a 38 b9 e4 a2 66 07 bc
0010 03 00 6b
Signature Algorithm:
Algorithm ObjectId: 1.2.840.113549.1.1.11 sha256RSA
Algorithm Parameters:
05 00
Issuer:
CN=Microsoft RSA TLS CA 01
O=Microsoft Corporation
C=US
< Truncated to aid visability >
0003: b0
2.5.29.17: Flags = 0, Length = 631
Subject Alternative Name
DNS Name=*.blob.core.windows.net
DNS Name=*.am5prdstr02a.store.core.windows.net
DNS Name=*.blob.storage.azure.net
DNS Name=*.z1.blob.storage.azure.net
DNS Name=*.z2.blob.storage.azure.net
DNS Name=*.z3.blob.storage.azure.net
DNS Name=*.z4.blob.storage.azure.net
DNS Name=*.z5.blob.storage.azure.net
< Truncated to aid visability >
>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>>
So while not ideal (ideal would be to easily see this info in one of the SMART consoles) we can now at least see a list of potential destination URL's that the client is trying to get to and is being blocked, but I still don't have visability as to why the Checkpoint has blocked the traffic.