Applications that use the Cryptography API cannot validate an X.509 certificate in Windows Server 2003

Cause

========

One such case is Windows Server 2003 and the SHA-2 family of algorithms. Windows Server 2003does not understand SHA-2 family of algorithms.

https://support.microsoft.com/en-us/help/938397/applications-that-use-the-cryptography-api-cannot-validate-an-x.509-certificate-in-windows-server-2003

SSL/TLS the Alert Codes

Alert Code	Alert Message	Description
0	close_notify	Notifies the recipient that the sender will not send any more messages on this connection.
10	unexpected_message	Received an inappropriate message This alert should never be observed in communication between proper implementations. This message is always fatal.
20	bad_record_mac	Received a record with an incorrect MAC. This message is always fatal.
21	decryption_failed	Decryption of a TLSCiphertext record is decrypted in an invalid way: either it was not an even multiple of the block length or its padding values, when checked, were not correct. This message is always fatal.
22	record_overflow	Received a TLSCiphertext record which had a length more than 2^14+2048 bytes, or a record decrypted to a TLSCompressed record with more than 2^14+1024 bytes. This message is always fatal.
30	decompression_failure	Received improper input, such as data that would expand to excessive length, from the decompression function. This message is always fatal.
40	handshake_failure	Indicates that the sender was unable to negotiate an acceptable set of security parameters given the options available. This is a fatal error.
42	bad_certificate	There is a problem with the certificate, for example, a certificate is corrupt, or a certificate contains signatures that cannot be verified.
43	unsupported_certificate	Received an unsupported certificate type.
44	certificate_revoked	Received a certificate that was revoked by its signer.
45	certificate_expired	Received a certificate has expired or is not currently valid.
46	certificate_unknown	An unspecified issue took place while processing the certificate that made it unacceptable.
47	illegal_parameter	Violated security parameters, such as a field in the handshake was out of range or inconsistent with other fields. This is always fatal.
48	unknown_ca	Received a valid certificate chain or partial chain, but the certificate was not accepted because the CA certificate could not be located or could not be matched with a known, trusted CA. This message is always fatal.
49	access_denied	Received a valid certificate, but when access control was applied, the sender did not proceed with negotiation. This message is always fatal.
50	decode_error	A message could not be decoded because some field was out of the specified range or the length of the message was incorrect. This message is always fatal.
51	decrypt_error	Failed handshake cryptographic operation, including being unable to correctly verify a signature, decrypt a key exchange, or validate a finished message.
60	export_restriction	Detected a negotiation that was not in compliance with export restrictions; for example, attempting to transfer a 1024 bit ephemeral RSA key for the RSA_EXPORT handshake method. This message is always fatal.
70	protocol_version	The protocol version the client attempted to negotiate is recognized, but not supported. For example, old protocol versions might be avoided for security reasons. This message is always fatal.
71	insufficient_security	Failed negotiation specifically because the server requires ciphers more secure than those supported by the client. Returned instead of handshake_failure. This message is always fatal.
80	internal_error	An internal error unrelated to the peer or the correctness of the protocol makes it impossible to continue, such as a memory allocation failure. The error is not related to protocol. This message is always fatal.
90	user_cancelled	Cancelled handshake for a reason that is unrelated to a protocol failure. If the user cancels an operation after the handshake is complete, just closing the connection by sending a close_notify is more appropriate. This alert should be followed by a close_notify. This message is generally a warning.
100	no_renegotiation	Sent by the client in response to a hello request or sent by the server in response to a client hello after initial handshaking. Either of these would normally lead to renegotiation; when that is not appropriate, the recipient should respond with this alert; at that point, the original requester can decide whether to proceed with the connection. One case where this would be appropriate would be where a server has spawned a process to satisfy a request; the process might receive security parameters (key length, authentication, and so on) at start-up and it might be difficult to communicate changes to these parameters after that point. This message is always a warning.
255	unsupported_extension

Upgrade Certification Authority to SHA256

A common question in the field is about upgrading a certification authority running on Windows Server 2003 to use Crypto Next Generation (CNG) to support SHA256. CNG was introduced in Windows Server 2008 and higher operating systems, as a result,
an upgrade to the operating system is required. After upgrading the certification authority’s operating system, you will need to run
the following commands from an elevated command line window:

certutil -setreg ca\csp\CNGHashAlgorithm SHA256
net stop certsvc
net start certsvc

Make sure you are  using a Key Storage Provider that supports SHA256 – for example the Microsoft Key Storage Provider - and then renewing the certification authority’s certificate.

If this proves to be too complicated, then you can simply issue certificates to clients using SHA256 even if the entire certification authority’s chain is signed with SHA1 certificates. The applications consuming the SHA256 certificates have to support the SHA256 signature on any given certificate in the chain.

Getting event ID 64 with the event source CertificateServicesClient-AutoEnrollment

Event Source:  CertificateServicesClient-AutoEnrollment

Event ID:  64

Description:  Certificate for local system with Thumbprint [CERTIFICATE THUMBPRINT] is about to expire or already has expired.

Cause

========

It appears that the CA that issued the Server certificates had been removed from the network and these expired certificates where left in the local computer certificate store.

Resolution

===========

1.  Logon to the Server.

2.  Type in:  MMC

3.  Click on File menu option and select Add/Remove Snap-in.

4.  Select Certificate and click the Add button.

5.  Select Computer account, then Next.

6.  Click on Local Computer and click on the Finish button.

7.  Click the OK button.

8.  Once the certificates MMC is click on:  Certificates (Local Computer)\Personal

9.  Delete all the expired certificates.