Apache is failing to start with error: Failed to configure encrypted (?) private key after configuring SSL

• Unable to setup Windchill and Apache to use HTTPS
• Using certificates of type *.pfx supplied by end customer
• Extract key and server Certificate using openssl from *.pfx
• After CPS update unable to start Apache
• Key file gets encrypted using openssl
• Apache error.log reads: 

[ssl:emerg] [pid 7484:tid 532] AH02577: Init: SSLPassPhraseDialog builtin is not supported on Win32 (key file E:/ptc/Windchill_11.2/HTTPServer/conf/windchillrfs.crt)
 [ssl:emerg] [pid 7484:tid 532] AH02311: Fatal error initialising mod_ssl, exiting. See E:/ptc/Windchill_11.2/HTTPServer/logs/error.log for more information
[ssl:emerg] [pid 7484:tid 532] AH02564: Failed to configure encrypted (?) private key <host>:443:1, check E:/ptc/Windchill_11.2/HTTPServer/conf/windchillrfs.crt
[ssl:emerg] [pid 7484:tid 532] SSL Library Error: error:0D0680A8:asn1 encoding routines:asn1_check_tlen:wrong tag

[Tue Oct 03 16:16:39.681166 2023] [ssl:emerg] [pid 6240:tid 336] AH02577: Init: SSLPassPhraseDialog builtin is not supported on Win32 (key file C:/ptc/Windchill_12.1/HTTPServer/conf/server.key)
[Tue Oct 03 16:16:39.681166 2023] [ssl:emerg] [pid 6240:tid 336] AH02311: Fatal error initialising mod_ssl, exiting. See C:/ptc/Windchill_12.1/HTTPServer/logs/error.log for more information
[Tue Oct 03 16:16:39.681166 2023] [ssl:emerg] [pid 6240:tid 336] AH02564: Failed to configure encrypted (?) private key 10.171.44.8:443:0, check C:/ptc/Windchill_12.1/HTTPServer/conf/server.key
[Tue Oct 03 16:16:39.681166 2023] [ssl:emerg] [pid 6240:tid 336] SSL Library Error: error:0D0680A8:asn1 encoding routines:asn1_check_tlen:wrong tag
[Tue Oct 03 16:16:39.681166 2023] [ssl:emerg] [pid 6240:tid 336] SSL Library Error: error:0D07803A:asn1 encoding routines:asn1_item_embed_d2i:nested asn1 error (Type=PKCS8_PRIV_KEY_INFO)
[Tue Oct 03 16:16:39.681166 2023] [ssl:emerg] [pid 6240:tid 336] SSL Library Error: error:0D0680A8:asn1 encoding routines:asn1_check_tlen:wrong tag
[Tue Oct 03 16:16:39.681166 2023] [ssl:emerg] [pid 6240:tid 336] SSL Library Error: error:0D08303A:asn1 encoding routines:asn1_template_noexp_d2i:nested asn1 error
[Tue Oct 03 16:16:39.681166 2023] [ssl:emerg] [pid 6240:tid 336] SSL Library Error: error:0D0680A8:asn1 encoding routines:asn1_check_tlen:wrong tag
[Tue Oct 03 16:16:39.681166 2023] [ssl:emerg] [pid 6240:tid 336] SSL Library Error: error:0D07803A:asn1 encoding routines:asn1_item_embed_d2i:nested asn1 error (Type=RSAPrivateKey)
[Tue Oct 03 16:16:39.681166 2023] [ssl:emerg] [pid 6240:tid 336] SSL Library Error: error:04093004:rsa routines:old_rsa_priv_decode:RSA lib
[Tue Oct 03 16:16:39.681166 2023] [ssl:emerg] [pid 6240:tid 336] SSL Library Error: error:0D0680A8:asn1 encoding routines:asn1_check_tlen:wrong tag
[Tue Oct 03 16:16:39.681166 2023] [ssl:emerg] [pid 6240:tid 336] SSL Library Error: error:0D07803A:asn1 encoding routines:asn1_item_embed_d2i:nested asn1 error (Type=PKCS8_PRIV_KEY_INFO)
AH00016: Configuration Failed