OpenSSL: Reuse Key ▶ New CSR ▶ Sign Cert

Copy-ready commands below

I'm hitting the same key-passphrase not-working thing... How did you get past it?
Here are the modified instructions that you should be able to follow.

Step 1 — Use existing key, make a new CSR

$ openssl req -new -key any.key.pem -out new.req.pem

Sample interactive prompts shown by openssl req

You are about to be asked to enter information that will be incorporated
into your certificate request.
What you are about to enter is what is called a Distinguished Name or a DN.
There are quite a few fields but you can leave some blank
For some fields there will be a default value,
If you enter '.', the field will be left blank.
-----
Country Name (2 letter code) [XX]: US
State or Province Name (full name) []: New York
Locality Name (eg, city) [Default City]: Rochester
Organization Name (eg, company) [Default Company Ltd]: Allworx
Organizational Unit Name (eg, section) []:
Common Name (eg, your name or your server's hostname) []: view
Email Address []:

Please enter the following 'extra' attributes
to be sent with your certificate request
A challenge password []:
An optional company name []:

Step 2 — Sign the CSR with the View CA cert

$ openssl ca -in new.req.pem -cert cacert.pem -days 3650 -keyfile cakeysw.pem -out new.cert.pem

Note: 3650 days ≈ 10 years.

Step 3 — Replace the old cert

$ cp new.cert.pem any.cert.pem

Tip: If the CA prompts for a passphrase, ensure you’re using the correct key file (cakeysw.pem) that matches cacert.pem.