Cannot create SSL certificate request file

Question

I am trying to create a ssl sertificate for my apache virtual hosts for my local development using this guide. But all my attempts are in vain because of the error.

STEPS I DO

ssh-keygen -f server.key Two files was created (server.key and server.key.pub) Their content is:

server.key

server.key.pub

ssh-rsa AAAAB3NzaC1yc2EAAAADAQABAAABgQDB5oFG9xeqy1Q8XOfepXk1soRSpQ5XbpO1bABUwuQmmoSG8tt/2r2730MichhS6pUbVPrU+wg2FGqBsXYZmzvZsMGwi7cJjZU/kEjzXbnWinM3fV0bTPOcge+59WSO5FvPe85235dkP1ZGwLIET1n6ni/Xg9L5DXlLmSf6YOhP5I7CiQEFEi1TQ6pvqqDuPZ6MCKg+FAQi3gu6GGBDwIyo+xLiI01q71rgjd/GT1LUOhSScZDEFgYw9kkaFh9z0T0Y3q7Hw7zpDQCjg+Tc9ZtO3gf5ulAD/cqD55ktBM0gWJroYx9g8JTUVgYZDgJz2kGDeSukiW71ETW1ThtFSvtEY7FligNWjWvWggmEeVhs6OhLaNEc/2l30O8No6OwzaFIZHT6Co7BDNGJpBY5zyku51qFFZ0sGLgRv7wsdzcpJs/Gr7fBrI3bQGQnQ4ZfHlEWyMMqIN1+59vWADpejM2hz+7HsjWaLgR361PnrSKowqN9DAcRbY6z6NmOAEN3Ac8= alex@MacBook-Air-alex.local

Encodings of this files:

Then I am trying to create request file: sudo openssl req -new -key server.key -out request.csr and on this step I see this:

unable to load Private Key 8672677548:error:09FFF06C:PEM routines:CRYPTO_internal:no start line:/System/Volumes/Data/SWE/macOS/BuildRoots/e90674e518/Library/Caches/com.apple.xbs/Sources/libressl/libressl-56.60.2/libressl-2.8/crypto/pem/pem_lib.c:684:Expecting: ANY PRIVATE KEY

I have tried to change encoding but still encounter same error, but maybe I'm doing something wrong. Most things I found in the internet are outdated, are any proven solutions exist?

You need to convert the keys into pem format http://sysmic.org/dotclear/index.php?post/2010/03/24/Convert-keys-betweens-GnuPG%2C-OpenSsh-and-OpenSSL — kofemann, Jul 04 '21 at 06:47
@kofemann by command `openssl rsa -in server.key -out server.pem`? If so - it returns same error — Alexey, Jul 04 '21 at 06:50
The guide you use is wrong. You cannot directly use a key generated by ssh-keygen to create a CSR. SSH key format is not suitable here. Create your key using `openssl genrsa -out server.key` or similar. Follow other guides like [this](https://www.ssl.com/how-to/manually-generate-a-certificate-signing-request-csr-using-openssl/) instead. — Steffen Ullrich, Jul 04 '21 at 07:27
Alternatively you can convert the SSH key to PEM using ssh-keygen - see [Openssh Private Key to RSA Private Key](https://stackoverflow.com/questions/54994641/openssh-private-key-to-rsa-private-key). — Steffen Ullrich, Jul 04 '21 at 08:38
@SteffenUllrich Thank you. You can write this as an answer, because it worked for me — Alexey, Jul 05 '21 at 15:35

Cannot create SSL certificate request file

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