Openssl on freebsd certificate use in windows

H

Hoser

Hello All,

I have a problem when I try to use an openssl certificate created on freebsd copied over to windows.
The certificate is unusable and creashes my email server when used.
If I create another certificate using openssl on windows everything works file.
I also noticed that the certificate on freebsd is much smaller on freebsd.
To copy the certificate from freebsd I use ssh.

Any help would be appreciated, Thanks
 
What commands do you use on each machine?

What files are you using? Not sure what you mean about file sizes - use md5 or something to check the file has copied across to Windows.

What does “crashes“ mean? What program? Any error messages? Is there a way to turn on debug logging?

More of a OpenSSL question or the email program you are using rather than a FreeBSD question I suspect.
 
I highly doubt a certificate on some client will crash a mailserver...

But why would you want to use a self-signed certificate for a mail server anyways?
Nothing else (i.e. other mailservers) can/will talk to that server over TLS, so use a proper certificate e.g. from let's encrypt, then you also don't have to import it manually on the client/MUA.
There are a bunch of acme clients in ports; I use/recommend security/acme.sh.
 
Unfortunately, PEM is still the most common format for certificates nowadays. Line breaks are significant, but not standardized in that format. What's likely happening is the Freebsd file uses UNIX-like line endings (LF) and the Windows machine is expecting Windows line endings (CRLF). This is a very common problem. Top hit from a Google search:
superuser.com

Convert Unix line endings to Windows

I recently moved back to Windows from Linux. I have some files with CRLFs, some with LFs and some that are mixed. Is there a utility that will help me find all my Unix-touched files and convert the...
superuser.com superuser.com
 
Thank you for your helpful suggestions SKO and Jose, I'll try both your suggestions.

Best Regards
 
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