Certificate not generating when spaces in filepath

[cdavid138]

Hi there,

I've been battling with this for a couple of days and looking for some assistance.

It seems to be since moving my user folder onto a different internal HD, i'm unable to generate SSLs for sites getting the error:

nginx: [emerg] cannot load certificate "/Volumes/Storage HD/Users/david/.config/valet/Certificates/healthkit.test.crt": BIO_new_file() failed (SSL: error:02001002:system library:fopen:No such file or directory:fopen('/Volumes/Storage HD/Users/david/.config/valet/Certificates/healthkit.test.crt','r') error:2006D080:BIO routines:BIO_new_file:no such file)
nginx: configuration file /usr/local/etc/nginx/nginx.conf test failed

I've read through
#807
#329

Unfortunatley those errors have not helped.

Running
Mac OS: 10.15.1
Valet: 2.5.4

~ brew services list
Name      Status  User  Plist
dnsmasq   started root  /Library/LaunchDaemons/homebrew.mxcl.dnsmasq.plist
mysql@5.7 started david /Volumes/Storage HD/Users/david/Library/LaunchAgents/homebrew.mxcl.mysql@5.7.plist
nginx     started root  /Library/LaunchDaemons/homebrew.mxcl.nginx.plist
php@7.3   started root  /Library/LaunchDaemons/homebrew.mxcl.php@7.3.plist

Certificates not successfully being generated but no errors when using valet secure

~ ls -ltr ~/.config/valet/Certificates
total 24
-rwxrwxrwx  1 david  staff  1675  3 Dec 09:45 healthkit.test.key
-rwxrwxrwx  1 david  staff  1074  3 Dec 09:45 healthkit.test.csr
-rwxrwxrwx  1 david  staff   744  3 Dec 09:45 healthkit.test.conf

Completely fresh install as of yesterday evening, all help appreciated thanks!

[drbyte]

seems to be since moving my user folder onto a different internal HD

No such file... fopen(
'/Volumes/Storage HD/Users/david/.config/valet/Certificates/healthkit.test.crt'

First guess: I'm wondering if maybe it's not liking the space in your volume name Storage HD when trying to write the .crt file. It looks like the other 3 related files are created fine though.

As such, I'm curious whether if you wrap the single remaining %s in double-quotes like "%s" in these 3 lines
of your ~/.composer/vendor/laravel/valet/cli/Valet/Site.php file
(and then re-run valet secure healthkit)
... maybe that'll fix it for you?

valet/cli/Valet/Site.php

Line 374 in 3d877ef

'openssl x509 -req -sha256 -days 730 -CA "%s" -CAkey "%s" %s -in "%s" -out "%s" -extensions v3_req -extfile "%s"',

valet/cli/Valet/Site.php

Line 381 in 3d877ef

'openssl x509 -req -sha256 -days 730 -CA "%s" -CAkey "%s" %s -in "%s" -out "%s" -extensions v3_req -extfile "%s"',

valet/cli/Valet/Site.php

Line 436 in 3d877ef

'sudo security add-trusted-cert -d -r trustAsRoot -k /Library/Keychains/System.keychain %s', $crtPath

[cdavid138]

Thanks for the help!

No such luck with that solution im afraid. Same result, three files generated, no .crt.

Also note that the output of valet links doesn't show the SSL enabled for that site, but I assume that's because its checking for the existance of a .crt file.

Password:
+-----------+-----+-----------------------+----------------------------------------------------------+
| Site      | SSL | URL                   | Path                                                     |
+-----------+-----+-----------------------+----------------------------------------------------------+
| healthkit |     | http://healthkit.test | /Volumes/Storage HD/Users/david/Documents/Work/healthkit |
+-----------+-----+-----------------------+----------------------------------------------------------+

[drbyte]

Also note that the output of valet links doesn't show the SSL enabled for that site, but I assume that's because its checking for the existance of a .crt file.

Yes, that's exactly right.

[drbyte]

It's probably too drastic to explore renaming that Storage HD volume to have no space, right?

[drbyte]

Next best step would be manually running the various openssl commands that Valet performs, to see whether any errors are coming up, and dealing with whatever they mean.

In that same Site.php file around line 373 you have this section of code. Try changing it as follows, and the attempt valet secure again:

        $result = $this->cli->runAsUser(sprintf(
            'openssl x509 -req -sha256 -days 730 -CA "%s" -CAkey "%s" %s -in "%s" -out "%s" -extensions v3_req -extfile "%s"',
            $caPemPath, $caKeyPath, $caSrlParam, $csrPath, $crtPath, $confPath
-        ));
+        ),
+            function ($exitCode, $outputMessage) {
+                throw new DomainException("errors: [$exitCode: $outputMessage].");
+            }
+        );

[cdavid138]

Perfect thanks, will give that a go now.

I did try a rename of the HD, to just Storage, but same result.

Will proceed with testing these commands now.

[cdavid138]

Getting somewhere...

  errors: [1: unknown option -CAserial /Volumes/Storage HD/Users/david/.config/valet/CA/LaravelValetCASelfSigned.srl -CAcreateserial
  usage: x509 args

Possible this is an openssl error?

[drbyte]

That feels like space issue causing parameters to be misinterpreted

[cdavid138]

So i think that was caused by adding the quotes around the remaining %s values, as it resulted in the added params for $caSrlParam being contained within the quotes, ie:

" -CAserial ..."

So i've now modified it to add the quotes around the filepath a few lines above as follows:

$caSrlParam = '-CAserial "' . $caSrlPath . '"';

That results in the command the code is running as follows

openssl x509 -req -sha256 -days 730 -CA "/Volumes/Storage HD/Users/david/.config/valet/CA/LaravelValetCASelfSigned.pem" -CAkey "/Volumes/Storage HD/Users/david/.config/valet/CA/LaravelValetCASelfSigned.key" -CAserial "/Volumes/Storage HD/Users/david/.config/valet/CA/LaravelValetCASelfSigned.srl" -CAcreateserial -in "/Volumes/Storage HD/Users/david/.config/valet/Certificates/healthkit.test.csr" -out "/Volumes/Storage HD/Users/david/.config/valet/Certificates/healthkit.test.crt" -extensions v3_req -extfile "/Volumes/Storage HD/Users/david/.config/valet/Certificates/healthkit.test.conf"

Which does execute correctly when run directly on the command line, but still getting the error when its run as part of the valet secure script.

[drbyte]

Good work.

So, if it works fine on its own, are we sure your Valet is correctly generating the same command?

[cdavid138]

Okay changing the following line actually sorted it once I removed the quotes around the %s that we added.

$caSrlParam = '-CAserial "' . $caSrlPath . '"';

However now getting NET::ERR_CERT_INVALID, so i'm assuming we're now failing to add this to the keychain somewhere?

[drbyte]

However now getting NET::ERR_CERT_INVALID, so i'm assuming we're now failing to add this to the keychain somewhere?

Ya, probably in trustCertificate() line 437-ish

[drbyte]

I imagine 437 and 424 probably both need the added quotation-marks.
(424 more on a fresh install where you haven't already generated the CA Cert yet)

[cdavid138]

Yup!

Perfect we're all sorted, thanks for the help!

I'll tidy this up and submit as a PR later in the week, I don't imagine it would have a detrimental effect on anyone that doesn't have this issue, and would certainly help anyone that does have a space in their path somewhere!

Thanks again for the help, really appreciate it!

[drbyte]

Cool. Glad it was relatively painless in the end!

Yes, a PR would be welcome.

You may already know this, but I'll say it for completeness: Be sure to mention "Closes #862" in the Commit Message or the PR text, so it properly refers to and closes this issue.

Maybe also mention in the PR title something about spaces in volume name. Actually, might be good to also update the title(subject) of this Issue mentioning that too.