.htaccess strange Redirect behaviour - .htaccess

Question

I have following .htaccess (domain names have been changed and file shortened):
RewriteEngine On
RewriteCond %{HTTPS} !=on
RewriteRule ^.*$ https://%{SERVER_NAME}%{REQUEST_URI} [R=302,L]
Redirect 302 / https://www.destination.com/software/pwa
Redirect 302 /cases https://www.destination.com/cases
Redirect 302 /cases/digitaal-meldpunt-voor https://www.destination.com/cases/ontwikkeling
When I visit https://www.example.com, I am redirected properly to https://www.destination.com/software/pwa. But when I visit https://www.example.com/cases, I am being redirected to https://www.destination.com/software/pwacases.
Looks like the first rule is interfering with the others and I have no clue why, Google says that this should be working properly.
If I rewrite the .htaccess to:
RewriteEngine On
RewriteCond %{HTTPS} !=on
RewriteRule ^.*$ https://%{SERVER_NAME}%{REQUEST_URI} [R=302,L]
RewriteRule ^(|/)$ https://www.destination.com/software/pwa [R=302,L]
RewriteRule ^cases(|/)$ https://www.destination.com/cases [R=302,L]
Both redirects are working properly. Why doesn't the first .htaccess work as intended?

Answer 1

Redirect 302 / https://www.destination.com/software/pwa
Redirect 302 /cases https://www.destination.com/cases
Redirect 302 /cases/digitaal-meldpunt-voor https://www.destination.com/cases/ontwikkeling
As noted in comments, the mod_alias Redirect directive uses simple prefix-matching, and everything after the match is appended to the end of the target URL. So, the first redirect above matches everything and everything after the initial slash is appended to the end of the target URL - which is what you are seeing.
To resolve this you can reorder the Redirect directives so the most specific is first.
Or, you could use a mod_alias RedirectMatch instead which matches against a regex (like the mod_rewrite RewriteRule), rather than simple prefix-matching.
For example:
RedirectMatch 302 ^/$ https://www.destination.com/software/pwa
RedirectMatch 302 ^/cases$ https://www.destination.com/cases
RedirectMatch 302 ^/cases/digitaal-meldpunt-voor$ https://www.destination.com/cases/ontwikkeling
Which matches only the URLs /, /cases or /cases/digitaal-meldpunt-voor exactly.
Note that in your RewriteRule (mod_rewrite) directives you have also allowed for an optional trailing slash? The Redirect directives would also have allowed for an optional trailing slash because they are prefix-matching.
It is the prefix-matching nature of the Redirect directive that allows you to easily mass-redirect everything from one domain to another whilst maintaining the URL-path:
Redirect / https://newdomain.example/