To reproduce, start on a Bourne shell command line with

cat << EOF > foo.org
* heading heading heading
:properties:
:foo: bar
:end:
EOF

Then start

emacs -Q foo.org

In Emacs continue:

M-x set-variable RET case-fold-search RET nil RET

C-c C-x p foo RET bar RET

For me Org then creates a new property drawer, so the buffer looks like this 
afterwards:

--- snip ---
* heading heading heading
:PROPERTIES:
:foo:      bar
:END:
:properties:
:foo: bar
:end:
--- snip ---

Root cause should be the following snippet in function `org-entry-put':

         (let* ((range (org-get-property-block beg 'force))
                (end (cdr range))
                (case-fold-search t))

When moving `(case-fold-search t)' to before the call of 
`org-get-property-block' things work as expected.

Emacs  : GNU Emacs 28.2 (build 2, x86_64-pc-linux-gnu, X toolkit, cairo version 
1.16.0, Xaw3d scroll bars)
 of 2023-01-18, modified by Debian
Package: Org mode version 9.5.2 (9.5.2 @ 
/usr/share/emacs/site-lisp/elpa/org-9.5.2/)



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