diff --git a/highlighters/main/test-data/option-path_dirs.zsh b/highlighters/main/test-data/option-path_dirs.zsh
index 1f3002a..0300c7e 100644
--- a/highlighters/main/test-data/option-path_dirs.zsh
+++ b/highlighters/main/test-data/option-path_dirs.zsh
@@ -27,15 +27,18 @@
 # vim: ft=zsh sw=2 ts=2 et
 # -------------------------------------------------------------------------------------------------
 
-## setup
-setopt PATH_DIRS
-mkdir -p foo/bar
-touch foo/bar/testing-issue-228
-chmod  +x foo/bar/testing-issue-228
-path+=( "$PWD"/foo )
+if [[ $OSTYPE == msys ]]; then
+  skip_test='Cannot chmod +x in msys2'
+else
+  setopt PATH_DIRS
+  mkdir -p foo/bar
+  touch foo/bar/testing-issue-228
+  chmod  +x foo/bar/testing-issue-228
+  path+=( "$PWD"/foo )
 
-BUFFER='bar/testing-issue-228'
+  BUFFER='bar/testing-issue-228'
 
-expected_region_highlight=(
-  "1 21 command" # bar/testing-issue-228
-)
+  expected_region_highlight=(
+    "1 21 command" # bar/testing-issue-228
+  )
+fi
diff --git a/highlighters/main/test-data/path-broken-symlink.zsh b/highlighters/main/test-data/path-broken-symlink.zsh
index 84c7d59..c99f872 100644
--- a/highlighters/main/test-data/path-broken-symlink.zsh
+++ b/highlighters/main/test-data/path-broken-symlink.zsh
@@ -27,10 +27,14 @@
 # vim: ft=zsh sw=2 ts=2 et
 # -------------------------------------------------------------------------------------------------
 
-ln -s /nonexistent broken-symlink
-BUFFER=': broken-symlink'
-CURSOR=5 # to make path_prefix ineligible
+if [[ $OSTYPE == msys ]]; then
+  skip_test='Cannot create symlinks in msys2'
+else
+  ln -s /nonexistent broken-symlink
+  BUFFER=': broken-symlink'
+  CURSOR=5 # to make path_prefix ineligible
 
-expected_region_highlight=(
-  "3 16 path" # broken-symlink
-)
+  expected_region_highlight=(
+    "3 16 path" # broken-symlink
+  )
+fi