diff --git a/mesonbuild/backend/backends.py b/mesonbuild/backend/backends.py
index 44c3caeca..e56d18d8d 100644
--- a/mesonbuild/backend/backends.py
+++ b/mesonbuild/backend/backends.py
@@ -617,8 +617,12 @@ class Backend:
                 exe_wrapper = self.environment.cross_info.config['binaries'].get('exe_wrapper', None)
             else:
                 exe_wrapper = None
-            if mesonlib.is_windows() or mesonlib.is_cygwin():
-                extra_paths = self.determine_windows_extra_paths(exe, [])
+            if mesonlib.for_windows(is_cross, self.environment) or \
+               mesonlib.for_cygwin(is_cross, self.environment):
+                extra_bdeps = []
+                if isinstance(exe, build.CustomTarget):
+                    extra_bdeps = exe.get_transitive_build_target_deps()
+                extra_paths = self.determine_windows_extra_paths(exe, extra_bdeps)
             else:
                 extra_paths = []
             cmd_args = []
diff --git a/mesonbuild/backend/ninjabackend.py b/mesonbuild/backend/ninjabackend.py
index b32733885..6082c8502 100644
--- a/mesonbuild/backend/ninjabackend.py
+++ b/mesonbuild/backend/ninjabackend.py
@@ -530,7 +530,11 @@ int dummy;
         # the project, we need to set PATH so the DLLs are found. We use
         # a serialized executable wrapper for that and check if the
         # CustomTarget command needs extra paths first.
-        if mesonlib.is_windows() or mesonlib.is_cygwin():
+        is_cross = self.environment.is_cross_build() and \
+            self.environment.cross_info.need_cross_compiler() and \
+            self.environment.cross_info.need_exe_wrapper()
+        if mesonlib.for_windows(is_cross, self.environment) or \
+           mesonlib.for_cygwin(is_cross, self.environment):
             extra_bdeps = target.get_transitive_build_target_deps()
             extra_paths = self.determine_windows_extra_paths(target.command[0], extra_bdeps)
             if extra_paths:
diff --git a/mesonbuild/mtest.py b/mesonbuild/mtest.py
index 9dd4cbddb..2a052d6a8 100644
--- a/mesonbuild/mtest.py
+++ b/mesonbuild/mtest.py
@@ -231,11 +231,27 @@ class SingleTestRunner:
                 self.test.timeout = None
             return self._run_cmd(wrap + cmd + self.test.cmd_args + self.options.test_args)
 
+    @staticmethod
+    def _substring_in_list(substr, strlist):
+        for s in strlist:
+            if substr in s:
+                return True
+        return False
+
     def _run_cmd(self, cmd):
         starttime = time.time()
 
         if len(self.test.extra_paths) > 0:
             self.env['PATH'] = os.pathsep.join(self.test.extra_paths + ['']) + self.env['PATH']
+            if self._substring_in_list('wine', cmd):
+                wine_paths = ['Z:' + p for p in self.test.extra_paths]
+                wine_path = ';'.join(wine_paths)
+                # Don't accidentally end with an `;` because that will add the
+                # current directory and might cause unexpected behaviour
+                if 'WINEPATH' in self.env:
+                    self.env['WINEPATH'] = wine_path + ';' + self.env['WINEPATH']
+                else:
+                    self.env['WINEPATH'] = wine_path
 
         # If MALLOC_PERTURB_ is not set, or if it is set to an empty value,
         # (i.e., the test or the environment don't explicitly set it), set
diff --git a/mesonbuild/scripts/meson_exe.py b/mesonbuild/scripts/meson_exe.py
index 46d501faa..a70accac6 100644
--- a/mesonbuild/scripts/meson_exe.py
+++ b/mesonbuild/scripts/meson_exe.py
@@ -57,6 +57,15 @@ def run_exe(exe):
     if len(exe.extra_paths) > 0:
         child_env['PATH'] = (os.pathsep.join(exe.extra_paths + ['']) +
                              child_env['PATH'])
+        if exe.exe_runner and 'wine' in exe.exe_runner:
+            wine_paths = ['Z:' + p for p in exe.extra_paths]
+            wine_path = ';'.join(wine_paths)
+            # Don't accidentally end with an `;` because that will add the
+            # current directory and might cause unexpected behaviour
+            if 'WINEPATH' in child_env:
+                child_env['WINEPATH'] = wine_path + ';' + child_env['WINEPATH']
+            else:
+                child_env['WINEPATH'] = wine_path
 
     p = subprocess.Popen(cmd + exe.cmd_args, env=child_env, cwd=exe.workdir,
                          close_fds=False,