diff --git a/src/Corrade/Utility/Path.cpp b/src/Corrade/Utility/Path.cpp
index defb657fb..405af4477 100644
--- a/src/Corrade/Utility/Path.cpp
+++ b/src/Corrade/Utility/Path.cpp
@@ -595,9 +595,15 @@ Containers::Optional<Containers::String> homeDirectory() {
     #elif defined(CORRADE_TARGET_WINDOWS) && !defined(CORRADE_TARGET_WINDOWS_RT)
     /** @todo get rid of MAX_PATH */
     wchar_t h[MAX_PATH + 1];
-    /* There doesn't seem to be any possibility how this could fail, so just
-       assert */
-    CORRADE_INTERNAL_ASSERT(SHGetFolderPathW(nullptr, CSIDL_PERSONAL, nullptr, 0, h) == S_OK);
+    /* This could fail for example with E_INVALIDARG for system accounts
+       without a home folder */
+    if(SHGetFolderPathW(nullptr, CSIDL_PERSONAL, nullptr, 0, h) != S_OK) {
+        Error err;
+        err << "Utility::Path::homeDirectory(): can't retrieve CSIDL_PERSONAL:";
+        Utility::Implementation::printWindowsErrorString(err, GetLastError());
+        return {};
+    }
+
     return fromNativeSeparators(Unicode::narrow(h));
 
     /* Other */
@@ -641,11 +647,12 @@ Containers::Optional<Containers::String> configurationDirectory(const Containers
     #elif defined(CORRADE_TARGET_WINDOWS) && !defined(CORRADE_TARGET_WINDOWS_RT)
     /** @todo get rid of MAX_PATH */
     wchar_t path[MAX_PATH];
-    /* There doesn't seem to be any possibility how this could fail, so just
-       assert */
-    CORRADE_INTERNAL_ASSERT(SHGetFolderPathW(nullptr, CSIDL_APPDATA, nullptr, 0, path) == S_OK);
-    if(path[0] == L'\0') {
-        Error{} << "Utility::Path::configurationDirectory(): can't retrieve CSIDL_APPDATA";
+    /* This could fail for example with E_INVALIDARG for system accounts
+       without a home folder */
+    if(SHGetFolderPathW(nullptr, CSIDL_APPDATA, nullptr, 0, path) != S_OK) {
+        Error err;
+        err << "Utility::Path::configurationDirectory(): can't retrieve CSIDL_APPDATA:";
+        Utility::Implementation::printWindowsErrorString(err, GetLastError());
         return {};
     }
     return join(fromNativeSeparators(Unicode::narrow(path)), applicationName);
diff --git a/src/Corrade/Utility/Test/PathTest.cpp b/src/Corrade/Utility/Test/PathTest.cpp
index acfc2ec4b..13ba9199f 100644
--- a/src/Corrade/Utility/Test/PathTest.cpp
+++ b/src/Corrade/Utility/Test/PathTest.cpp
@@ -1530,8 +1530,24 @@ void PathTest::homeDirectory() {
 }
 
 void PathTest::homeDirectoryInvalid() {
-    /* Could be tested by temporarily removing $HOME, but ... ahem */
+    #ifdef CORRADE_TARGET_WINDOWS
+    /* The query fails for system accounts, and system accounts apparently have
+       no access to environment, so checking if %HOMEPATH% is missing:
+       https://serverfault.com/questions/292040/win-service-running-under-localservice-account-cannot-access-environment-variabl */
+    if(std::getenv("HOMEPATH"))
+        CORRADE_SKIP("%HOMEPATH% exists, can't test.");
+
+    std::ostringstream out;
+    Error redirectError{&out};
+    CORRADE_VERIFY(!Path::homeDirectory());
+    CORRADE_COMPARE_AS(out.str(),
+        "Utility::Path::homeDirectory(): can't retrieve CSIDL_PERSONAL: error 666 (",
+        TestSuite::Compare::StringHasPrefix);
+
+    #else
+    /* On Unix could be tested by temporarily removing $HOME, but ... ahem */
     CORRADE_SKIP("Not sure how to test this.");
+    #endif
 }
 
 void PathTest::homeDirectoryUtf8() {
@@ -1601,9 +1617,25 @@ void PathTest::configurationDirectory() {
 }
 
 void PathTest::configurationDirectoryInvalid() {
-    /* Could be tested by temporarily removing $XDG_CONFIG_HOME and $HOME, but
-       ... ahem */
+    #ifdef CORRADE_TARGET_WINDOWS
+    /* The query fails for system accounts, and system accounts apparently have
+       no access to environment, so checking if %HOMEPATH% is missing:
+       https://serverfault.com/questions/292040/win-service-running-under-localservice-account-cannot-access-environment-variabl */
+    if(std::getenv("APPDATA"))
+        CORRADE_SKIP("%APPDATA% exists, can't test.");
+
+    std::ostringstream out;
+    Error redirectError{&out};
+    CORRADE_VERIFY(!Path::configurationDirectory("Corrade"));
+    CORRADE_COMPARE_AS(out.str(),
+        "Utility::Path::configurationDirectory(): can't retrieve CSIDL_APPDATA: error 666 (",
+        TestSuite::Compare::StringHasPrefix);
+
+    #else
+    /* On Unix could be tested by temporarily removing $XDG_CONFIG_HOME and
+       $HOME, but ... ahem */
     CORRADE_SKIP("Not sure how to test this.");
+    #endif
 }
 
 void PathTest::configurationDirectoryUtf8() {