diff --git a/modules/rostests/apitests/user32/PrivateExtractIcons.c b/modules/rostests/apitests/user32/PrivateExtractIcons.c
index 85edab85a16..aff24a195ed 100644
--- a/modules/rostests/apitests/user32/PrivateExtractIcons.c
+++ b/modules/rostests/apitests/user32/PrivateExtractIcons.c
@@ -27,8 +27,9 @@ BOOL ResourceToFile(INT i, PCWSTR FileName)
 
     if (FileExists(FileName))
     {
-        skip("'%S' already exists. Exiting now\n", FileName);
-        return FALSE;
+        /* We should only be using %temp% paths, so deleting here should be OK */
+        printf("Deleting '%S' that already exists.\n", FileName);
+        DeleteFileW(FileName);
     }
 
     hRes = FindResourceW(NULL, MAKEINTRESOURCEW(i), MAKEINTRESOURCEW(RT_RCDATA));
@@ -90,6 +91,12 @@ static struct
 
     /* Icon group file containing one PNG icon and one normal icon */
     {L"%temp%\\ROS.ico", 1, 1, TRUE},
+
+    /* Executable file with bad 'Icon Group' but good 'Icons'.
+     * Windows explorer shows the program's icon correctly in WinXP/Win2K3
+     * but Windows 7 shows only a default icon. This is analogous
+     * to EXE's generated by older Watcom C/C++ versions. */
+    {L"%temp%\\cpimg2e.exe", 1, 1, TRUE},
 };
 
 static struct
@@ -100,6 +107,7 @@ static struct
 {
     {L"%temp%\\ROS.ico", IDR_ICONS_PNG},
     {L"%temp%\\sysicon.ico", IDR_ICONS_NORMAL},
+    {L"%temp%\\cpimg2e.exe", IDR_EXE_NORMAL}
 };
 
 START_TEST(PrivateExtractIcons)
diff --git a/modules/rostests/apitests/user32/cpimg2e.exe b/modules/rostests/apitests/user32/cpimg2e.exe
new file mode 100644
index 00000000000..db9d844a615
Binary files /dev/null and b/modules/rostests/apitests/user32/cpimg2e.exe differ
diff --git a/modules/rostests/apitests/user32/resource.h b/modules/rostests/apitests/user32/resource.h
index ac91b1b51be..33972fde705 100644
--- a/modules/rostests/apitests/user32/resource.h
+++ b/modules/rostests/apitests/user32/resource.h
@@ -3,3 +3,4 @@
 
 #define IDR_ICONS_PNG 2000
 #define IDR_ICONS_NORMAL 2001
+#define IDR_EXE_NORMAL 2002
diff --git a/modules/rostests/apitests/user32/user32_apitest.rc b/modules/rostests/apitests/user32/user32_apitest.rc
index 370c3aaa721..155390fc217 100644
--- a/modules/rostests/apitests/user32/user32_apitest.rc
+++ b/modules/rostests/apitests/user32/user32_apitest.rc
@@ -10,6 +10,7 @@ TESTCURSOR CURSOR "test.cur"
 
 IDR_ICONS_PNG RCDATA "ROS.ico"
 IDR_ICONS_NORMAL RCDATA "sysicon.ico"
+IDR_EXE_NORMAL RCDATA "cpimg2e.exe"
 
 TESTDIALOG DIALOG 0,0, 200,200
 CLASS "TestDialogClass"