diff --git a/lib/std/debug/SelfInfo/Windows.zig b/lib/std/debug/SelfInfo/Windows.zig
index ccf7263461..710b13c122 100644
--- a/lib/std/debug/SelfInfo/Windows.zig
+++ b/lib/std/debug/SelfInfo/Windows.zig
@@ -368,7 +368,7 @@ const Module = struct {
                 /// iteration, e.g. because they only wanted the topmost call.
                 inline_sites: std.ArrayList(*align(1) const std.pdb.InlineSiteSym),
             },
-            dwarf: struct { addr: usize },
+            dwarf: struct { addr: u64 },
             none: void,
 
             fn init(di: *DebugInfo, vaddr: usize) Error!Symbols {
diff --git a/test/tests.zig b/test/tests.zig
index 97f99cffed..a4c0bbcf6e 100644
--- a/test/tests.zig
+++ b/test/tests.zig
@@ -2016,10 +2016,24 @@ fn nativeAndCompatible32bit(b: *std.Build, skip_non_native: bool) []const std.Bu
         },
         else => return only_native,
     };
-    return b.graph.arena.dupe(std.Build.ResolvedTarget, &.{
-        b.graph.host,
-        b.resolveTargetQuery(.{ .cpu_arch = arch32, .os_tag = host.os.tag }),
-    }) catch @panic("OOM");
+    var targets = std.ArrayList(std.Build.ResolvedTarget).initCapacity(b.graph.arena, 2)
+        catch @panic("OOM");
+    targets.appendAssumeCapacity(b.graph.host);
+    targets.appendAssumeCapacity(b.resolveTargetQuery(.{
+        .cpu_arch = arch32,
+        .os_tag = host.os.tag,
+    }));
+    if (b.enable_wine and b.graph.host.result.os.tag != .windows) {
+        targets.append(b.graph.arena, b.resolveTargetQuery(.{
+            .cpu_arch = host.cpu.arch,
+            .os_tag = .windows,
+        })) catch @panic("OOM");
+        targets.append(b.graph.arena, b.resolveTargetQuery(.{
+            .cpu_arch = arch32,
+            .os_tag = .windows,
+        })) catch @panic("OOM");
+    }
+    return targets.toOwnedSlice(b.graph.arena) catch @panic("OOM");
 }
 
 pub fn addStackTraceTests(