diff --git a/pkgs/applications/emulators/wine/sources.nix b/pkgs/applications/emulators/wine/sources.nix
index 698b386300dba..c395bc91b81ee 100644
--- a/pkgs/applications/emulators/wine/sources.nix
+++ b/pkgs/applications/emulators/wine/sources.nix
@@ -92,6 +92,14 @@ let
     })
   ];
 
+  patches-add-dll-accept-device-paths-wine-older-than-11_1 = [
+    (pkgs.fetchpatch {
+      name = "add-dll-accept-device-paths";
+      url = "https://gitlab.winehq.org/wine/wine/-/commit/401910ae25a11032f2da7baa1666d71e8bca2496.patch";
+      hash = "sha256-2726u9/vhhx39Tq7vOw24hslmeyZZEbxRRqe7JMFvCU";
+    })
+  ];
+
   inherit (pkgs) writeShellScript;
 in
 rec {
@@ -123,7 +131,8 @@ rec {
     patches = [
       # Also look for root certificates at $NIX_SSL_CERT_FILE
       ./cert-path.patch
-    ];
+    ]
+    ++ patches-add-dll-accept-device-paths-wine-older-than-11_1;
 
     updateScript = writeShellScript "update-wine-stable" ''
       ${updateScriptPreamble}
diff --git a/pkgs/development/haskell-modules/configuration-windows.nix b/pkgs/development/haskell-modules/configuration-windows.nix
index 3dd93aa5c17f8..2072fb9fe1bb4 100644
--- a/pkgs/development/haskell-modules/configuration-windows.nix
+++ b/pkgs/development/haskell-modules/configuration-windows.nix
@@ -8,11 +8,23 @@ with haskellLib;
 
 (self: super: {
   # cabal2nix doesn't properly add dependencies conditional on os(windows)
-  network =
-    if pkgs.stdenv.hostPlatform.isWindows then
-      addBuildDepends [ self.temporary ] super.network
-    else
-      super.network;
+  network = lib.pipe super.network [
+    (addBuildDepends [ self.temporary ])
+
+    # https://github.com/haskell/network/pull/605
+    (appendPatch (fetchpatch {
+      name = "dont-frag-wine.patch";
+      url = "https://github.com/haskell/network/commit/ecd94408696117d34d4c13031c30d18033504827.patch";
+      sha256 = "sha256-8LtAkBmgMMMIW6gPYDVuwYck/4fcOf08Hp2zLmsRW2w=";
+    }))
+  ];
+
+  # Workaround for
+  #   Mingw-w64 runtime failure:
+  #   32 bit pseudo relocation at 00000001400EB99E out of range, targeting 00006FFFFFEB8170, yielding the value 00006FFEBFDCC7CE.
+  # Root cause seems to be undefined references to libffi as shown by linking errors if we instead use "-Wl,--disable-auto-import"
+  # See https://github.com/rust-lang/rust/issues/132226#issuecomment-2445100058
+  iserv-proxy = appendConfigureFlag "--ghc-option=-optl=-Wl,--disable-runtime-pseudo-reloc" super.iserv-proxy;
 
   # Avoids a cycle by disabling use of the external interpreter for the packages that are dependencies of iserv-proxy.
   # See configuration-nix.nix, where iserv-proxy and network are handled.
diff --git a/pkgs/development/haskell-modules/generic-builder.nix b/pkgs/development/haskell-modules/generic-builder.nix
index 955c0a4381848..4e3617e7efab8 100644
--- a/pkgs/development/haskell-modules/generic-builder.nix
+++ b/pkgs/development/haskell-modules/generic-builder.nix
@@ -13,6 +13,7 @@
   haskellLib,
   iserv-proxy,
   nodejs,
+  windows,
   writeShellScriptBin,
 }:
 
@@ -36,11 +37,14 @@ let
               enableExecutableProfiling = enableProfiling;
             };
             buildProxy = lib.getExe' iserv-proxy.build "iserv-proxy";
-            hostProxy = lib.getExe' (overrides iserv-proxy.host) "iserv-proxy-interpreter";
+            hostProxy = lib.getExe' (overrides iserv-proxy.host) (
+              "iserv-proxy-interpreter" + stdenv.hostPlatform.extensions.executable
+            );
           in
           buildPackages.writeShellScriptBin ("iserv-wrapper" + lib.optionalString enableProfiling "-prof") ''
             set -euo pipefail
             PORT=$((5000 + $RANDOM % 5000))
+            ${lib.optionalString stdenv.hostPlatform.isWindows "export WINEDEBUG=-all WINEPREFIX=$TMP"}
             (>&2 echo "---> Starting interpreter on port $PORT")
             ${emulator} ${hostProxy} tmp $PORT &
             RISERV_PID="$!"
@@ -355,11 +359,17 @@ let
   ++ optional (allPkgconfigDepends != [ ]) "--with-pkg-config=${pkg-config.targetPrefix}pkg-config"
 
   ++ optionals enableExternalInterpreter (
-    map (opt: "--ghc-option=${opt}") [
-      "-fexternal-interpreter"
-      "-pgmi"
-      crossSupport.iservWrapper
-    ]
+    map (opt: "--ghc-option=${opt}") (
+      [
+        "-fexternal-interpreter"
+        "-pgmi"
+        crossSupport.iservWrapper
+      ]
+      ++ lib.optionals stdenv.hostPlatform.isWindows [
+        "-L${windows.pthreads}/bin"
+        "-L${windows.pthreads}/lib"
+      ]
+    )
   );
 
   makeGhcOptions = opts: lib.concatStringsSep " " (map (opt: "--ghc-option=${opt}") opts);