diff --git a/lib/core/test/unit/Network/Wai/Middleware/LoggingSpec.hs b/lib/core/test/unit/Network/Wai/Middleware/LoggingSpec.hs
index 3969456d72e..01fe819065b 100644
--- a/lib/core/test/unit/Network/Wai/Middleware/LoggingSpec.hs
+++ b/lib/core/test/unit/Network/Wai/Middleware/LoggingSpec.hs
@@ -97,6 +97,8 @@ import Test.QuickCheck
     ( Arbitrary (..), choose, property )
 import Test.QuickCheck.Monadic
     ( monadicIO )
+import Test.Utils.Windows
+    ( pendingOnWindows, whenWindows )
 
 import qualified Data.Aeson as Aeson
 import qualified Data.Map.Strict as Map
@@ -195,6 +197,7 @@ spec = describe "Logging Middleware"
             entries <- readTVarIO (logs ctx)
             let index = Map.fromList
                     $ catMaybes [ (loName l,) <$> captureTime l | l <- entries ]
+            pendingOnWindows "Disabled on windows due to race with log flushing"
             Map.size (Map.filter (> (200*ms)) index) `shouldBe` 1
   where
     setup :: IO Context
@@ -267,6 +270,8 @@ postIlled ctx path body = do
 
 expectLogs :: Context -> [(Severity, String)] -> IO ()
 expectLogs ctx expectations = do
+    whenWindows $ threadDelay 1000000 -- let iohk-monitoring flush the logs
+
     entries <- reverse <$> readTVarIO (logs ctx)
 
     when (length entries /= length expectations) $
diff --git a/lib/test-utils/src/Test/Utils/Windows.hs b/lib/test-utils/src/Test/Utils/Windows.hs
index bc5d85997dc..f3eaf8215ce 100644
--- a/lib/test-utils/src/Test/Utils/Windows.hs
+++ b/lib/test-utils/src/Test/Utils/Windows.hs
@@ -8,6 +8,8 @@
 
 module Test.Utils.Windows
     ( skipOnWindows
+    , pendingOnWindows
+    , whenWindows
     ) where
 
 import Prelude
@@ -19,9 +21,15 @@ import Control.Monad
 import System.Info
     ( os )
 import Test.Hspec.Core.Spec
-    ( ResultStatus (..) )
+    ( ResultStatus (..), pendingWith )
 import Test.Hspec.Expectations
     ( Expectation, HasCallStack )
 
 skipOnWindows :: HasCallStack => String -> Expectation
-skipOnWindows _reason = when (os == "mingw32") $ throwIO Success
+skipOnWindows _reason = whenWindows $ throwIO Success
+
+pendingOnWindows :: HasCallStack => String -> Expectation
+pendingOnWindows reason = whenWindows $ pendingWith reason
+
+whenWindows :: IO () -> IO ()
+whenWindows = when (os == "mingw32")