diff --git a/.github/workflows/build-and-test-windows.yml b/.github/workflows/build-and-test-windows.yml
index dafbfe3838a8..b4d56ec35f48 100644
--- a/.github/workflows/build-and-test-windows.yml
+++ b/.github/workflows/build-and-test-windows.yml
@@ -45,7 +45,8 @@ jobs:
           - cmd-0
           - cmd-1
           - other
-    runs-on: windows-latest
+        os: [windows-2022, windows-2025]
+    runs-on: ${{ matrix.os }}
     if: ${{ github.actor != 'dependabot[bot]' && (contains(github.event.pull_request.labels.*.name, 'Run Windows') || github.event_name == 'push' || github.event_name == 'merge_group') }}
     env:
       # Limit memory usage via GC environment variables to avoid OOM on GH runners, especially for `cmd/otelcontribcol`,
diff --git a/.github/workflows/e2e-tests-windows.yml b/.github/workflows/e2e-tests-windows.yml
index bcfb4f38d865..69b3f8ac8027 100644
--- a/.github/workflows/e2e-tests-windows.yml
+++ b/.github/workflows/e2e-tests-windows.yml
@@ -32,7 +32,11 @@ jobs:
       - run: echo $(./.github/workflows/scripts/is_changed_file_windows.sh ${{ github.event.pull_request.base.sha }} ${{ github.sha }} )
 
   collector-build:
-    runs-on: windows-latest
+    strategy:
+      fail-fast: false
+      matrix:
+        os: [windows-latest]
+    runs-on: ${{ matrix.os }}
     needs: [windows-file-changed]
     if: ${{ github.actor != 'dependabot[bot]' && ((contains(github.event.pull_request.labels.*.name, 'Run Windows') || github.event_name == 'push' || github.event_name == 'merge_group') || needs.windows-file-changed.outputs.changed == 'true') }}
     steps:
@@ -65,7 +69,11 @@ jobs:
           path: ./bin/*
 
   supervisor-test:
-    runs-on: windows-latest
+    strategy:
+      fail-fast: false
+      matrix:
+        os: [windows-2022, windows-2025]
+    runs-on: ${{ matrix.os }}
     if: ${{ github.actor != 'dependabot[bot]' && (contains(github.event.pull_request.labels.*.name, 'Run Windows') || github.event_name == 'push' || github.event_name == 'merge_group') }}
     needs: [collector-build]
     steps:
@@ -97,7 +105,11 @@ jobs:
           go test -v --tags=e2e
 
   windows-supervisor-service-test:
-    runs-on: windows-latest
+    strategy:
+      fail-fast: false
+      matrix:
+        os: [windows-2022, windows-2025]
+    runs-on: ${{ matrix.os }}
     if: ${{ github.actor != 'dependabot[bot]' && (contains(github.event.pull_request.labels.*.name, 'Run Windows') || github.event_name == 'push' || github.event_name == 'merge_group') }}
     needs: [collector-build]
     steps:
diff --git a/exporter/prometheusremotewriteexporter/exporter_concurrency_test.go b/exporter/prometheusremotewriteexporter/exporter_concurrency_test.go
index 689cbcf7b9fc..bf9fcbd968cc 100644
--- a/exporter/prometheusremotewriteexporter/exporter_concurrency_test.go
+++ b/exporter/prometheusremotewriteexporter/exporter_concurrency_test.go
@@ -8,6 +8,7 @@ import (
 	"io"
 	"net/http"
 	"net/http/httptest"
+	"os"
 	"strconv"
 	"sync"
 	"testing"
@@ -31,6 +32,9 @@ import (
 // Test everything works when there is more than one goroutine calling PushMetrics.
 // Today we only use 1 worker per exporter, but the intention of this test is to future-proof in case it changes.
 func Test_PushMetricsConcurrent(t *testing.T) {
+	if os.Getenv("ImageOs") == "win25" && os.Getenv("GITHUB_ACTIONS") == "true" {
+		t.Skip("Skipping test on Windows 2025 GH runners, see https://github.com/open-telemetry/opentelemetry-collector-contrib/issues/37104")
+	}
 	n := 1000
 	ms := make([]pmetric.Metrics, n)
 	testIDKey := "test_id"
@@ -52,6 +56,10 @@ func Test_PushMetricsConcurrent(t *testing.T) {
 			t.Fatal(err)
 		}
 		assert.NotNil(t, body)
+		if len(body) == 0 {
+			// No content, nothing to do. The request is just checking that the server is up.
+			return
+		}
 		// Receives the http requests and unzip, unmarshalls, and extracts TimeSeries
 		assert.Equal(t, "0.1.0", r.Header.Get("X-Prometheus-Remote-Write-Version"))
 		assert.Equal(t, "snappy", r.Header.Get("Content-Encoding"))
@@ -124,6 +132,13 @@ func Test_PushMetricsConcurrent(t *testing.T) {
 		require.NoError(t, prwe.Shutdown(ctx))
 	}()
 
+	// Ensure that the test server is up before making the requests
+	assert.EventuallyWithT(t, func(c *assert.CollectT) {
+		resp, checkRequestErr := http.Get(server.URL)
+		require.NoError(c, checkRequestErr)
+		assert.NoError(c, resp.Body.Close())
+	}, 5*time.Second, 100*time.Millisecond)
+
 	var wg sync.WaitGroup
 	wg.Add(n)
 	for _, m := range ms {