diff --git a/.github/workflows/build-common.yml b/.github/workflows/build-common.yml
index f023fdb5a24f..cb0b02871546 100644
--- a/.github/workflows/build-common.yml
+++ b/.github/workflows/build-common.yml
@@ -238,9 +238,11 @@ jobs:
 
   test:
     name: test${{ matrix.test-partition }} (${{ matrix.test-java-version }}, ${{ matrix.vm }}, indy ${{ matrix.test-indy }})
-    runs-on: ubuntu-latest
+    runs-on: ${{ matrix.os }}
     strategy:
       matrix:
+        os:
+          - ubuntu-latest
         test-java-version:
           - 8
           - 11
@@ -259,16 +261,45 @@ jobs:
         test-indy:
           - false
           - true
+        include:
+          - os: windows-latest
+            test-java-version: 25
+            vm: hotspot
+            test-partition: 0
+            test-indy: false
+          - os: windows-latest
+            test-java-version: 25
+            vm: hotspot
+            test-partition: 1
+            test-indy: false
+          - os: windows-latest
+            test-java-version: 25
+            vm: hotspot
+            test-partition: 2
+            test-indy: false
+          - os: windows-latest
+            test-java-version: 25
+            vm: hotspot
+            test-partition: 3
+            test-indy: false
         exclude:
           - vm: ${{ inputs.skip-openj9-tests && 'openj9' || '' }}
           - test-java-version: 25-deny-unsafe
             vm: openj9
       fail-fast: false
+    defaults:
+      run:
+        shell: bash
     steps:
+      - name: Support long paths
+        run: git config --system core.longpaths true
+        if: matrix.os == 'windows-latest'
+
       - uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
 
       - name: Free disk space
         run: .github/scripts/gha-free-disk-space.sh
+        if: matrix.os != 'windows-latest'
 
       - id: setup-test-java
         name: Set up JDK ${{ matrix.test-java-version }}-${{ matrix.vm }} for running tests
@@ -300,6 +331,13 @@ jobs:
       - name: Start deadlock detector
         run: .github/scripts/deadlock-detector.sh
 
+      - name: Switch from Windows containers to Linux containers mode
+        if: matrix.os == 'windows-latest'
+        run: |
+          "/c/Program Files/Docker/Docker/DockerCli.exe" -SwitchLinuxEngine
+          # Wait for Docker deamon to restart
+          sleep 30
+
       - name: Setup Gradle
         uses: gradle/actions/setup-gradle@4d9f0ba0025fe599b4ebab900eb7f3a1d93ef4c2 # v5.0.0
         with:
@@ -434,6 +472,7 @@ jobs:
 
       - name: Free disk space
         run: .github/scripts/gha-free-disk-space.sh
+        if: matrix.os != 'windows-latest'
 
       - name: Set up JDK for running Gradle
         uses: actions/setup-java@dded0888837ed1f317902acf8a20df0ad188d165 # v5.0.0
diff --git a/.github/workflows/pr-smoke-test-servlet-images.yml b/.github/workflows/pr-smoke-test-servlet-images.yml
index cb013e29f461..35011513de25 100644
--- a/.github/workflows/pr-smoke-test-servlet-images.yml
+++ b/.github/workflows/pr-smoke-test-servlet-images.yml
@@ -38,6 +38,7 @@ jobs:
 
       - name: Free disk space
         run: .github/scripts/gha-free-disk-space.sh
+        if: matrix.os != 'windows-latest'
 
       - name: Set up JDK for running Gradle
         uses: actions/setup-java@dded0888837ed1f317902acf8a20df0ad188d165 # v5.0.0
diff --git a/instrumentation/async-http-client/async-http-client-1.8/javaagent/src/test/java/io/opentelemetry/javaagent/instrumentation/asynchttpclient/v1_8/AsyncHttpClientTest.java b/instrumentation/async-http-client/async-http-client-1.8/javaagent/src/test/java/io/opentelemetry/javaagent/instrumentation/asynchttpclient/v1_8/AsyncHttpClientTest.java
index 5675dfc9786d..4819b5e7d35a 100644
--- a/instrumentation/async-http-client/async-http-client-1.8/javaagent/src/test/java/io/opentelemetry/javaagent/instrumentation/asynchttpclient/v1_8/AsyncHttpClientTest.java
+++ b/instrumentation/async-http-client/async-http-client-1.8/javaagent/src/test/java/io/opentelemetry/javaagent/instrumentation/asynchttpclient/v1_8/AsyncHttpClientTest.java
@@ -25,6 +25,7 @@
 import java.util.Map;
 import java.util.Set;
 import java.util.concurrent.ExecutionException;
+import org.junit.jupiter.api.condition.OS;
 import org.junit.jupiter.api.extension.RegisterExtension;
 
 class AsyncHttpClientTest extends AbstractHttpClientTest<Request> {
@@ -109,6 +110,12 @@ protected void configure(HttpClientTestOptions.Builder optionsBuilder) {
       optionsBuilder.disableTestReadTimeout();
     }
 
+    // On Windows, non-routable addresses timeout instead of failing fast, causing test timeout
+    // before the HTTP client can create a span, resulting in only the parent span.
+    if (OS.WINDOWS.isCurrentOs()) {
+      optionsBuilder.disableTestRemoteConnection();
+    }
+
     optionsBuilder.setHttpAttributes(
         endpoint -> {
           Set<AttributeKey<?>> attributes =