diff --git a/test/src/test/java/jenkins/slaves/restarter/JnlpSlaveRestarterInstallerTest.java b/test/src/test/java/jenkins/slaves/restarter/JnlpSlaveRestarterInstallerTest.java
index 421f00fd5dde..a13c94a5d241 100644
--- a/test/src/test/java/jenkins/slaves/restarter/JnlpSlaveRestarterInstallerTest.java
+++ b/test/src/test/java/jenkins/slaves/restarter/JnlpSlaveRestarterInstallerTest.java
@@ -25,7 +25,9 @@
 package jenkins.slaves.restarter;
 
 import static org.junit.Assert.assertEquals;
+import static org.junit.Assume.assumeFalse;
 
+import hudson.Functions;
 import hudson.model.Slave;
 import hudson.slaves.DumbSlave;
 import java.util.concurrent.atomic.AtomicBoolean;
@@ -49,15 +51,31 @@ public class JnlpSlaveRestarterInstallerTest {
     @Rule
     public LoggerRule logging = new LoggerRule().record(JnlpSlaveRestarterInstaller.class, Level.FINE).capture(10);
 
+    private static final String JENKINS_URL = System.getenv("JENKINS_URL") != null
+            ? System.getenv("JENKINS_URL")
+            : "http://localhost:8080/";
+
     @Issue("JENKINS-19055")
     @Test
     public void tcpReconnection() throws Throwable {
+        // TODO Enable when test is reliable on Windows
+        // When builds switched from ACI containers to virtual machines, this test consistently failed
+        // When the test is run on local Windows computers, it passes
+        // Disable the test on ci.jenkins.io and friends when running Windows
+        // Do not disable for Windows developers generally
+        assumeFalse(Functions.isWindows() && JENKINS_URL.contains("ci.jenkins.io"));
         reconnection(false);
     }
 
     @Issue("JENKINS-66446")
     @Test
     public void webSocketReconnection() throws Throwable {
+        // TODO Enable when test is reliable on Windows
+        // When builds switched from ACI containers to virtual machines, this test consistently failed
+        // When the test is run on local Windows computers, it passes
+        // Disable the test on ci.jenkins.io and friends when running Windows
+        // Do not disable for Windows developers generally
+        assumeFalse(Functions.isWindows() && JENKINS_URL.contains("ci.jenkins.io"));
         reconnection(true);
     }