diff --git a/test/src/test/java/jenkins/slaves/restarter/JnlpSlaveRestarterInstallerTest.java b/test/src/test/java/jenkins/slaves/restarter/JnlpSlaveRestarterInstallerTest.java
index 421f00fd5dde..e79ae9590268 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;
@@ -52,12 +54,24 @@ public class JnlpSlaveRestarterInstallerTest {
     @Issue("JENKINS-19055")
     @Test
     public void tcpReconnection() throws Throwable {
+        // TODO Enable when test is reliable on Windows agents of ci.jenkins.io
+        // 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("TODO: Test fails on Windows VM", Functions.isWindows() && System.getenv("CI") != null);
         reconnection(false);
     }
 
     @Issue("JENKINS-66446")
     @Test
     public void webSocketReconnection() throws Throwable {
+        // TODO Enable when test is reliable on Windows agents of ci.jenkins.io
+        // 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("TODO: Test fails on Windows VM", Functions.isWindows() && System.getenv("CI") != null);
         reconnection(true);
     }