diff --git a/quarkus/tests/integration/src/test/java/org/keycloak/it/cli/dist/QuarkusPropertiesDistTest.java b/quarkus/tests/integration/src/test/java/org/keycloak/it/cli/dist/QuarkusPropertiesDistTest.java
index 6db22c54691..5ecc227a1a7 100644
--- a/quarkus/tests/integration/src/test/java/org/keycloak/it/cli/dist/QuarkusPropertiesDistTest.java
+++ b/quarkus/tests/integration/src/test/java/org/keycloak/it/cli/dist/QuarkusPropertiesDistTest.java
@@ -22,9 +22,11 @@ import io.restassured.RestAssured;
 import org.junit.jupiter.api.Disabled;
 import org.junit.jupiter.api.MethodOrderer.OrderAnnotation;
 import org.junit.jupiter.api.Order;
+import org.junit.jupiter.api.Tag;
 import org.junit.jupiter.api.Test;
 import org.junit.jupiter.api.TestMethodOrder;
 import org.junit.jupiter.api.condition.DisabledOnOs;
+import org.junit.jupiter.api.condition.EnabledOnOs;
 import org.junit.jupiter.api.condition.OS;
 import org.keycloak.it.junit5.extension.BeforeStartDistribution;
 import org.keycloak.it.junit5.extension.CLIResult;
@@ -44,6 +46,7 @@ import static org.keycloak.quarkus.runtime.cli.command.AbstractStartCommand.OPTI
 
 @DistributionTest(reInstall = DistributionTest.ReInstall.NEVER)
 @RawDistOnly(reason = "Containers are immutable")
+@Tag(DistributionTest.WIN)
 @TestMethodOrder(OrderAnnotation.class)
 public class QuarkusPropertiesDistTest {
 
@@ -68,19 +71,38 @@ public class QuarkusPropertiesDistTest {
 
     @Test
     @Launch({"-Dquarkus.log.handler.console.\"console-2\".enable=false", "start", "--http-enabled=true", "--hostname-strict=false"})
+    @DisabledOnOs(value = { OS.WINDOWS })
     @Order(3)
     void testIgnoreQuarkusSystemPropertiesAtStart(CLIResult cliResult) {
         cliResult.assertMessage("Keycloak is the best");
     }
 
+    @Test
+    @Launch({"-Dquarkus.log.handler.console.\\\"console-2\\\".enable=false", "start", "--http-enabled=true", "--hostname-strict=false"})
+    @EnabledOnOs(value = { OS.WINDOWS }, disabledReason = "Different handling of quotes within arguments on Windows")
+    @Order(3)
+    void testIgnoreQuarkusSystemPropertiesAtStartWin(CLIResult cliResult) {
+        cliResult.assertMessage("Keycloak is the best");
+    }
+
     @Test
     @Launch({"-Dquarkus.log.handler.console.\"console-2\".enable=false", "build"})
+    @DisabledOnOs(value = { OS.WINDOWS })
     @Order(4)
     void testIgnoreQuarkusSystemPropertyAtBuild(CLIResult cliResult) {
         cliResult.assertMessage("Keycloak is the best");
         cliResult.assertBuild();
     }
 
+    @Test
+    @Launch({"-Dquarkus.log.handler.console.\\\"console-2\\\".enable=false", "build"})
+    @EnabledOnOs(value = { OS.WINDOWS }, disabledReason = "Different handling of quotes within arguments on Windows")
+    @Order(4)
+    void testIgnoreQuarkusSystemPropertyAtBuildWin(CLIResult cliResult) {
+        cliResult.assertMessage("Keycloak is the best");
+        cliResult.assertBuild();
+    }
+
     @DryRun
     @Test
     @BeforeStartDistribution(UpdateConsoleHandlerFromKeycloakConf.class)
@@ -145,11 +167,21 @@ public class QuarkusPropertiesDistTest {
     @Test
     @Launch({ "start", "--http-enabled=true", "--hostname-strict=false", "--config-keystore=/invalid/path",
             "--config-keystore-password=secret" })
+    @DisabledOnOs(value = { OS.WINDOWS })
     @Order(11)
     void testInvalidSmallRyeKeyStorePathProperty(CLIResult cliResult) {
         cliResult.assertError("java.lang.IllegalArgumentException: config-keystore path does not exist: /invalid/path");
     }
 
+    @Test
+    @Launch({ "start", "--http-enabled=true", "--hostname-strict=false", "--config-keystore=C:\\invalid\\path",
+            "--config-keystore-password=secret" })
+    @EnabledOnOs(value = { OS.WINDOWS }, disabledReason = "Windows uses a different path separator.")
+    @Order(11)
+    void testInvalidSmallRyeKeyStorePathPropertyWin(CLIResult cliResult) {
+        cliResult.assertError("java.lang.IllegalArgumentException: config-keystore path does not exist: C:\\invalid\\path");
+    }
+
     @Test
     @Launch({ "start", "--http-enabled=true", "--hostname-strict=false",
             "--config-keystore=../../../../src/test/resources/keystore", "--config-keystore-password=secret" })
@@ -173,7 +205,7 @@ public class QuarkusPropertiesDistTest {
 
     @Test
     @BeforeStartDistribution(ForceRebuild.class)
-    @DisabledOnOs(value = { OS.LINUX, OS.MAC }, disabledReason = "Windows uses a different path separator.")
+    @EnabledOnOs(value = { OS.WINDOWS }, disabledReason = "Windows uses a different path separator.")
     @Launch({ "start", "--http-enabled=true", "--hostname-strict=false",
             "--https-certificate-file=C:\\tmp\\kc\\bin\\..\\conf/server.crt.pem",
             "--https-certificate-key-file=C:\\tmp\\kc\\bin\\..\\conf/server.key.pem" })