diff --git a/spring-boot-project/spring-boot-tools/spring-boot-test-support/src/main/java/org/springframework/boot/testsupport/junit/DisabledOnOs.java b/spring-boot-project/spring-boot-tools/spring-boot-test-support/src/main/java/org/springframework/boot/testsupport/junit/DisabledOnOs.java
index d691eac3a8..0b0dd15b69 100644
--- a/spring-boot-project/spring-boot-tools/spring-boot-test-support/src/main/java/org/springframework/boot/testsupport/junit/DisabledOnOs.java
+++ b/spring-boot-project/spring-boot-tools/spring-boot-test-support/src/main/java/org/springframework/boot/testsupport/junit/DisabledOnOs.java
@@ -40,7 +40,7 @@ public @interface DisabledOnOs {
 	 * See {@link org.junit.jupiter.api.condition.DisabledOnOs#value()}.
 	 * @return os
 	 */
-	OS os();
+	OS[] os();
 
 	/**
 	 * Architecture of the operating system.
diff --git a/spring-boot-project/spring-boot-tools/spring-boot-test-support/src/main/java/org/springframework/boot/testsupport/junit/DisabledOnOsCondition.java b/spring-boot-project/spring-boot-tools/spring-boot-test-support/src/main/java/org/springframework/boot/testsupport/junit/DisabledOnOsCondition.java
index 3b644b2006..3968c0ba6a 100644
--- a/spring-boot-project/spring-boot-tools/spring-boot-test-support/src/main/java/org/springframework/boot/testsupport/junit/DisabledOnOsCondition.java
+++ b/spring-boot-project/spring-boot-tools/spring-boot-test-support/src/main/java/org/springframework/boot/testsupport/junit/DisabledOnOsCondition.java
@@ -18,6 +18,7 @@ package org.springframework.boot.testsupport.junit;
 
 import java.util.Optional;
 
+import org.junit.jupiter.api.condition.OS;
 import org.junit.jupiter.api.extension.ConditionEvaluationResult;
 import org.junit.jupiter.api.extension.ExecutionCondition;
 import org.junit.jupiter.api.extension.ExtensionContext;
@@ -42,11 +43,15 @@ class DisabledOnOsCondition implements ExecutionCondition {
 	private ConditionEvaluationResult evaluate(DisabledOnOs annotation) {
 		String architecture = System.getProperty("os.arch");
 		String os = System.getProperty("os.name");
-		if (annotation.os().isCurrentOs() && annotation.architecture().equals(architecture)) {
-			String reason = annotation.disabledReason().isEmpty()
-					? String.format("Disabled on OS = %s, architecture = %s", os, architecture)
-					: annotation.disabledReason();
-			return ConditionEvaluationResult.disabled(reason);
+		if (annotation.architecture().equals(architecture)) {
+			for (OS targetOs : annotation.os()) {
+				if (targetOs.isCurrentOs()) {
+					String reason = annotation.disabledReason().isEmpty()
+							? String.format("Disabled on OS = %s, architecture = %s", os, architecture)
+							: annotation.disabledReason();
+					return ConditionEvaluationResult.disabled(reason);
+				}
+			}
 		}
 		return ConditionEvaluationResult
 				.enabled(String.format("Enabled on OS = %s, architecture = %s", os, architecture));
diff --git a/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/embedded/jetty/SslServerCustomizerTests.java b/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/embedded/jetty/SslServerCustomizerTests.java
index 556384575a..5cc9815eb4 100644
--- a/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/embedded/jetty/SslServerCustomizerTests.java
+++ b/spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/embedded/jetty/SslServerCustomizerTests.java
@@ -57,8 +57,8 @@ class SslServerCustomizerTests {
 
 	@Test
 	@SuppressWarnings("rawtypes")
-	@DisabledOnOs(os = OS.LINUX, architecture = "aarch64",
-			disabledReason = "conscrypt doesn't support Linux aarch64, see https://github.com/google/conscrypt/issues/1051")
+	@DisabledOnOs(os = { OS.LINUX, OS.MAC }, architecture = "aarch64",
+			disabledReason = "conscrypt doesn't support Linux/macOS aarch64, see https://github.com/google/conscrypt/issues/1051")
 	void whenHttp2IsEnabledServerConnectorsHasSslAlpnH2AndHttpConnectionFactories() {
 		Http2 http2 = new Http2();
 		http2.setEnabled(true);
@@ -71,8 +71,8 @@ class SslServerCustomizerTests {
 	}
 
 	@Test
-	@DisabledOnOs(os = OS.LINUX, architecture = "aarch64",
-			disabledReason = "conscrypt doesn't support Linux aarch64, see https://github.com/google/conscrypt/issues/1051")
+	@DisabledOnOs(os = { OS.LINUX, OS.MAC }, architecture = "aarch64",
+			disabledReason = "conscrypt doesn't support Linux/macOS aarch64, see https://github.com/google/conscrypt/issues/1051")
 	void alpnConnectionFactoryHasNullDefaultProtocolToAllowNegotiationToHttp11() {
 		Http2 http2 = new Http2();
 		http2.setEnabled(true);