diff --git a/maven-core/src/main/java/org/apache/maven/toolchain/DefaultToolchainManager.java b/maven-core/src/main/java/org/apache/maven/toolchain/DefaultToolchainManager.java
index 3c1a36ffa18b..3c30f442b78d 100644
--- a/maven-core/src/main/java/org/apache/maven/toolchain/DefaultToolchainManager.java
+++ b/maven-core/src/main/java/org/apache/maven/toolchain/DefaultToolchainManager.java
@@ -88,7 +88,8 @@ private List<Toolchain> selectToolchains(
                             toolchains.add(toolchain);
                         }
                     } catch (MisconfiguredToolchainException ex) {
-                        logger.error("Misconfigured toolchain.", ex);
+                        throw new IllegalStateException(
+                                "Misconfigured toolchain of type " + type + ": " + ex.getMessage(), ex);
                     }
                 }
             }
diff --git a/maven-core/src/main/java/org/apache/maven/toolchain/ToolchainManager.java b/maven-core/src/main/java/org/apache/maven/toolchain/ToolchainManager.java
index e760b6b9a435..dfeabc7cd157 100644
--- a/maven-core/src/main/java/org/apache/maven/toolchain/ToolchainManager.java
+++ b/maven-core/src/main/java/org/apache/maven/toolchain/ToolchainManager.java
@@ -44,6 +44,7 @@ public interface ToolchainManager {
      * @param type the type, must not be {@code null}
      * @param context the Maven session, must not be {@code null}
      * @return the toolchain selected by <code>maven-toolchains-plugin</code>
+     * @throws IllegalStateException if the configured toolchain cannot be created
      */
     Toolchain getToolchainFromBuildContext(String type, MavenSession context);
 
@@ -55,6 +56,7 @@ public interface ToolchainManager {
      * @param type the type, must not be {@code null}
      * @param requirements the requirements, may be {@code null}
      * @return the matching toolchains, never {@code null}
+     * @throws IllegalStateException if a configured toolchain cannot be created
      * @since 3.3.0
      */
     List<Toolchain> getToolchains(MavenSession session, String type, Map<String, String> requirements);
diff --git a/maven-core/src/test/java/org/apache/maven/toolchain/DefaultToolchainManagerTest.java b/maven-core/src/test/java/org/apache/maven/toolchain/DefaultToolchainManagerTest.java
index 5a2b5ab680e5..1facf1eacd2c 100644
--- a/maven-core/src/test/java/org/apache/maven/toolchain/DefaultToolchainManagerTest.java
+++ b/maven-core/src/test/java/org/apache/maven/toolchain/DefaultToolchainManagerTest.java
@@ -18,6 +18,7 @@
  */
 package org.apache.maven.toolchain;
 
+import java.nio.file.Path;
 import java.util.Arrays;
 import java.util.Collections;
 import java.util.HashMap;
@@ -27,16 +28,22 @@
 import org.apache.maven.execution.DefaultMavenExecutionRequest;
 import org.apache.maven.execution.MavenExecutionRequest;
 import org.apache.maven.execution.MavenSession;
+import org.apache.maven.toolchain.java.JavaToolchainFactory;
 import org.apache.maven.toolchain.model.ToolchainModel;
 import org.codehaus.plexus.logging.Logger;
+import org.codehaus.plexus.util.xml.Xpp3Dom;
 import org.junit.jupiter.api.BeforeEach;
 import org.junit.jupiter.api.Test;
+import org.junit.jupiter.api.io.TempDir;
 import org.mockito.ArgumentMatchers;
 import org.mockito.InjectMocks;
 import org.mockito.Mock;
 import org.mockito.MockitoAnnotations;
 
 import static org.junit.jupiter.api.Assertions.assertEquals;
+import static org.junit.jupiter.api.Assertions.assertInstanceOf;
+import static org.junit.jupiter.api.Assertions.assertThrows;
+import static org.junit.jupiter.api.Assertions.assertTrue;
 import static org.mockito.ArgumentMatchers.isA;
 import static org.mockito.Mockito.mock;
 import static org.mockito.Mockito.verify;
@@ -144,4 +151,52 @@ public void testRequirements() throws Exception {
 
         assertEquals(1, toolchains.size());
     }
+
+    @Test
+    public void testMatchingMisconfiguredJdkToolchain(@TempDir Path temporaryDirectory) {
+        Path invalidJdkHome = temporaryDirectory.resolve("non-existing-jdk");
+        ToolchainModel model = new ToolchainModel();
+        model.setType("jdk");
+        model.addProvide("version", "17");
+
+        Xpp3Dom jdkHome = new Xpp3Dom("jdkHome");
+        jdkHome.setValue(invalidJdkHome.toString());
+        Xpp3Dom configuration = new Xpp3Dom("configuration");
+        configuration.addChild(jdkHome);
+        model.setConfiguration(configuration);
+
+        MavenSession session = mock(MavenSession.class);
+        MavenExecutionRequest executionRequest = new DefaultMavenExecutionRequest();
+        executionRequest.setToolchains(Collections.singletonMap("jdk", Collections.singletonList(model)));
+        when(session.getRequest()).thenReturn(executionRequest);
+        toolchainManager.factories.put("jdk", new JavaToolchainFactory());
+
+        IllegalStateException exception = assertThrows(
+                IllegalStateException.class,
+                () -> toolchainManager.getToolchains(session, "jdk", Collections.singletonMap("version", "17")));
+
+        assertTrue(exception.getMessage().contains("Misconfigured toolchain of type jdk"));
+        assertTrue(exception.getMessage().contains(invalidJdkHome.toString()));
+        assertInstanceOf(MisconfiguredToolchainException.class, exception.getCause());
+    }
+
+    @Test
+    public void testValidNonmatchingToolchain() throws Exception {
+        ToolchainModel model = new ToolchainModel();
+        model.setType("basic");
+
+        MavenSession session = mock(MavenSession.class);
+        MavenExecutionRequest executionRequest = new DefaultMavenExecutionRequest();
+        executionRequest.setToolchains(Collections.singletonMap("basic", Collections.singletonList(model)));
+        when(session.getRequest()).thenReturn(executionRequest);
+        ToolchainPrivate toolchain = mock(ToolchainPrivate.class);
+        when(toolchainFactoryBasicType.createToolchain(model)).thenReturn(toolchain);
+        when(toolchain.matchesRequirements(Collections.singletonMap("version", "21")))
+                .thenReturn(false);
+
+        List<Toolchain> toolchains =
+                toolchainManager.getToolchains(session, "basic", Collections.singletonMap("version", "21"));
+
+        assertEquals(0, toolchains.size());
+    }
 }