diff --git a/flink-table/flink-sql-gateway/src/main/java/org/apache/flink/table/gateway/service/context/SessionContext.java b/flink-table/flink-sql-gateway/src/main/java/org/apache/flink/table/gateway/service/context/SessionContext.java
index b5463d44267fe..7cf2d5c7b38ed 100644
--- a/flink-table/flink-sql-gateway/src/main/java/org/apache/flink/table/gateway/service/context/SessionContext.java
+++ b/flink-table/flink-sql-gateway/src/main/java/org/apache/flink/table/gateway/service/context/SessionContext.java
@@ -56,6 +56,8 @@
 import javax.annotation.Nullable;
 
 import java.io.IOException;
+import java.net.MalformedURLException;
+import java.net.URI;
 import java.net.URL;
 import java.net.URLClassLoader;
 import java.nio.file.Path;
@@ -304,7 +306,7 @@ public static SessionContext create(
                 initializeConfiguration(defaultContext, environment, sessionId);
         final MutableURLClassLoader userClassLoader =
                 FlinkUserCodeClassLoaders.create(
-                        defaultContext.getDependencies().toArray(new URL[0]),
+                        getDependencyURLs(defaultContext),
                         SessionContext.class.getClassLoader(),
                         configuration);
         final ResourceManager resourceManager = new ResourceManager(configuration, userClassLoader);
@@ -318,6 +320,21 @@ public static SessionContext create(
                 new OperationManager(operationExecutorService));
     }
 
+    private static URL[] getDependencyURLs(DefaultContext defaultContext) {
+        return defaultContext.getDependencies().stream()
+                .map(SessionContext::toURL)
+                .toArray(URL[]::new);
+    }
+
+    private static URL toURL(URI uri) {
+        try {
+            return uri.toURL();
+        } catch (MalformedURLException | IllegalArgumentException e) {
+            throw new SqlGatewayException(
+                    String.format("Failed to convert dependency URI '%s' to URL.", uri), e);
+        }
+    }
+
     // ------------------------------------------------------------------------------------------------------------------
     // Helpers
     // ------------------------------------------------------------------------------------------------------------------
diff --git a/flink-table/flink-sql-gateway/src/test/java/org/apache/flink/table/gateway/service/context/SessionContextTest.java b/flink-table/flink-sql-gateway/src/test/java/org/apache/flink/table/gateway/service/context/SessionContextTest.java
index 74ff1a16807b1..3f2dffd4d2a7b 100644
--- a/flink-table/flink-sql-gateway/src/test/java/org/apache/flink/table/gateway/service/context/SessionContextTest.java
+++ b/flink-table/flink-sql-gateway/src/test/java/org/apache/flink/table/gateway/service/context/SessionContextTest.java
@@ -32,6 +32,7 @@
 import org.apache.flink.table.gateway.api.session.SessionEnvironment;
 import org.apache.flink.table.gateway.api.session.SessionHandle;
 import org.apache.flink.table.gateway.api.utils.MockedEndpointVersion;
+import org.apache.flink.table.gateway.api.utils.SqlGatewayException;
 import org.apache.flink.table.gateway.api.utils.ThreadUtils;
 
 import org.junit.jupiter.api.AfterAll;
@@ -40,6 +41,7 @@
 import org.junit.jupiter.api.Test;
 import org.junit.jupiter.api.io.TempDir;
 
+import java.net.URI;
 import java.nio.file.Path;
 import java.util.Arrays;
 import java.util.Collections;
@@ -54,6 +56,7 @@
 import static org.apache.flink.table.api.config.TableConfigOptions.TABLE_SQL_DIALECT;
 import static org.apache.flink.table.catalog.CommonCatalogOptions.TABLE_CATALOG_STORE_KIND;
 import static org.assertj.core.api.Assertions.assertThat;
+import static org.assertj.core.api.Assertions.assertThatThrownBy;
 
 /** Test {@link SessionContext}. */
 class SessionContextTest {
@@ -146,6 +149,50 @@ void testSetAndResetArbitraryKey() {
                 .matches((conf) -> !conf.containsKey("aa") && !conf.containsKey("bb"));
     }
 
+    @Test
+    void testCreateContextWithDependencies(@TempDir Path dependencyDirectory) throws Exception {
+        DefaultContext defaultContext =
+                new DefaultContext(
+                        new Configuration(),
+                        Collections.singletonList(dependencyDirectory.toUri()));
+        SessionEnvironment environment =
+                SessionEnvironment.newBuilder()
+                        .setSessionEndpointVersion(MockedEndpointVersion.V1)
+                        .build();
+
+        SessionContext context =
+                SessionContext.create(
+                        defaultContext, SessionHandle.create(), environment, EXECUTOR_SERVICE);
+        try {
+            assertThat(context.getUserClassloader().getURLs())
+                    .contains(dependencyDirectory.toUri().toURL());
+        } finally {
+            context.close();
+        }
+    }
+
+    @Test
+    void testCreateContextWrapsSchemelessDependencyUri() {
+        DefaultContext defaultContext =
+                new DefaultContext(
+                        new Configuration(), Collections.singletonList(URI.create("foo.jar")));
+        SessionEnvironment environment =
+                SessionEnvironment.newBuilder()
+                        .setSessionEndpointVersion(MockedEndpointVersion.V1)
+                        .build();
+
+        assertThatThrownBy(
+                        () ->
+                                SessionContext.create(
+                                        defaultContext,
+                                        SessionHandle.create(),
+                                        environment,
+                                        EXECUTOR_SERVICE))
+                .isInstanceOf(SqlGatewayException.class)
+                .hasMessageContaining("Failed to convert dependency URI 'foo.jar' to URL.")
+                .hasCauseInstanceOf(IllegalArgumentException.class);
+    }
+
     @Test
     void testCreateContextWithListeners() {
         assertThat(