diff --git a/CHANGELOG.md b/CHANGELOG.md
index be27e02..ebefa34 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -15,6 +15,7 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 - Snippets: `devproxy-plugin-rewrite-file` - RewritePlugin rewrites file
 - Snippets: `devproxy-plugin-rewrite-file-schema` - RewritePlugin rewrites file schema
 - Diagnostics: Show warning if config contains a summary plugin without a reporter
+- Diagnostics: Show warning if OpenApiSpecGeneratorPlugin is placed after ApiCenterOnboardingPlugin
 
 ### Changed: 
 
diff --git a/README.md b/README.md
index 71226e9..3b7d174 100644
--- a/README.md
+++ b/README.md
@@ -39,6 +39,7 @@ The following sections describe the features that the extension contributes to V
 - Check that a plugin can be configured with a configSection
 - Check for configSections that are not used in plugins
 - Check for reporter plugin when a summary plugin is used
+- Check that ApiCenterOnboardingPlugin is placed after OpenApiSpecGeneratorPlugin
 
 ### Editor Actions
 
diff --git a/src/diagnostics.ts b/src/diagnostics.ts
index 472c15f..ee0f000 100644
--- a/src/diagnostics.ts
+++ b/src/diagnostics.ts
@@ -107,6 +107,7 @@ const checkPlugins = (pluginsNode: parse.PropertyNode | undefined, diagnostics:
     warnOnReporterPosition(pluginNodes, diagnostics);
     validatePluginConfigurations(pluginNodes, diagnostics, documentNode);
     checkForSummaryPluginWithoutReporter(pluginNodes, diagnostics);
+    checkAPICOnboardingPluginAfterOpenApiSpecGeneratorPlugin(pluginNodes, diagnostics);
   }
 };
 
@@ -341,4 +342,47 @@ function checkForSummaryPluginWithoutReporter(pluginNodes: parse.ObjectNode[], d
       );
     }
   }
+}
+
+function checkAPICOnboardingPluginAfterOpenApiSpecGeneratorPlugin(pluginNodes: parse.ObjectNode[], diagnostics: vscode.Diagnostic[]) {
+  const openApiSpecGeneratorPluginIndex = pluginNodes.findIndex((pluginNode: parse.ObjectNode) => {
+    const pluginNameNode = getASTNode(
+      pluginNode.children,
+      'Identifier',
+      'name'
+    );
+    const pluginName = (pluginNameNode?.value as parse.LiteralNode)
+      .value as string;
+    const enabledNode = getASTNode(
+      pluginNode.children,
+      'Identifier',
+      'enabled'
+    );
+    const isEnabled = (enabledNode?.value as parse.LiteralNode)
+      .value as boolean;
+    return pluginName === 'OpenApiSpecGeneratorPlugin' && isEnabled;
+  }
+  );
+  if (openApiSpecGeneratorPluginIndex !== -1) {
+    const apiCenterOnboardingPluginIndex = pluginNodes.findIndex((pluginNode: parse.ObjectNode) => {
+      const pluginNameNode = getASTNode(
+        pluginNode.children,
+        'Identifier',
+        'name'
+      );
+      const pluginName = (pluginNameNode?.value as parse.LiteralNode)
+        .value as string;
+      return pluginName === 'ApiCenterOnboardingPlugin';
+    }
+    );
+    if (apiCenterOnboardingPluginIndex !== -1 && apiCenterOnboardingPluginIndex < openApiSpecGeneratorPluginIndex) {
+      diagnostics.push(
+        new vscode.Diagnostic(
+          getRangeFromASTNode(pluginNodes[openApiSpecGeneratorPluginIndex]),
+          'OpenApiSpecGeneratorPlugin should be placed before ApiCenterOnboardingPlugin.',
+          vscode.DiagnosticSeverity.Warning
+        )
+      );
+    }
+  }
 }
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