diff --git a/packages/@aws-cdk/assertions/lib/annotations.ts b/packages/@aws-cdk/assertions/lib/annotations.ts
index c656b15d6bab8..09f4309044e4a 100644
--- a/packages/@aws-cdk/assertions/lib/annotations.ts
+++ b/packages/@aws-cdk/assertions/lib/annotations.ts
@@ -102,10 +102,10 @@ function constructMessage(type: 'info' | 'warning' | 'error', message: any): {[k
 }
 
 function convertArrayToMessagesType(messages: SynthesisMessage[]): Messages {
-  return messages.reduce((obj, item) => {
+  return messages.reduce((obj, item, index) => {
     return {
       ...obj,
-      [item.id]: item,
+      [index]: item,
     };
   }, {}) as Messages;
 }
diff --git a/packages/@aws-cdk/assertions/lib/private/message.ts b/packages/@aws-cdk/assertions/lib/private/message.ts
index 9657a5d90ad99..1a14fe6be1b00 100644
--- a/packages/@aws-cdk/assertions/lib/private/message.ts
+++ b/packages/@aws-cdk/assertions/lib/private/message.ts
@@ -1,5 +1,5 @@
 import { SynthesisMessage } from '@aws-cdk/cx-api';
 
 export type Messages = {
-  [logicalId: string]: SynthesisMessage;
+  [key: string]: SynthesisMessage;
 }
diff --git a/packages/@aws-cdk/assertions/lib/private/messages.ts b/packages/@aws-cdk/assertions/lib/private/messages.ts
index 75c6fe3ae50b1..935b4a4b32fad 100644
--- a/packages/@aws-cdk/assertions/lib/private/messages.ts
+++ b/packages/@aws-cdk/assertions/lib/private/messages.ts
@@ -1,21 +1,22 @@
-import { MatchResult } from '../matcher';
+import { SynthesisMessage } from '@aws-cdk/cx-api';
 import { Messages } from './message';
-import { filterLogicalId, formatFailure, matchSection } from './section';
+import { formatFailure, matchSection } from './section';
 
-export function findMessage(messages: Messages, logicalId: string, props: any = {}): { [key: string]: { [key: string]: any } } {
-  const section: { [key: string]: {} } = messages;
-  const result = matchSection(filterLogicalId(section, logicalId), props);
+export function findMessage(messages: Messages, constructPath: string, props: any = {}): { [key: string]: { [key: string]: any } } {
+  const section: { [key: string]: SynthesisMessage } = messages;
+  const result = matchSection(filterPath(section, constructPath), props);
 
   if (!result.match) {
     return {};
   }
 
+  Object.values(result.matches).forEach((m) => handleTrace(m));
   return result.matches;
 }
 
-export function hasMessage(messages: Messages, logicalId: string, props: any): string | void {
-  const section: { [key: string]: {} } = messages;
-  const result = matchSection(filterLogicalId(section, logicalId), props);
+export function hasMessage(messages: Messages, constructPath: string, props: any): string | void {
+  const section: { [key: string]: SynthesisMessage } = messages;
+  const result = matchSection(filterPath(section, constructPath), props);
 
   if (result.match) {
     return;
@@ -25,17 +26,26 @@ export function hasMessage(messages: Messages, logicalId: string, props: any): s
     return 'No messages found in the stack';
   }
 
+  handleTrace(result.closestResult.target);
   return [
     `Stack has ${result.analyzedCount} messages, but none match as expected.`,
-    formatFailure(formatMessage(result.closestResult)),
+    formatFailure(result.closestResult),
   ].join('\n');
 }
 
 // We redact the stack trace by default because it is unnecessarily long and unintelligible.
 // If there is a use case for rendering the trace, we can add it later.
-function formatMessage(match: MatchResult, renderTrace: boolean = false): MatchResult {
-  if (!renderTrace) {
-    match.target.entry.trace = 'redacted';
-  }
-  return match;
+function handleTrace(match: any, redact: boolean = true): void {
+  if (redact && match.entry?.trace !== undefined) {
+    match.entry.trace = 'redacted';
+  };
+}
+
+function filterPath(section: { [key: string]: SynthesisMessage }, path: string): { [key: string]: SynthesisMessage } {
+  // default signal for all paths is '*'
+  if (path === '*') return section;
+
+  return Object.entries(section ?? {})
+    .filter(([_, v]) => v.id === path)
+    .reduce((agg, [k, v]) => { return { ...agg, [k]: v }; }, {});
 }
diff --git a/packages/@aws-cdk/assertions/test/annotations.test.ts b/packages/@aws-cdk/assertions/test/annotations.test.ts
index 8275e52d39dff..615cd069bdaa4 100644
--- a/packages/@aws-cdk/assertions/test/annotations.test.ts
+++ b/packages/@aws-cdk/assertions/test/annotations.test.ts
@@ -7,12 +7,13 @@ describe('Messages', () => {
   let annotations: _Annotations;
   beforeAll(() => {
     stack = new Stack();
-    new CfnResource(stack, 'Foo', {
+    const foo = new CfnResource(stack, 'Foo', {
       type: 'Foo::Bar',
       properties: {
         Fred: 'Thud',
       },
     });
+    foo.node.setContext('disable-stack-trace', false);
 
     new CfnResource(stack, 'Bar', {
       type: 'Foo::Bar',
@@ -53,12 +54,17 @@ describe('Messages', () => {
   describe('findError', () => {
     test('match', () => {
       const result = annotations.findError('*', Match.anyValue());
-      expect(Object.keys(result).length).toEqual(2);
+      expect(result.length).toEqual(2);
     });
 
     test('no match', () => {
       const result = annotations.findError('*', 'no message looks like this');
-      expect(Object.keys(result).length).toEqual(0);
+      expect(result.length).toEqual(0);
+    });
+
+    test('trace is redacted', () => {
+      const result = annotations.findError('/Default/Foo', Match.anyValue());
+      expect(result[0].entry.trace).toEqual('redacted');
     });
   });
 
@@ -75,12 +81,12 @@ describe('Messages', () => {
   describe('findWarning', () => {
     test('match', () => {
       const result = annotations.findWarning('*', Match.anyValue());
-      expect(Object.keys(result).length).toEqual(1);
+      expect(result.length).toEqual(1);
     });
 
     test('no match', () => {
       const result = annotations.findWarning('*', 'no message looks like this');
-      expect(Object.keys(result).length).toEqual(0);
+      expect(result.length).toEqual(0);
     });
   });
 
@@ -97,19 +103,19 @@ describe('Messages', () => {
   describe('findInfo', () => {
     test('match', () => {
       const result = annotations.findInfo('/Default/Qux', 'this is an info');
-      expect(Object.keys(result).length).toEqual(1);
+      expect(result.length).toEqual(1);
     });
 
     test('no match', () => {
       const result = annotations.findInfo('*', 'no message looks like this');
-      expect(Object.keys(result).length).toEqual(0);
+      expect(result.length).toEqual(0);
     });
   });
 
   describe('with matchers', () => {
     test('anyValue', () => {
       const result = annotations.findError('*', Match.anyValue());
-      expect(Object.keys(result).length).toEqual(2);
+      expect(result.length).toEqual(2);
     });
 
     test('not', () => {
@@ -123,6 +129,53 @@ describe('Messages', () => {
   });
 });
 
+describe('Multiple Messages on the Resource', () => {
+  let stack: Stack;
+  let annotations: _Annotations;
+  beforeAll(() => {
+    stack = new Stack();
+    new CfnResource(stack, 'Foo', {
+      type: 'Foo::Bar',
+      properties: {
+        Fred: 'Thud',
+      },
+    });
+
+    const bar = new CfnResource(stack, 'Bar', {
+      type: 'Foo::Bar',
+      properties: {
+        Baz: 'Qux',
+      },
+    });
+    bar.node.setContext('disable-stack-trace', false);
+
+    Aspects.of(stack).add(new MultipleAspectsPerNode());
+    annotations = _Annotations.fromStack(stack);
+  });
+
+  test('succeeds on hasXxx APIs', () => {
+    annotations.hasError('/Default/Foo', 'error: this is an error');
+    annotations.hasError('/Default/Foo', 'error: unsupported type Foo::Bar');
+    annotations.hasWarning('/Default/Foo', 'warning: Foo::Bar is deprecated');
+  });
+
+  test('succeeds on findXxx APIs', () => {
+    const result1 = annotations.findError('*', Match.stringLikeRegexp('error:.*'));
+    expect(result1.length).toEqual(4);
+    const result2 = annotations.findError('/Default/Bar', Match.stringLikeRegexp('error:.*'));
+    expect(result2.length).toEqual(2);
+    const result3 = annotations.findWarning('/Default/Bar', 'warning: Foo::Bar is deprecated');
+    expect(result3).toEqual([{
+      level: 'warning',
+      entry: {
+        type: 'aws:cdk:warning',
+        data: 'warning: Foo::Bar is deprecated',
+        trace: 'redacted',
+      },
+      id: '/Default/Bar',
+    }]);
+  });
+});
 class MyAspect implements IAspect {
   public visit(node: IConstruct): void {
     if (node instanceof CfnResource) {
@@ -147,4 +200,22 @@ class MyAspect implements IAspect {
   protected info(node: IConstruct, message: string): void {
     Annotations.of(node).addInfo(message);
   }
+}
+
+class MultipleAspectsPerNode implements IAspect {
+  public visit(node: IConstruct): void {
+    if (node instanceof CfnResource) {
+      this.error(node, 'error: this is an error');
+      this.error(node, `error: unsupported type ${node.cfnResourceType}`);
+      this.warn(node, `warning: ${node.cfnResourceType} is deprecated`);
+    }
+  }
+
+  protected warn(node: IConstruct, message: string): void {
+    Annotations.of(node).addWarning(message);
+  }
+
+  protected error(node: IConstruct, message: string): void {
+    Annotations.of(node).addError(message);
+  }
 }
\ No newline at end of file