diff --git a/src/commands/stepfunctions/__tests__/helpers.test.ts b/src/commands/stepfunctions/__tests__/helpers.test.ts
index 90d19bea7..1d0b05024 100644
--- a/src/commands/stepfunctions/__tests__/helpers.test.ts
+++ b/src/commands/stepfunctions/__tests__/helpers.test.ts
@@ -1,4 +1,5 @@
 import {DescribeStateMachineCommandOutput, LogLevel} from '@aws-sdk/client-sfn'
+import {BaseContext} from 'clipanion'
 
 import {
   buildArn,
@@ -16,7 +17,18 @@ import {
 
 import {describeStateMachineFixture} from './fixtures/aws-resources'
 
+const createMockContext = (): BaseContext => {
+  return {
+    stdout: {
+      write: (input: string) => {
+        return true
+      },
+    },
+  } as BaseContext
+}
+
 describe('stepfunctions command helpers tests', () => {
+  const context = createMockContext()
   describe('shouldUpdateStepForTracesMerging test', () => {
     test('already has JsonMerge added to payload field', () => {
       const step: StepType = {
@@ -28,7 +40,7 @@ describe('stepfunctions command helpers tests', () => {
         },
         End: true,
       }
-      expect(shouldUpdateStepForTracesMerging(step)).toBeFalsy()
+      expect(shouldUpdateStepForTracesMerging(step, context, 'Lambda Invoke')).toBeFalsy()
     })
 
     test('no payload field', () => {
@@ -40,7 +52,7 @@ describe('stepfunctions command helpers tests', () => {
         },
         End: true,
       }
-      expect(shouldUpdateStepForTracesMerging(step)).toBeTruthy()
+      expect(shouldUpdateStepForTracesMerging(step, context, 'Lambda Invoke')).toBeTruthy()
     })
 
     test('default payload field of $', () => {
@@ -53,7 +65,7 @@ describe('stepfunctions command helpers tests', () => {
         },
         End: true,
       }
-      expect(shouldUpdateStepForTracesMerging(step)).toBeTruthy()
+      expect(shouldUpdateStepForTracesMerging(step, context, 'Lambda Invoke')).toBeTruthy()
     })
 
     test('none-lambda step should not be updated', () => {
@@ -65,7 +77,7 @@ describe('stepfunctions command helpers tests', () => {
         },
         End: true,
       }
-      expect(shouldUpdateStepForTracesMerging(step)).toBeFalsy()
+      expect(shouldUpdateStepForTracesMerging(step, context, 'DynamoDB Update')).toBeFalsy()
     })
 
     test('legacy lambda api should not be updated', () => {
@@ -74,7 +86,7 @@ describe('stepfunctions command helpers tests', () => {
         Resource: 'arn:aws:lambda:sa-east-1:601427271234:function:hello-function',
         End: true,
       }
-      expect(shouldUpdateStepForTracesMerging(step)).toBeFalsy()
+      expect(shouldUpdateStepForTracesMerging(step, context, 'Legacy Lambda')).toBeFalsy()
     })
   })
 
@@ -185,7 +197,9 @@ describe('stepfunctions command helpers tests', () => {
         },
         End: true,
       }
-      expect(shouldUpdateStepForStepFunctionContextInjection(step)).toBeTruthy()
+      expect(
+        shouldUpdateStepForStepFunctionContextInjection(step, context, 'Step Functions StartExecution')
+      ).toBeTruthy()
     })
 
     test('is true for undefined', () => {
@@ -197,7 +211,9 @@ describe('stepfunctions command helpers tests', () => {
         },
         End: true,
       }
-      expect(shouldUpdateStepForStepFunctionContextInjection(step)).toBeTruthy()
+      expect(
+        shouldUpdateStepForStepFunctionContextInjection(step, context, 'Step Functions StartExecution')
+      ).toBeTruthy()
     })
 
     test('is false when Input is an object that contains a CONTEXT key', () => {
@@ -210,7 +226,9 @@ describe('stepfunctions command helpers tests', () => {
         },
         End: true,
       }
-      expect(shouldUpdateStepForStepFunctionContextInjection(step)).toBeFalsy()
+      expect(
+        shouldUpdateStepForStepFunctionContextInjection(step, context, 'Step Functions StartExecution')
+      ).toBeFalsy()
     })
   })
 
@@ -226,7 +244,7 @@ describe('stepfunctions command helpers tests', () => {
         End: true,
       }
 
-      const changed = injectContextForStepFunctions(step)
+      const changed = injectContextForStepFunctions(step, context, 'Step Functions StartExecution')
       expect(changed).toBeTruthy()
       expect(step.Parameters?.Input).toEqual({'CONTEXT.$': 'States.JsonMerge($$, $, false)'})
     })
diff --git a/src/commands/stepfunctions/helpers.ts b/src/commands/stepfunctions/helpers.ts
index 9e4158ded..5da8aba5c 100644
--- a/src/commands/stepfunctions/helpers.ts
+++ b/src/commands/stepfunctions/helpers.ts
@@ -95,7 +95,7 @@ export const injectContextIntoTasks = async (
     if (definitionObj.States.hasOwnProperty(stepName)) {
       const step = definitionObj.States[stepName]
       const lambdaUpdated = injectContextForLambdaFunctions(step, context, stepName)
-      const stepUpdated = injectContextForStepFunctions(step)
+      const stepUpdated = injectContextForStepFunctions(step, context, stepName)
       definitionHasBeenUpdated = lambdaUpdated || stepUpdated
     }
   }
@@ -125,20 +125,35 @@ export const addTraceContextToStepFunctionParameters = ({Parameters}: StepType):
   }
 }
 
-export const shouldUpdateStepForTracesMerging = (step: StepType): boolean => {
+export const shouldUpdateStepForTracesMerging = (step: StepType, context: BaseContext, stepName: string): boolean => {
   // is default lambda api
   if (step.Resource === 'arn:aws:states:::lambda:invoke') {
     if (!step.Parameters) {
+      context.stdout
+        .write(`[Warn] Step ${stepName} does not have a Parameters field. Step Functions Context Object injection \
+skipped. Your Step Functions trace will not be merged with downstream Lambda traces. To manually merge these traces, \
+check out https://docs.datadoghq.com/serverless/step_functions/troubleshooting/\n`)
+
       return false
     }
+
     // payload field not set
     if (!step.Parameters.hasOwnProperty('Payload.$')) {
       return true
     }
+
     // default payload
     if (step.Parameters['Payload.$'] === '$') {
       return true
     }
+
+    // custom payload
+    context.stdout
+      .write(`[Warn] Step ${stepName} has a custom Payload field. Step Functions Context Object injection skipped. \
+Your Step Functions trace will not be merged with downstream Lambda traces. To manually merge these traces, \
+check out https://docs.datadoghq.com/serverless/step_functions/troubleshooting/\n`)
+
+    return false
   }
 
   return false
@@ -152,21 +167,45 @@ export const shouldUpdateStepForTracesMerging = (step: StepType): boolean => {
 // not object               | false
 // object without CONTEXT.$ | true
 // object with CONTEXT.$    | false
-export const shouldUpdateStepForStepFunctionContextInjection = (step: StepType): boolean => {
+export const shouldUpdateStepForStepFunctionContextInjection = (
+  step: StepType,
+  context: BaseContext,
+  stepName: string
+): boolean => {
   // is default lambda api
   if (step.Resource?.startsWith('arn:aws:states:::states:startExecution')) {
     if (!step.Parameters) {
+      context.stdout
+        .write(`[Warn] Step ${stepName} does not have a Parameters field. Step Functions Context Object injection \
+skipped. Your Step Functions trace will not be merged with downstream Step Function traces. To manually merge these \
+traces, check out https://docs.datadoghq.com/serverless/step_functions/troubleshooting/\n`)
+
       return false
     }
+
     if (!step.Parameters.Input) {
       return true
     }
+
     if (typeof step.Parameters.Input !== 'object') {
+      context.stdout
+        .write(`[Warn] Step ${stepName}'s Parameters.Input field is not a JSON object. Step Functions Context Object \
+injection skipped. Your Step Functions trace will not be merged with downstream Step Function traces. To manually \
+merge these traces, check out https://docs.datadoghq.com/serverless/step_functions/troubleshooting/\n`)
+
       return false
     }
+
     if (!step.Parameters.Input['CONTEXT.$']) {
       return true
     }
+
+    context.stdout
+      .write(`[Warn] Step ${stepName}'s Parameters.Input field has a custom CONTEXT field. Step Functions Context \
+Object injection skipped. Your Step Functions trace will not be merged with downstream Step Function traces. To \
+manually merge these traces, check out https://docs.datadoghq.com/serverless/step_functions/troubleshooting/\n`)
+
+    return false
   }
 
   return false
@@ -198,7 +237,7 @@ export type ParametersType = {
 }
 
 const injectContextForLambdaFunctions = (step: StepType, context: BaseContext, stepName: string): boolean => {
-  if (shouldUpdateStepForTracesMerging(step)) {
+  if (shouldUpdateStepForTracesMerging(step, context, stepName)) {
     addTraceContextToLambdaParameters(step)
 
     return true
@@ -213,8 +252,8 @@ const injectContextForLambdaFunctions = (step: StepType, context: BaseContext, s
   return false
 }
 
-export const injectContextForStepFunctions = (step: StepType): boolean => {
-  if (shouldUpdateStepForStepFunctionContextInjection(step)) {
+export const injectContextForStepFunctions = (step: StepType, context: BaseContext, stepName: string): boolean => {
+  if (shouldUpdateStepForStepFunctionContextInjection(step, context, stepName)) {
     addTraceContextToStepFunctionParameters(step)
 
     return true