diff --git a/packages/@aws-cdk/aws-elasticloadbalancingv2-targets/test/lambda-target.integ.snapshot/TestStack.template.json b/packages/@aws-cdk/aws-elasticloadbalancingv2-targets/test/lambda-target.integ.snapshot/TestStack.template.json
index 4821811c93ba4..8df70b33218b2 100644
--- a/packages/@aws-cdk/aws-elasticloadbalancingv2-targets/test/lambda-target.integ.snapshot/TestStack.template.json
+++ b/packages/@aws-cdk/aws-elasticloadbalancingv2-targets/test/lambda-target.integ.snapshot/TestStack.template.json
@@ -445,7 +445,7 @@
     "TargetType": "lambda"
    },
    "DependsOn": [
-    "FunInvokeServicePrincipalelasticloadbalancingamazonawscomD2CAC0C4"
+    "FunInvoke2UTWxhlfyqbT5FTn5jvgbLgjFfJwzswGk55DU1HY1CA1AAFB"
    ]
   },
   "FunServiceRole3CC876D7": {
@@ -498,7 +498,7 @@
     "FunServiceRole3CC876D7"
    ]
   },
-  "FunInvokeServicePrincipalelasticloadbalancingamazonawscomD2CAC0C4": {
+  "FunInvoke2UTWxhlfyqbT5FTn5jvgbLgjFfJwzswGk55DU1HY1CA1AAFB": {
    "Type": "AWS::Lambda::Permission",
    "Properties": {
     "Action": "lambda:InvokeFunction",
diff --git a/packages/@aws-cdk/aws-elasticloadbalancingv2-targets/test/lambda-target.integ.snapshot/cdk.out b/packages/@aws-cdk/aws-elasticloadbalancingv2-targets/test/lambda-target.integ.snapshot/cdk.out
index 90bef2e09ad39..2efc89439fab8 100644
--- a/packages/@aws-cdk/aws-elasticloadbalancingv2-targets/test/lambda-target.integ.snapshot/cdk.out
+++ b/packages/@aws-cdk/aws-elasticloadbalancingv2-targets/test/lambda-target.integ.snapshot/cdk.out
@@ -1 +1 @@
-{"version":"17.0.0"}
\ No newline at end of file
+{"version":"18.0.0"}
\ No newline at end of file
diff --git a/packages/@aws-cdk/aws-elasticloadbalancingv2-targets/test/lambda-target.integ.snapshot/integ.json b/packages/@aws-cdk/aws-elasticloadbalancingv2-targets/test/lambda-target.integ.snapshot/integ.json
index 3998c2a4aadd9..83d2bae05f09e 100644
--- a/packages/@aws-cdk/aws-elasticloadbalancingv2-targets/test/lambda-target.integ.snapshot/integ.json
+++ b/packages/@aws-cdk/aws-elasticloadbalancingv2-targets/test/lambda-target.integ.snapshot/integ.json
@@ -1,7 +1,7 @@
 {
   "version": "18.0.0",
   "testCases": {
-    "aws-elasticloadbalancingv2-targets/test/integ.lambda-target": {
+    "integ.lambda-target": {
       "stacks": [
         "TestStack"
       ],
diff --git a/packages/@aws-cdk/aws-elasticloadbalancingv2-targets/test/lambda-target.integ.snapshot/manifest.json b/packages/@aws-cdk/aws-elasticloadbalancingv2-targets/test/lambda-target.integ.snapshot/manifest.json
index f4d387a845efb..23c2e6d9ba570 100644
--- a/packages/@aws-cdk/aws-elasticloadbalancingv2-targets/test/lambda-target.integ.snapshot/manifest.json
+++ b/packages/@aws-cdk/aws-elasticloadbalancingv2-targets/test/lambda-target.integ.snapshot/manifest.json
@@ -1,5 +1,5 @@
 {
-  "version": "17.0.0",
+  "version": "18.0.0",
   "artifacts": {
     "Tree": {
       "type": "cdk:tree",
@@ -177,10 +177,19 @@
             "data": "FunA2CCED21"
           }
         ],
-        "/TestStack/Fun/InvokeServicePrincipal(elasticloadbalancing.amazonaws.com)": [
+        "/TestStack/Fun/Invoke2UTWxhlfyqbT5FTn--5jvgbLgj+FfJwzswGk55DU1H--Y=": [
           {
             "type": "aws:cdk:logicalId",
-            "data": "FunInvokeServicePrincipalelasticloadbalancingamazonawscomD2CAC0C4"
+            "data": "FunInvoke2UTWxhlfyqbT5FTn5jvgbLgjFfJwzswGk55DU1HY1CA1AAFB"
+          }
+        ],
+        "FunInvokeServicePrincipalelasticloadbalancingamazonawscomD2CAC0C4": [
+          {
+            "type": "aws:cdk:logicalId",
+            "data": "FunInvokeServicePrincipalelasticloadbalancingamazonawscomD2CAC0C4",
+            "trace": [
+              "!!DESTRUCTIVE_CHANGES: WILL_DESTROY"
+            ]
           }
         ]
       },
diff --git a/packages/@aws-cdk/aws-elasticloadbalancingv2-targets/test/lambda-target.integ.snapshot/tree.json b/packages/@aws-cdk/aws-elasticloadbalancingv2-targets/test/lambda-target.integ.snapshot/tree.json
index 9b4128b94f2ce..d2070dc0a6410 100644
--- a/packages/@aws-cdk/aws-elasticloadbalancingv2-targets/test/lambda-target.integ.snapshot/tree.json
+++ b/packages/@aws-cdk/aws-elasticloadbalancingv2-targets/test/lambda-target.integ.snapshot/tree.json
@@ -850,9 +850,9 @@
                   "version": "0.0.0"
                 }
               },
-              "InvokeServicePrincipal(elasticloadbalancing.amazonaws.com)": {
-                "id": "InvokeServicePrincipal(elasticloadbalancing.amazonaws.com)",
-                "path": "TestStack/Fun/InvokeServicePrincipal(elasticloadbalancing.amazonaws.com)",
+              "Invoke2UTWxhlfyqbT5FTn--5jvgbLgj+FfJwzswGk55DU1H--Y=": {
+                "id": "Invoke2UTWxhlfyqbT5FTn--5jvgbLgj+FfJwzswGk55DU1H--Y=",
+                "path": "TestStack/Fun/Invoke2UTWxhlfyqbT5FTn--5jvgbLgj+FfJwzswGk55DU1H--Y=",
                 "attributes": {
                   "aws:cdk:cloudformation:type": "AWS::Lambda::Permission",
                   "aws:cdk:cloudformation:props": {
diff --git a/packages/@aws-cdk/aws-lambda/lib/function-base.ts b/packages/@aws-cdk/aws-lambda/lib/function-base.ts
index f53bc54a18012..e8745f366c4dd 100644
--- a/packages/@aws-cdk/aws-lambda/lib/function-base.ts
+++ b/packages/@aws-cdk/aws-lambda/lib/function-base.ts
@@ -1,3 +1,4 @@
+import { createHash } from 'crypto';
 import * as cloudwatch from '@aws-cdk/aws-cloudwatch';
 import * as ec2 from '@aws-cdk/aws-ec2';
 import * as iam from '@aws-cdk/aws-iam';
@@ -414,7 +415,13 @@ export abstract class FunctionBase extends Resource implements IFunction, ec2.IC
    * Grant the given identity permissions to invoke this Lambda
    */
   public grantInvoke(grantee: iam.IGrantable): iam.Grant {
-    const identifier = `Invoke${grantee.grantPrincipal}`; // calls the .toString() of the principal
+    const hash = createHash('sha256')
+      .update(JSON.stringify({
+        principal: grantee.grantPrincipal.toString(),
+        conditions: grantee.grantPrincipal.policyFragment.conditions,
+      }), 'utf8')
+      .digest('base64');
+    const identifier = `Invoke${hash}`;
 
     // Memoize the result so subsequent grantInvoke() calls are idempotent
     let grant = this._invocationGrants[identifier];
diff --git a/packages/@aws-cdk/aws-lambda/test/function.test.ts b/packages/@aws-cdk/aws-lambda/test/function.test.ts
index e783535926eef..78f17b5f55394 100644
--- a/packages/@aws-cdk/aws-lambda/test/function.test.ts
+++ b/packages/@aws-cdk/aws-lambda/test/function.test.ts
@@ -2755,6 +2755,75 @@ describe('function', () => {
       });
     });
   });
+
+  test('called twice for the same service principal but with different conditions', () => {
+    // GIVEN
+    const stack = new cdk.Stack();
+    const fn = new lambda.Function(stack, 'Function', {
+      code: lambda.Code.fromInline('xxx'),
+      handler: 'index.handler',
+      runtime: lambda.Runtime.NODEJS_14_X,
+    });
+    const sourceArnA = 'some-arn-a';
+    const sourceArnB = 'some-arn-b';
+    const service = 's3.amazonaws.com';
+    const conditionalPrincipalA = new iam.PrincipalWithConditions(new iam.ServicePrincipal(service), {
+      ArnLike: {
+        'aws:SourceArn': sourceArnA,
+      },
+      StringEquals: {
+        'aws:SourceAccount': stack.account,
+      },
+    });
+    const conditionalPrincipalB = new iam.PrincipalWithConditions(new iam.ServicePrincipal(service), {
+      ArnLike: {
+        'aws:SourceArn': sourceArnB,
+      },
+      StringEquals: {
+        'aws:SourceAccount': stack.account,
+      },
+    });
+
+    // WHEN
+    fn.grantInvoke(conditionalPrincipalA);
+    fn.grantInvoke(conditionalPrincipalB);
+
+    // THEN
+    Template.fromStack(stack).resourceCountIs('AWS::Lambda::Permission', 2);
+    Template.fromStack(stack).hasResource('AWS::Lambda::Permission', {
+      Properties: {
+        Action: 'lambda:InvokeFunction',
+        FunctionName: {
+          'Fn::GetAtt': [
+            'Function76856677',
+            'Arn',
+          ],
+        },
+        Principal: service,
+        SourceAccount: {
+          Ref: 'AWS::AccountId',
+        },
+        SourceArn: sourceArnA,
+      },
+    });
+
+    Template.fromStack(stack).hasResource('AWS::Lambda::Permission', {
+      Properties: {
+        Action: 'lambda:InvokeFunction',
+        FunctionName: {
+          'Fn::GetAtt': [
+            'Function76856677',
+            'Arn',
+          ],
+        },
+        Principal: service,
+        SourceAccount: {
+          Ref: 'AWS::AccountId',
+        },
+        SourceArn: sourceArnB,
+      },
+    });
+  });
 });
 
 test('throws if ephemeral storage size is out of bound', () => {
diff --git a/packages/@aws-cdk/aws-lambda/test/lambda-version.test.ts b/packages/@aws-cdk/aws-lambda/test/lambda-version.test.ts
index 80a540fa5c6c8..d18e5301d971d 100644
--- a/packages/@aws-cdk/aws-lambda/test/lambda-version.test.ts
+++ b/packages/@aws-cdk/aws-lambda/test/lambda-version.test.ts
@@ -1,7 +1,7 @@
 import { Template } from '@aws-cdk/assertions';
+import { testDeprecated } from '@aws-cdk/cdk-build-tools';
 import * as cdk from '@aws-cdk/core';
 import * as lambda from '../lib';
-import { testDeprecated } from '@aws-cdk/cdk-build-tools';
 
 describe('lambda version', () => {
   test('can import a Lambda version by ARN', () => {
diff --git a/packages/@aws-cdk/aws-lambda/test/singleton-lambda.test.ts b/packages/@aws-cdk/aws-lambda/test/singleton-lambda.test.ts
index bd40f612558e1..fd65c207882ee 100644
--- a/packages/@aws-cdk/aws-lambda/test/singleton-lambda.test.ts
+++ b/packages/@aws-cdk/aws-lambda/test/singleton-lambda.test.ts
@@ -2,9 +2,9 @@ import { Template } from '@aws-cdk/assertions';
 import * as ec2 from '@aws-cdk/aws-ec2';
 import * as iam from '@aws-cdk/aws-iam';
 import * as s3 from '@aws-cdk/aws-s3';
+import { testDeprecated } from '@aws-cdk/cdk-build-tools';
 import * as cdk from '@aws-cdk/core';
 import * as lambda from '../lib';
-import { testDeprecated } from '@aws-cdk/cdk-build-tools';
 
 describe('singleton lambda', () => {
   test('can add same singleton Lambda multiple times, only instantiated once in template', () => {
diff --git a/packages/@aws-cdk/aws-secretsmanager/test/lambda-rotation.integ.snapshot/cdk-integ-secret-lambda-rotation.template.json b/packages/@aws-cdk/aws-secretsmanager/test/lambda-rotation.integ.snapshot/cdk-integ-secret-lambda-rotation.template.json
index c80e3bfc35786..207ca088201bf 100644
--- a/packages/@aws-cdk/aws-secretsmanager/test/lambda-rotation.integ.snapshot/cdk-integ-secret-lambda-rotation.template.json
+++ b/packages/@aws-cdk/aws-secretsmanager/test/lambda-rotation.integ.snapshot/cdk-integ-secret-lambda-rotation.template.json
@@ -266,7 +266,7 @@
     "LambdaServiceRoleA8ED4D3B"
    ]
   },
-  "LambdaInvokeServicePrincipalsecretsmanageramazonawscomB927629E": {
+  "LambdaInvokeN0a2GKfZP0JmDqDEVhhu6A0TUv3NyNbk4YMFKNc69846677": {
    "Type": "AWS::Lambda::Permission",
    "Properties": {
     "Action": "lambda:InvokeFunction",
diff --git a/packages/@aws-cdk/aws-secretsmanager/test/lambda-rotation.integ.snapshot/cdk.out b/packages/@aws-cdk/aws-secretsmanager/test/lambda-rotation.integ.snapshot/cdk.out
index 90bef2e09ad39..2efc89439fab8 100644
--- a/packages/@aws-cdk/aws-secretsmanager/test/lambda-rotation.integ.snapshot/cdk.out
+++ b/packages/@aws-cdk/aws-secretsmanager/test/lambda-rotation.integ.snapshot/cdk.out
@@ -1 +1 @@
-{"version":"17.0.0"}
\ No newline at end of file
+{"version":"18.0.0"}
\ No newline at end of file
diff --git a/packages/@aws-cdk/aws-secretsmanager/test/lambda-rotation.integ.snapshot/integ.json b/packages/@aws-cdk/aws-secretsmanager/test/lambda-rotation.integ.snapshot/integ.json
index b30c85877546a..483f26d467fce 100644
--- a/packages/@aws-cdk/aws-secretsmanager/test/lambda-rotation.integ.snapshot/integ.json
+++ b/packages/@aws-cdk/aws-secretsmanager/test/lambda-rotation.integ.snapshot/integ.json
@@ -1,7 +1,7 @@
 {
   "version": "18.0.0",
   "testCases": {
-    "aws-secretsmanager/test/integ.lambda-rotation": {
+    "integ.lambda-rotation": {
       "stacks": [
         "cdk-integ-secret-lambda-rotation"
       ],
diff --git a/packages/@aws-cdk/aws-secretsmanager/test/lambda-rotation.integ.snapshot/manifest.json b/packages/@aws-cdk/aws-secretsmanager/test/lambda-rotation.integ.snapshot/manifest.json
index c190e90ab3c0e..b10d2016e1aa9 100644
--- a/packages/@aws-cdk/aws-secretsmanager/test/lambda-rotation.integ.snapshot/manifest.json
+++ b/packages/@aws-cdk/aws-secretsmanager/test/lambda-rotation.integ.snapshot/manifest.json
@@ -1,5 +1,5 @@
 {
-  "version": "17.0.0",
+  "version": "18.0.0",
   "artifacts": {
     "Tree": {
       "type": "cdk:tree",
@@ -57,10 +57,19 @@
             "data": "LambdaD247545B"
           }
         ],
-        "/cdk-integ-secret-lambda-rotation/Lambda/InvokeServicePrincipal(secretsmanager.amazonaws.com)": [
+        "/cdk-integ-secret-lambda-rotation/Lambda/InvokeN0--a2GKfZP0JmDqDE--Vhhu6+A0TUv3NyNbk4YM+FKNc=": [
           {
             "type": "aws:cdk:logicalId",
-            "data": "LambdaInvokeServicePrincipalsecretsmanageramazonawscomB927629E"
+            "data": "LambdaInvokeN0a2GKfZP0JmDqDEVhhu6A0TUv3NyNbk4YMFKNc69846677"
+          }
+        ],
+        "LambdaInvokeServicePrincipalsecretsmanageramazonawscomB927629E": [
+          {
+            "type": "aws:cdk:logicalId",
+            "data": "LambdaInvokeServicePrincipalsecretsmanageramazonawscomB927629E",
+            "trace": [
+              "!!DESTRUCTIVE_CHANGES: WILL_DESTROY"
+            ]
           }
         ]
       },
diff --git a/packages/@aws-cdk/aws-secretsmanager/test/lambda-rotation.integ.snapshot/tree.json b/packages/@aws-cdk/aws-secretsmanager/test/lambda-rotation.integ.snapshot/tree.json
index 5904e23ee55a4..ef1855cbd73a1 100644
--- a/packages/@aws-cdk/aws-secretsmanager/test/lambda-rotation.integ.snapshot/tree.json
+++ b/packages/@aws-cdk/aws-secretsmanager/test/lambda-rotation.integ.snapshot/tree.json
@@ -394,9 +394,9 @@
                   "version": "0.0.0"
                 }
               },
-              "InvokeServicePrincipal(secretsmanager.amazonaws.com)": {
-                "id": "InvokeServicePrincipal(secretsmanager.amazonaws.com)",
-                "path": "cdk-integ-secret-lambda-rotation/Lambda/InvokeServicePrincipal(secretsmanager.amazonaws.com)",
+              "InvokeN0--a2GKfZP0JmDqDE--Vhhu6+A0TUv3NyNbk4YM+FKNc=": {
+                "id": "InvokeN0--a2GKfZP0JmDqDE--Vhhu6+A0TUv3NyNbk4YM+FKNc=",
+                "path": "cdk-integ-secret-lambda-rotation/Lambda/InvokeN0--a2GKfZP0JmDqDE--Vhhu6+A0TUv3NyNbk4YM+FKNc=",
                 "attributes": {
                   "aws:cdk:cloudformation:type": "AWS::Lambda::Permission",
                   "aws:cdk:cloudformation:props": {