diff --git a/.projen/deps.json b/.projen/deps.json
index 6ef161cbf..82a70ce8f 100644
--- a/.projen/deps.json
+++ b/.projen/deps.json
@@ -39,6 +39,10 @@
       "name": "@smithy/types",
       "type": "build"
     },
+    {
+      "name": "@smithy/util-retry",
+      "type": "build"
+    },
     {
       "name": "@smithy/util-stream",
       "type": "build"
diff --git a/.projen/tasks.json b/.projen/tasks.json
index 66abcb2f8..908d122fd 100644
--- a/.projen/tasks.json
+++ b/.projen/tasks.json
@@ -1201,13 +1201,13 @@
       },
       "steps": [
         {
-          "exec": "npx npm-check-updates@16 --upgrade --target=minor --peer --dep=dev --filter=@aws-sdk/client-codeartifact,@aws-sdk/client-s3,@aws-sdk/client-sfn,@jsii/spec,@octokit/rest,@smithy/types,@smithy/util-stream,@types/aws-lambda,@types/fs-extra,@types/jest,@types/markdown-it,@types/markdown-it-emoji,@types/semver,@types/streamx,@types/tar-stream,@types/tough-cookie,@types/uuid,async-sema,aws-embedded-metrics,aws-sdk,aws-sdk-client-mock,aws-sdk-client-mock-jest,aws-sdk-mock,aws-xray-sdk-core,case,cdk-dia,cdk-watchful,cdklabs-projen-project-types,chalk,construct-hub-webapp,dotenv,esbuild,eslint-config-prettier,eslint-import-resolver-typescript,eslint-plugin-import,eslint-plugin-prettier,feed,fs-extra,glob,got,jest,jsii-diff,jsii-pacmak,JSONStream,markdown-it,markdown-it-emoji,nock,normalize-registry-metadata,prettier,projen,semver,spdx-license-list,streamcount,streamx,tar-stream,ts-node,uuid,yaml"
+          "exec": "npx npm-check-updates@16 --upgrade --target=minor --peer --dep=dev --filter=@aws-sdk/client-codeartifact,@aws-sdk/client-s3,@aws-sdk/client-sfn,@jsii/spec,@octokit/rest,@smithy/types,@smithy/util-retry,@smithy/util-stream,@types/aws-lambda,@types/fs-extra,@types/jest,@types/markdown-it,@types/markdown-it-emoji,@types/semver,@types/streamx,@types/tar-stream,@types/tough-cookie,@types/uuid,async-sema,aws-embedded-metrics,aws-sdk,aws-sdk-client-mock,aws-sdk-client-mock-jest,aws-sdk-mock,aws-xray-sdk-core,case,cdk-dia,cdk-watchful,cdklabs-projen-project-types,chalk,construct-hub-webapp,dotenv,esbuild,eslint-config-prettier,eslint-import-resolver-typescript,eslint-plugin-import,eslint-plugin-prettier,feed,fs-extra,glob,got,jest,jsii-diff,jsii-pacmak,JSONStream,markdown-it,markdown-it-emoji,nock,normalize-registry-metadata,prettier,projen,semver,spdx-license-list,streamcount,streamx,tar-stream,ts-node,uuid,yaml"
         },
         {
           "exec": "yarn install --check-files"
         },
         {
-          "exec": "yarn upgrade @aws-cdk/aws-servicecatalogappregistry-alpha @aws-cdk/integ-runner @aws-cdk/integ-tests-alpha @aws-sdk/client-codeartifact @aws-sdk/client-s3 @aws-sdk/client-sfn @jsii/spec @octokit/rest @smithy/types @smithy/util-stream @types/aws-lambda @types/fs-extra @types/jest @types/markdown-it @types/markdown-it-emoji @types/node @types/semver @types/streamx @types/tar-stream @types/tough-cookie @types/uuid @typescript-eslint/eslint-plugin @typescript-eslint/parser async-sema aws-cdk-lib aws-cdk aws-embedded-metrics aws-sdk aws-sdk-client-mock aws-sdk-client-mock-jest aws-sdk-mock aws-xray-sdk-core case cdk-dia cdk-watchful cdklabs-projen-project-types chalk commit-and-tag-version construct-hub-webapp dotenv esbuild eslint-config-prettier eslint-import-resolver-typescript eslint-plugin-import eslint-plugin-prettier eslint feed fs-extra glob got jest jest-junit jsii-diff jsii-docgen jsii-pacmak jsii-rosetta jsii JSONStream markdown-it markdown-it-emoji nock normalize-registry-metadata prettier projen semver spdx-license-list streamcount streamx tar-stream ts-node typescript uuid yaml"
+          "exec": "yarn upgrade @aws-cdk/aws-servicecatalogappregistry-alpha @aws-cdk/integ-runner @aws-cdk/integ-tests-alpha @aws-sdk/client-codeartifact @aws-sdk/client-s3 @aws-sdk/client-sfn @jsii/spec @octokit/rest @smithy/types @smithy/util-retry @smithy/util-stream @types/aws-lambda @types/fs-extra @types/jest @types/markdown-it @types/markdown-it-emoji @types/node @types/semver @types/streamx @types/tar-stream @types/tough-cookie @types/uuid @typescript-eslint/eslint-plugin @typescript-eslint/parser async-sema aws-cdk-lib aws-cdk aws-embedded-metrics aws-sdk aws-sdk-client-mock aws-sdk-client-mock-jest aws-sdk-mock aws-xray-sdk-core case cdk-dia cdk-watchful cdklabs-projen-project-types chalk commit-and-tag-version construct-hub-webapp dotenv esbuild eslint-config-prettier eslint-import-resolver-typescript eslint-plugin-import eslint-plugin-prettier eslint feed fs-extra glob got jest jest-junit jsii-diff jsii-docgen jsii-pacmak jsii-rosetta jsii JSONStream markdown-it markdown-it-emoji nock normalize-registry-metadata prettier projen semver spdx-license-list streamcount streamx tar-stream ts-node typescript uuid yaml"
         },
         {
           "exec": "npx projen"
diff --git a/.projenrc.ts b/.projenrc.ts
index 1f0c90ab4..af9123401 100644
--- a/.projenrc.ts
+++ b/.projenrc.ts
@@ -50,6 +50,7 @@ const project = new CdklabsConstructLibrary({
     '@aws-sdk/client-codeartifact',
     '@aws-sdk/client-s3',
     '@smithy/types',
+    '@smithy/util-retry',
     '@smithy/util-stream',
     'async-sema',
     'aws-embedded-metrics',
diff --git a/package.json b/package.json
index 4b3253218..75c4f0e47 100644
--- a/package.json
+++ b/package.json
@@ -121,6 +121,7 @@
     "@jsii/spec": "^1.103.1",
     "@octokit/rest": "^19.0.13",
     "@smithy/types": "^3.3.0",
+    "@smithy/util-retry": "^3.0.4",
     "@smithy/util-stream": "^3.1.4",
     "@types/aws-lambda": "^8.10.145",
     "@types/fs-extra": "^11.0.4",
diff --git a/src/__tests__/__snapshots__/construct-hub.test.ts.snap b/src/__tests__/__snapshots__/construct-hub.test.ts.snap
index 460ffd003..2ea4c431f 100644
--- a/src/__tests__/__snapshots__/construct-hub.test.ts.snap
+++ b/src/__tests__/__snapshots__/construct-hub.test.ts.snap
@@ -2210,7 +2210,7 @@ Direct link to the function: /lambda/home#/functions/",
           "S3Bucket": {
             "Fn::Sub": "cdk-hnb659fds-assets-\${AWS::AccountId}-\${AWS::Region}",
           },
-          "S3Key": "92c30ddb1baaf0771dac0f79d4c3b1a6984baf8eac73e12cb0ab04f3f22fd096.zip",
+          "S3Key": "405dc475090f08c495a802305808b248fba97800ffd9705fc071d3940e869dea.zip",
         },
         "Description": "[ConstructHub/Ingestion] Ingests new package versions into the Construct Hub",
         "Environment": {
@@ -6802,10 +6802,18 @@ Warning: messages that resulted in a failed exectuion will NOT be in the DLQ!",
                 "Name": "AWS_EMF_ENVIRONMENT",
                 "Value": "Local",
               },
+              {
+                "Name": "MAX_CONCURRENT_S3_REQUESTS",
+                "Value": "16",
+              },
+              {
+                "Name": "MAX_RETRIES_S3_REQUESTS",
+                "Value": "12",
+              },
             ],
             "Essential": true,
             "Image": {
-              "Fn::Sub": "\${AWS::AccountId}.dkr.ecr.\${AWS::Region}.\${AWS::URLSuffix}/cdk-hnb659fds-container-assets-\${AWS::AccountId}-\${AWS::Region}:163c30075527137d291e3aef3865f2d7fabc82baf8e77bfcba58e32d2ce57564",
+              "Fn::Sub": "\${AWS::AccountId}.dkr.ecr.\${AWS::Region}.\${AWS::URLSuffix}/cdk-hnb659fds-container-assets-\${AWS::AccountId}-\${AWS::Region}:94f2518f19be80aed25d2146b42522cce8c3b71210c12d3f8b9eeef608433e8b",
             },
             "LogConfiguration": {
               "LogDriver": "awslogs",
@@ -15030,7 +15038,7 @@ Direct link to the function: /lambda/home#/functions/",
           "S3Bucket": {
             "Fn::Sub": "cdk-hnb659fds-assets-\${AWS::AccountId}-\${AWS::Region}",
           },
-          "S3Key": "92c30ddb1baaf0771dac0f79d4c3b1a6984baf8eac73e12cb0ab04f3f22fd096.zip",
+          "S3Key": "405dc475090f08c495a802305808b248fba97800ffd9705fc071d3940e869dea.zip",
         },
         "Description": "[ConstructHub/Ingestion] Ingests new package versions into the Construct Hub",
         "Environment": {
@@ -19720,6 +19728,14 @@ Warning: messages that resulted in a failed exectuion will NOT be in the DLQ!",
                 "Name": "AWS_EMF_ENVIRONMENT",
                 "Value": "Local",
               },
+              {
+                "Name": "MAX_CONCURRENT_S3_REQUESTS",
+                "Value": "16",
+              },
+              {
+                "Name": "MAX_RETRIES_S3_REQUESTS",
+                "Value": "12",
+              },
               {
                 "Name": "CODE_ARTIFACT_DOMAIN_NAME",
                 "Value": {
@@ -19750,7 +19766,7 @@ Warning: messages that resulted in a failed exectuion will NOT be in the DLQ!",
             ],
             "Essential": true,
             "Image": {
-              "Fn::Sub": "\${AWS::AccountId}.dkr.ecr.\${AWS::Region}.\${AWS::URLSuffix}/cdk-hnb659fds-container-assets-\${AWS::AccountId}-\${AWS::Region}:163c30075527137d291e3aef3865f2d7fabc82baf8e77bfcba58e32d2ce57564",
+              "Fn::Sub": "\${AWS::AccountId}.dkr.ecr.\${AWS::Region}.\${AWS::URLSuffix}/cdk-hnb659fds-container-assets-\${AWS::AccountId}-\${AWS::Region}:94f2518f19be80aed25d2146b42522cce8c3b71210c12d3f8b9eeef608433e8b",
             },
             "LogConfiguration": {
               "LogDriver": "awslogs",
@@ -27764,7 +27780,7 @@ Direct link to the function: /lambda/home#/functions/",
           "S3Bucket": {
             "Fn::Sub": "cdk-hnb659fds-assets-\${AWS::AccountId}-\${AWS::Region}",
           },
-          "S3Key": "92c30ddb1baaf0771dac0f79d4c3b1a6984baf8eac73e12cb0ab04f3f22fd096.zip",
+          "S3Key": "405dc475090f08c495a802305808b248fba97800ffd9705fc071d3940e869dea.zip",
         },
         "Description": "[ConstructHub/Ingestion] Ingests new package versions into the Construct Hub",
         "Environment": {
@@ -32356,10 +32372,18 @@ Warning: messages that resulted in a failed exectuion will NOT be in the DLQ!",
                 "Name": "AWS_EMF_ENVIRONMENT",
                 "Value": "Local",
               },
+              {
+                "Name": "MAX_CONCURRENT_S3_REQUESTS",
+                "Value": "16",
+              },
+              {
+                "Name": "MAX_RETRIES_S3_REQUESTS",
+                "Value": "12",
+              },
             ],
             "Essential": true,
             "Image": {
-              "Fn::Sub": "\${AWS::AccountId}.dkr.ecr.\${AWS::Region}.\${AWS::URLSuffix}/cdk-hnb659fds-container-assets-\${AWS::AccountId}-\${AWS::Region}:163c30075527137d291e3aef3865f2d7fabc82baf8e77bfcba58e32d2ce57564",
+              "Fn::Sub": "\${AWS::AccountId}.dkr.ecr.\${AWS::Region}.\${AWS::URLSuffix}/cdk-hnb659fds-container-assets-\${AWS::AccountId}-\${AWS::Region}:94f2518f19be80aed25d2146b42522cce8c3b71210c12d3f8b9eeef608433e8b",
             },
             "LogConfiguration": {
               "LogDriver": "awslogs",
@@ -40454,7 +40478,7 @@ Direct link to the function: /lambda/home#/functions/",
           "S3Bucket": {
             "Fn::Sub": "cdk-hnb659fds-assets-\${AWS::AccountId}-\${AWS::Region}",
           },
-          "S3Key": "92c30ddb1baaf0771dac0f79d4c3b1a6984baf8eac73e12cb0ab04f3f22fd096.zip",
+          "S3Key": "405dc475090f08c495a802305808b248fba97800ffd9705fc071d3940e869dea.zip",
         },
         "Description": "[ConstructHub/Ingestion] Ingests new package versions into the Construct Hub",
         "Environment": {
@@ -45068,10 +45092,18 @@ Warning: messages that resulted in a failed exectuion will NOT be in the DLQ!",
                 "Name": "AWS_EMF_ENVIRONMENT",
                 "Value": "Local",
               },
+              {
+                "Name": "MAX_CONCURRENT_S3_REQUESTS",
+                "Value": "16",
+              },
+              {
+                "Name": "MAX_RETRIES_S3_REQUESTS",
+                "Value": "12",
+              },
             ],
             "Essential": true,
             "Image": {
-              "Fn::Sub": "\${AWS::AccountId}.dkr.ecr.\${AWS::Region}.\${AWS::URLSuffix}/cdk-hnb659fds-container-assets-\${AWS::AccountId}-\${AWS::Region}:163c30075527137d291e3aef3865f2d7fabc82baf8e77bfcba58e32d2ce57564",
+              "Fn::Sub": "\${AWS::AccountId}.dkr.ecr.\${AWS::Region}.\${AWS::URLSuffix}/cdk-hnb659fds-container-assets-\${AWS::AccountId}-\${AWS::Region}:94f2518f19be80aed25d2146b42522cce8c3b71210c12d3f8b9eeef608433e8b",
             },
             "LogConfiguration": {
               "LogDriver": "awslogs",
@@ -53353,7 +53385,7 @@ Direct link to the function: /lambda/home#/functions/",
           "S3Bucket": {
             "Fn::Sub": "cdk-hnb659fds-assets-\${AWS::AccountId}-\${AWS::Region}",
           },
-          "S3Key": "92c30ddb1baaf0771dac0f79d4c3b1a6984baf8eac73e12cb0ab04f3f22fd096.zip",
+          "S3Key": "405dc475090f08c495a802305808b248fba97800ffd9705fc071d3940e869dea.zip",
         },
         "Description": "[ConstructHub/Ingestion] Ingests new package versions into the Construct Hub",
         "Environment": {
@@ -57699,10 +57731,18 @@ Warning: messages that resulted in a failed exectuion will NOT be in the DLQ!",
                 "Name": "AWS_EMF_ENVIRONMENT",
                 "Value": "Local",
               },
+              {
+                "Name": "MAX_CONCURRENT_S3_REQUESTS",
+                "Value": "16",
+              },
+              {
+                "Name": "MAX_RETRIES_S3_REQUESTS",
+                "Value": "12",
+              },
             ],
             "Essential": true,
             "Image": {
-              "Fn::Sub": "\${AWS::AccountId}.dkr.ecr.\${AWS::Region}.\${AWS::URLSuffix}/cdk-hnb659fds-container-assets-\${AWS::AccountId}-\${AWS::Region}:163c30075527137d291e3aef3865f2d7fabc82baf8e77bfcba58e32d2ce57564",
+              "Fn::Sub": "\${AWS::AccountId}.dkr.ecr.\${AWS::Region}.\${AWS::URLSuffix}/cdk-hnb659fds-container-assets-\${AWS::AccountId}-\${AWS::Region}:94f2518f19be80aed25d2146b42522cce8c3b71210c12d3f8b9eeef608433e8b",
             },
             "LogConfiguration": {
               "LogDriver": "awslogs",
diff --git a/src/__tests__/backend/transliterator/__snapshots__/index.test.ts.snap b/src/__tests__/backend/transliterator/__snapshots__/index.test.ts.snap
index 482f246de..5ede42fda 100644
--- a/src/__tests__/backend/transliterator/__snapshots__/index.test.ts.snap
+++ b/src/__tests__/backend/transliterator/__snapshots__/index.test.ts.snap
@@ -88,6 +88,14 @@ exports[`CodeArtifact repository 1`] = `
                 "Name": "AWS_EMF_ENVIRONMENT",
                 "Value": "Local",
               },
+              {
+                "Name": "MAX_CONCURRENT_S3_REQUESTS",
+                "Value": "16",
+              },
+              {
+                "Name": "MAX_RETRIES_S3_REQUESTS",
+                "Value": "12",
+              },
               {
                 "Name": "CODE_ARTIFACT_DOMAIN_NAME",
                 "Value": {
@@ -118,7 +126,7 @@ exports[`CodeArtifact repository 1`] = `
             ],
             "Essential": true,
             "Image": {
-              "Fn::Sub": "\${AWS::AccountId}.dkr.ecr.\${AWS::Region}.\${AWS::URLSuffix}/cdk-hnb659fds-container-assets-\${AWS::AccountId}-\${AWS::Region}:163c30075527137d291e3aef3865f2d7fabc82baf8e77bfcba58e32d2ce57564",
+              "Fn::Sub": "\${AWS::AccountId}.dkr.ecr.\${AWS::Region}.\${AWS::URLSuffix}/cdk-hnb659fds-container-assets-\${AWS::AccountId}-\${AWS::Region}:94f2518f19be80aed25d2146b42522cce8c3b71210c12d3f8b9eeef608433e8b",
             },
             "LogConfiguration": {
               "LogDriver": "awslogs",
@@ -2399,6 +2407,14 @@ exports[`VPC Endpoints 1`] = `
                 "Name": "AWS_EMF_ENVIRONMENT",
                 "Value": "Local",
               },
+              {
+                "Name": "MAX_CONCURRENT_S3_REQUESTS",
+                "Value": "16",
+              },
+              {
+                "Name": "MAX_RETRIES_S3_REQUESTS",
+                "Value": "12",
+              },
               {
                 "Name": "CODE_ARTIFACT_API_ENDPOINT",
                 "Value": {
@@ -2426,7 +2442,7 @@ exports[`VPC Endpoints 1`] = `
             ],
             "Essential": true,
             "Image": {
-              "Fn::Sub": "\${AWS::AccountId}.dkr.ecr.\${AWS::Region}.\${AWS::URLSuffix}/cdk-hnb659fds-container-assets-\${AWS::AccountId}-\${AWS::Region}:163c30075527137d291e3aef3865f2d7fabc82baf8e77bfcba58e32d2ce57564",
+              "Fn::Sub": "\${AWS::AccountId}.dkr.ecr.\${AWS::Region}.\${AWS::URLSuffix}/cdk-hnb659fds-container-assets-\${AWS::AccountId}-\${AWS::Region}:94f2518f19be80aed25d2146b42522cce8c3b71210c12d3f8b9eeef608433e8b",
             },
             "LogConfiguration": {
               "LogDriver": "awslogs",
@@ -4731,6 +4747,14 @@ exports[`VPC Endpoints and CodeArtifact repository 1`] = `
                 "Name": "AWS_EMF_ENVIRONMENT",
                 "Value": "Local",
               },
+              {
+                "Name": "MAX_CONCURRENT_S3_REQUESTS",
+                "Value": "16",
+              },
+              {
+                "Name": "MAX_RETRIES_S3_REQUESTS",
+                "Value": "12",
+              },
               {
                 "Name": "CODE_ARTIFACT_API_ENDPOINT",
                 "Value": {
@@ -4785,7 +4809,7 @@ exports[`VPC Endpoints and CodeArtifact repository 1`] = `
             ],
             "Essential": true,
             "Image": {
-              "Fn::Sub": "\${AWS::AccountId}.dkr.ecr.\${AWS::Region}.\${AWS::URLSuffix}/cdk-hnb659fds-container-assets-\${AWS::AccountId}-\${AWS::Region}:163c30075527137d291e3aef3865f2d7fabc82baf8e77bfcba58e32d2ce57564",
+              "Fn::Sub": "\${AWS::AccountId}.dkr.ecr.\${AWS::Region}.\${AWS::URLSuffix}/cdk-hnb659fds-container-assets-\${AWS::AccountId}-\${AWS::Region}:94f2518f19be80aed25d2146b42522cce8c3b71210c12d3f8b9eeef608433e8b",
             },
             "LogConfiguration": {
               "LogDriver": "awslogs",
@@ -7086,10 +7110,18 @@ exports[`basic use 1`] = `
                 "Name": "AWS_EMF_ENVIRONMENT",
                 "Value": "Local",
               },
+              {
+                "Name": "MAX_CONCURRENT_S3_REQUESTS",
+                "Value": "16",
+              },
+              {
+                "Name": "MAX_RETRIES_S3_REQUESTS",
+                "Value": "12",
+              },
             ],
             "Essential": true,
             "Image": {
-              "Fn::Sub": "\${AWS::AccountId}.dkr.ecr.\${AWS::Region}.\${AWS::URLSuffix}/cdk-hnb659fds-container-assets-\${AWS::AccountId}-\${AWS::Region}:163c30075527137d291e3aef3865f2d7fabc82baf8e77bfcba58e32d2ce57564",
+              "Fn::Sub": "\${AWS::AccountId}.dkr.ecr.\${AWS::Region}.\${AWS::URLSuffix}/cdk-hnb659fds-container-assets-\${AWS::AccountId}-\${AWS::Region}:94f2518f19be80aed25d2146b42522cce8c3b71210c12d3f8b9eeef608433e8b",
             },
             "LogConfiguration": {
               "LogDriver": "awslogs",
diff --git a/src/__tests__/backend/transliterator/index.test.ts b/src/__tests__/backend/transliterator/index.test.ts
index be766544c..d1417caaa 100644
--- a/src/__tests__/backend/transliterator/index.test.ts
+++ b/src/__tests__/backend/transliterator/index.test.ts
@@ -58,6 +58,14 @@ test('CodeArtifact repository', () => {
         Environment: stack.resolve([
           { Name: 'HEADER_SPAN', Value: 'true' },
           { Name: 'AWS_EMF_ENVIRONMENT', Value: 'Local' },
+          {
+            Name: 'MAX_CONCURRENT_S3_REQUESTS',
+            Value: '16',
+          },
+          {
+            Name: 'MAX_RETRIES_S3_REQUESTS',
+            Value: '12',
+          },
           {
             Name: 'CODE_ARTIFACT_DOMAIN_NAME',
             Value: codeArtifact.repositoryDomainName,
@@ -138,6 +146,14 @@ test('VPC Endpoints', () => {
         Environment: stack.resolve([
           { Name: 'HEADER_SPAN', Value: 'true' },
           { Name: 'AWS_EMF_ENVIRONMENT', Value: 'Local' },
+          {
+            Name: 'MAX_CONCURRENT_S3_REQUESTS',
+            Value: '16',
+          },
+          {
+            Name: 'MAX_RETRIES_S3_REQUESTS',
+            Value: '12',
+          },
           {
             Name: 'CODE_ARTIFACT_API_ENDPOINT',
             Value: Fn.select(
@@ -214,6 +230,14 @@ test('VPC Endpoints and CodeArtifact repository', () => {
         Environment: stack.resolve([
           { Name: 'HEADER_SPAN', Value: 'true' },
           { Name: 'AWS_EMF_ENVIRONMENT', Value: 'Local' },
+          {
+            Name: 'MAX_CONCURRENT_S3_REQUESTS',
+            Value: '16',
+          },
+          {
+            Name: 'MAX_RETRIES_S3_REQUESTS',
+            Value: '12',
+          },
           {
             Name: 'CODE_ARTIFACT_API_ENDPOINT',
             Value: Fn.select(
diff --git a/src/__tests__/devapp/__snapshots__/snapshot.test.ts.snap b/src/__tests__/devapp/__snapshots__/snapshot.test.ts.snap
index 7877f8b97..05065ec9f 100644
--- a/src/__tests__/devapp/__snapshots__/snapshot.test.ts.snap
+++ b/src/__tests__/devapp/__snapshots__/snapshot.test.ts.snap
@@ -2665,7 +2665,7 @@ Direct link to the function: /lambda/home#/functions/",
           "S3Bucket": {
             "Fn::Sub": "cdk-hnb659fds-assets-\${AWS::AccountId}-\${AWS::Region}",
           },
-          "S3Key": "92c30ddb1baaf0771dac0f79d4c3b1a6984baf8eac73e12cb0ab04f3f22fd096.zip",
+          "S3Key": "405dc475090f08c495a802305808b248fba97800ffd9705fc071d3940e869dea.zip",
         },
         "Description": "[ConstructHub/Ingestion] Ingests new package versions into the Construct Hub",
         "Environment": {
@@ -7017,6 +7017,14 @@ Warning: messages that resulted in a failed exectuion will NOT be in the DLQ!",
                 "Name": "AWS_EMF_ENVIRONMENT",
                 "Value": "Local",
               },
+              {
+                "Name": "MAX_CONCURRENT_S3_REQUESTS",
+                "Value": "16",
+              },
+              {
+                "Name": "MAX_RETRIES_S3_REQUESTS",
+                "Value": "12",
+              },
               {
                 "Name": "CODE_ARTIFACT_API_ENDPOINT",
                 "Value": {
@@ -7071,7 +7079,7 @@ Warning: messages that resulted in a failed exectuion will NOT be in the DLQ!",
             ],
             "Essential": true,
             "Image": {
-              "Fn::Sub": "\${AWS::AccountId}.dkr.ecr.\${AWS::Region}.\${AWS::URLSuffix}/cdk-hnb659fds-container-assets-\${AWS::AccountId}-\${AWS::Region}:163c30075527137d291e3aef3865f2d7fabc82baf8e77bfcba58e32d2ce57564",
+              "Fn::Sub": "\${AWS::AccountId}.dkr.ecr.\${AWS::Region}.\${AWS::URLSuffix}/cdk-hnb659fds-container-assets-\${AWS::AccountId}-\${AWS::Region}:94f2518f19be80aed25d2146b42522cce8c3b71210c12d3f8b9eeef608433e8b",
             },
             "LogConfiguration": {
               "LogDriver": "awslogs",
diff --git a/src/backend/transliterator/index.ts b/src/backend/transliterator/index.ts
index a1822c505..aff779ed4 100644
--- a/src/backend/transliterator/index.ts
+++ b/src/backend/transliterator/index.ts
@@ -127,11 +127,15 @@ export class Transliterator extends Construct {
       : props.bucket;
 
     const environment: Record<string, string> = {
-      // temporaty hack to generate construct-hub compliant markdown.
+      // temporary hack to generate construct-hub compliant markdown.
       // see https://github.com/cdklabs/jsii-docgen/blob/master/src/docgen/render/markdown.ts#L172
       HEADER_SPAN: 'true',
       // Set embedded metrics format environment to "Local", to have a consistent experience.
       AWS_EMF_ENVIRONMENT: 'Local',
+      // Limit the number of concurrent S3 requests
+      MAX_CONCURRENT_S3_REQUESTS: '16',
+      // The maximal number of retries for throttled S3 requests
+      MAX_RETRIES_S3_REQUESTS: '12',
     };
     if (props.vpcEndpoints?.codeArtifactApi) {
       // Those are returned as an array of HOSTED_ZONE_ID:DNS_NAME... We care
diff --git a/src/backend/transliterator/transliterator.ecstask.ts b/src/backend/transliterator/transliterator.ecstask.ts
index 574449f68..047dba4d2 100644
--- a/src/backend/transliterator/transliterator.ecstask.ts
+++ b/src/backend/transliterator/transliterator.ecstask.ts
@@ -13,6 +13,7 @@ import {
 } from '@aws-sdk/client-s3';
 import { Assembly } from '@jsii/spec';
 import { StreamingBlobPayloadInputTypes } from '@smithy/types';
+import { AdaptiveRetryStrategy } from '@smithy/util-retry';
 import { Sema } from 'async-sema';
 import { metricScope, Unit } from 'aws-embedded-metrics';
 import * as docgen from 'jsii-docgen';
@@ -35,10 +36,16 @@ const S3_SEMAPHORE = new Sema(
   parseInt(process.env.MAX_CONCURRENT_S3_REQUESTS ?? '16', 10)
 );
 
+const MAX_RETRIES_S3_REQUESTS = parseInt(
+  process.env.MAX_RETRIES_S3_REQUESTS ?? '12',
+  10
+);
 const S3_CLIENT = new S3Client({
   // https://docs.aws.amazon.com/sdkref/latest/guide/feature-retry-behavior.html#standardvsadaptive
   // This works because S3 throttles requests based on prefix
-  retryMode: 'ADAPTIVE',
+  retryStrategy: new AdaptiveRetryStrategy(
+    async () => MAX_RETRIES_S3_REQUESTS /* maxAttempts */
+  ),
 });
 
 /**
diff --git a/test/integ.transliterator.ecstask.ts.snapshot/TransliteratorEcsTaskInteg.assets.json b/test/integ.transliterator.ecstask.ts.snapshot/TransliteratorEcsTaskInteg.assets.json
index 2b5b7e228..2353ac33b 100644
--- a/test/integ.transliterator.ecstask.ts.snapshot/TransliteratorEcsTaskInteg.assets.json
+++ b/test/integ.transliterator.ecstask.ts.snapshot/TransliteratorEcsTaskInteg.assets.json
@@ -40,7 +40,7 @@
         }
       }
     },
-    "5734d7ab060d267f335136d0ba9378f40a5698385392dee3bdcd54caf075dadc": {
+    "d629183b3b5a048fa164c7601cf0c01fe6a87cc1b7c2535a08a8413e2708ab95": {
       "source": {
         "path": "TransliteratorEcsTaskInteg.template.json",
         "packaging": "file"
@@ -48,22 +48,22 @@
       "destinations": {
         "current_account-current_region": {
           "bucketName": "cdk-hnb659fds-assets-${AWS::AccountId}-${AWS::Region}",
-          "objectKey": "5734d7ab060d267f335136d0ba9378f40a5698385392dee3bdcd54caf075dadc.json",
+          "objectKey": "d629183b3b5a048fa164c7601cf0c01fe6a87cc1b7c2535a08a8413e2708ab95.json",
           "assumeRoleArn": "arn:${AWS::Partition}:iam::${AWS::AccountId}:role/cdk-hnb659fds-file-publishing-role-${AWS::AccountId}-${AWS::Region}"
         }
       }
     }
   },
   "dockerImages": {
-    "163c30075527137d291e3aef3865f2d7fabc82baf8e77bfcba58e32d2ce57564": {
+    "94f2518f19be80aed25d2146b42522cce8c3b71210c12d3f8b9eeef608433e8b": {
       "source": {
-        "directory": "asset.163c30075527137d291e3aef3865f2d7fabc82baf8e77bfcba58e32d2ce57564.bundle",
+        "directory": "asset.94f2518f19be80aed25d2146b42522cce8c3b71210c12d3f8b9eeef608433e8b.bundle",
         "platform": "linux/arm64"
       },
       "destinations": {
         "current_account-current_region": {
           "repositoryName": "cdk-hnb659fds-container-assets-${AWS::AccountId}-${AWS::Region}",
-          "imageTag": "163c30075527137d291e3aef3865f2d7fabc82baf8e77bfcba58e32d2ce57564",
+          "imageTag": "94f2518f19be80aed25d2146b42522cce8c3b71210c12d3f8b9eeef608433e8b",
           "assumeRoleArn": "arn:${AWS::Partition}:iam::${AWS::AccountId}:role/cdk-hnb659fds-image-publishing-role-${AWS::AccountId}-${AWS::Region}"
         }
       }
diff --git a/test/integ.transliterator.ecstask.ts.snapshot/TransliteratorEcsTaskInteg.template.json b/test/integ.transliterator.ecstask.ts.snapshot/TransliteratorEcsTaskInteg.template.json
index 4192459ba..5eafbf72f 100644
--- a/test/integ.transliterator.ecstask.ts.snapshot/TransliteratorEcsTaskInteg.template.json
+++ b/test/integ.transliterator.ecstask.ts.snapshot/TransliteratorEcsTaskInteg.template.json
@@ -1481,11 +1481,19 @@
        {
         "Name": "AWS_EMF_ENVIRONMENT",
         "Value": "Local"
+       },
+       {
+        "Name": "MAX_CONCURRENT_S3_REQUESTS",
+        "Value": "16"
+       },
+       {
+        "Name": "MAX_RETRIES_S3_REQUESTS",
+        "Value": "12"
        }
       ],
       "Essential": true,
       "Image": {
-       "Fn::Sub": "${AWS::AccountId}.dkr.ecr.${AWS::Region}.${AWS::URLSuffix}/cdk-hnb659fds-container-assets-${AWS::AccountId}-${AWS::Region}:163c30075527137d291e3aef3865f2d7fabc82baf8e77bfcba58e32d2ce57564"
+       "Fn::Sub": "${AWS::AccountId}.dkr.ecr.${AWS::Region}.${AWS::URLSuffix}/cdk-hnb659fds-container-assets-${AWS::AccountId}-${AWS::Region}:94f2518f19be80aed25d2146b42522cce8c3b71210c12d3f8b9eeef608433e8b"
       },
       "LogConfiguration": {
        "LogDriver": "awslogs",
diff --git a/test/integ.transliterator.ecstask.ts.snapshot/manifest.json b/test/integ.transliterator.ecstask.ts.snapshot/manifest.json
index 83cdd520c..7d6abc450 100644
--- a/test/integ.transliterator.ecstask.ts.snapshot/manifest.json
+++ b/test/integ.transliterator.ecstask.ts.snapshot/manifest.json
@@ -18,7 +18,7 @@
         "validateOnSynth": false,
         "assumeRoleArn": "arn:${AWS::Partition}:iam::${AWS::AccountId}:role/cdk-hnb659fds-deploy-role-${AWS::AccountId}-${AWS::Region}",
         "cloudFormationExecutionRoleArn": "arn:${AWS::Partition}:iam::${AWS::AccountId}:role/cdk-hnb659fds-cfn-exec-role-${AWS::AccountId}-${AWS::Region}",
-        "stackTemplateAssetObjectUrl": "s3://cdk-hnb659fds-assets-${AWS::AccountId}-${AWS::Region}/5734d7ab060d267f335136d0ba9378f40a5698385392dee3bdcd54caf075dadc.json",
+        "stackTemplateAssetObjectUrl": "s3://cdk-hnb659fds-assets-${AWS::AccountId}-${AWS::Region}/d629183b3b5a048fa164c7601cf0c01fe6a87cc1b7c2535a08a8413e2708ab95.json",
         "requiresBootstrapStackVersion": 6,
         "bootstrapStackVersionSsmParameter": "/cdk-bootstrap/hnb659fds/version",
         "additionalDependencies": [
@@ -217,7 +217,10 @@
         "/TransliteratorEcsTaskInteg/Transliterator/TaskDefinition/Resource": [
           {
             "type": "aws:cdk:logicalId",
-            "data": "TransliteratorTaskDefinition16158D86"
+            "data": "TransliteratorTaskDefinition16158D86",
+            "trace": [
+              "!!DESTRUCTIVE_CHANGES: WILL_REPLACE"
+            ]
           }
         ],
         "/TransliteratorEcsTaskInteg/Transliterator/TaskDefinition/ExecutionRole/Resource": [
@@ -330,7 +333,7 @@
         "validateOnSynth": false,
         "assumeRoleArn": "arn:${AWS::Partition}:iam::${AWS::AccountId}:role/cdk-hnb659fds-deploy-role-${AWS::AccountId}-${AWS::Region}",
         "cloudFormationExecutionRoleArn": "arn:${AWS::Partition}:iam::${AWS::AccountId}:role/cdk-hnb659fds-cfn-exec-role-${AWS::AccountId}-${AWS::Region}",
-        "stackTemplateAssetObjectUrl": "s3://cdk-hnb659fds-assets-${AWS::AccountId}-${AWS::Region}/c58e15f764cc8151a7d2c4b0acf232e94fca93b829e20ef090a20cf5517bf58c.json",
+        "stackTemplateAssetObjectUrl": "s3://cdk-hnb659fds-assets-${AWS::AccountId}-${AWS::Region}/d1c573df1179c0a28edfc45dc8da18afec8fceb6ffcfd0bcaea00a1fde15e24a.json",
         "requiresBootstrapStackVersion": 6,
         "bootstrapStackVersionSsmParameter": "/cdk-bootstrap/hnb659fds/version",
         "additionalDependencies": [
diff --git a/test/integ.transliterator.ecstask.ts.snapshot/transliteratorintegDefaultTestDeployAssert109DC8B0.assets.json b/test/integ.transliterator.ecstask.ts.snapshot/transliteratorintegDefaultTestDeployAssert109DC8B0.assets.json
index 88d2c401a..9e43d2baa 100644
--- a/test/integ.transliterator.ecstask.ts.snapshot/transliteratorintegDefaultTestDeployAssert109DC8B0.assets.json
+++ b/test/integ.transliterator.ecstask.ts.snapshot/transliteratorintegDefaultTestDeployAssert109DC8B0.assets.json
@@ -14,7 +14,7 @@
         }
       }
     },
-    "c58e15f764cc8151a7d2c4b0acf232e94fca93b829e20ef090a20cf5517bf58c": {
+    "d1c573df1179c0a28edfc45dc8da18afec8fceb6ffcfd0bcaea00a1fde15e24a": {
       "source": {
         "path": "transliteratorintegDefaultTestDeployAssert109DC8B0.template.json",
         "packaging": "file"
@@ -22,7 +22,7 @@
       "destinations": {
         "current_account-current_region": {
           "bucketName": "cdk-hnb659fds-assets-${AWS::AccountId}-${AWS::Region}",
-          "objectKey": "c58e15f764cc8151a7d2c4b0acf232e94fca93b829e20ef090a20cf5517bf58c.json",
+          "objectKey": "d1c573df1179c0a28edfc45dc8da18afec8fceb6ffcfd0bcaea00a1fde15e24a.json",
           "assumeRoleArn": "arn:${AWS::Partition}:iam::${AWS::AccountId}:role/cdk-hnb659fds-file-publishing-role-${AWS::AccountId}-${AWS::Region}"
         }
       }
diff --git a/test/integ.transliterator.ecstask.ts.snapshot/transliteratorintegDefaultTestDeployAssert109DC8B0.template.json b/test/integ.transliterator.ecstask.ts.snapshot/transliteratorintegDefaultTestDeployAssert109DC8B0.template.json
index f8bf1fd0f..f4b5bd6db 100644
--- a/test/integ.transliterator.ecstask.ts.snapshot/transliteratorintegDefaultTestDeployAssert109DC8B0.template.json
+++ b/test/integ.transliterator.ecstask.ts.snapshot/transliteratorintegDefaultTestDeployAssert109DC8B0.template.json
@@ -41,7 +41,7 @@
     "outputPaths": [
      "executionArn"
     ],
-    "salt": "1725967583740"
+    "salt": "1725976481239"
    },
    "UpdateReplacePolicy": "Delete",
    "DeletionPolicy": "Delete"
@@ -158,7 +158,7 @@
      }
     },
     "flattenResponse": "false",
-    "salt": "1725967583741"
+    "salt": "1725976481241"
    },
    "UpdateReplacePolicy": "Delete",
    "DeletionPolicy": "Delete"
diff --git a/test/integ.transliterator.ecstask.ts.snapshot/tree.json b/test/integ.transliterator.ecstask.ts.snapshot/tree.json
index 0e7124fec..c26f3c042 100644
--- a/test/integ.transliterator.ecstask.ts.snapshot/tree.json
+++ b/test/integ.transliterator.ecstask.ts.snapshot/tree.json
@@ -1875,7 +1875,7 @@
                           {
                             "essential": true,
                             "image": {
-                              "Fn::Sub": "${AWS::AccountId}.dkr.ecr.${AWS::Region}.${AWS::URLSuffix}/cdk-hnb659fds-container-assets-${AWS::AccountId}-${AWS::Region}:163c30075527137d291e3aef3865f2d7fabc82baf8e77bfcba58e32d2ce57564"
+                              "Fn::Sub": "${AWS::AccountId}.dkr.ecr.${AWS::Region}.${AWS::URLSuffix}/cdk-hnb659fds-container-assets-${AWS::AccountId}-${AWS::Region}:94f2518f19be80aed25d2146b42522cce8c3b71210c12d3f8b9eeef608433e8b"
                             },
                             "name": "Resource",
                             "logConfiguration": {
@@ -1898,6 +1898,14 @@
                               {
                                 "name": "AWS_EMF_ENVIRONMENT",
                                 "value": "Local"
+                              },
+                              {
+                                "name": "MAX_CONCURRENT_S3_REQUESTS",
+                                "value": "16"
+                              },
+                              {
+                                "name": "MAX_RETRIES_S3_REQUESTS",
+                                "value": "12"
                               }
                             ]
                           }
diff --git a/yarn.lock b/yarn.lock
index 8842ca785..6044e64c8 100644
--- a/yarn.lock
+++ b/yarn.lock
@@ -2841,6 +2841,13 @@
   dependencies:
     "@smithy/types" "^3.3.0"
 
+"@smithy/service-error-classification@^3.0.4":
+  version "3.0.4"
+  resolved "https://registry.yarnpkg.com/@smithy/service-error-classification/-/service-error-classification-3.0.4.tgz#60e07b596b38d316aca453e06bfe33464c622fb5"
+  integrity sha512-KciDHHKFVTb9A1KlJHBt2F26PBaDtoE23uTZy5qRvPzHPqrooXFi6fmx98lJb3Jl38PuUTqIuCUmmY3pacuMBQ==
+  dependencies:
+    "@smithy/types" "^3.4.0"
+
 "@smithy/shared-ini-file-loader@^3.1.4":
   version "3.1.4"
   resolved "https://registry.yarnpkg.com/@smithy/shared-ini-file-loader/-/shared-ini-file-loader-3.1.4.tgz#7dceaf5a5307a2ee347ace8aba17312a1a3ede15"
@@ -3008,6 +3015,15 @@
     "@smithy/types" "^3.3.0"
     tslib "^2.6.2"
 
+"@smithy/util-retry@^3.0.4":
+  version "3.0.4"
+  resolved "https://registry.yarnpkg.com/@smithy/util-retry/-/util-retry-3.0.4.tgz#281de3f89458b5e3b86ca92937eb1212bcecf67f"
+  integrity sha512-JJr6g0tO1qO2tCQyK+n3J18r34ZpvatlFN5ULcLranFIBZPxqoivb77EPyNTVwTGMEvvq2qMnyjm4jMIxjdLFg==
+  dependencies:
+    "@smithy/service-error-classification" "^3.0.4"
+    "@smithy/types" "^3.4.0"
+    tslib "^2.6.2"
+
 "@smithy/util-stream@^3.1.3":
   version "3.1.3"
   resolved "https://registry.yarnpkg.com/@smithy/util-stream/-/util-stream-3.1.3.tgz#699ee2397cc1d474e46d2034039d5263812dca64"