diff --git a/.github/workflows/cdk-nag.yml b/.github/workflows/cdk-nag.yml
index 1bc47b8fb..4072b8119 100644
--- a/.github/workflows/cdk-nag.yml
+++ b/.github/workflows/cdk-nag.yml
@@ -23,4 +23,4 @@ jobs:
           node-version: ${{ matrix.node-version }}
       - run: |
           cd source/constructs && npm i --only=dev
-          npx cdk synth
+          npx cdk synth
\ No newline at end of file
diff --git a/.github/workflows/code-style-lint.yml b/.github/workflows/code-style-lint.yml
index 2c47471be..c9a117163 100644
--- a/.github/workflows/code-style-lint.yml
+++ b/.github/workflows/code-style-lint.yml
@@ -33,4 +33,4 @@ jobs:
           node-version: ${{ matrix.node-version }}
       - run: |
           cd source && npm i --only=dev
-          npx --y eslint . --ext .ts
+          npx --y eslint . --ext .ts
\ No newline at end of file
diff --git a/.github/workflows/codeql.yml b/.github/workflows/codeql.yml
index 8fab20972..1ecc1b03d 100644
--- a/.github/workflows/codeql.yml
+++ b/.github/workflows/codeql.yml
@@ -21,4 +21,4 @@ jobs:
       - uses: github/codeql-action/init@v2
         with:
             languages: ${{ matrix.language }}
-      - uses: github/codeql-action/analyze@v2
+      - uses: github/codeql-action/analyze@v2
\ No newline at end of file
diff --git a/.github/workflows/run-unit-test.yml b/.github/workflows/run-unit-test.yml
index 0d9661ca2..acb73c9b5 100644
--- a/.github/workflows/run-unit-test.yml
+++ b/.github/workflows/run-unit-test.yml
@@ -23,4 +23,4 @@ jobs:
           node-version: ${{ matrix.node-version }}
       - run: |
           cd deployment
-          chmod +x ./run-unit-tests.sh && DEBUG=true ./run-unit-tests.sh
+          chmod +x ./run-unit-tests.sh && DEBUG=true ./run-unit-tests.sh
\ No newline at end of file
diff --git a/deployment/run-unit-tests.sh b/deployment/run-unit-tests.sh
index 76d56a1af..43746bea4 100755
--- a/deployment/run-unit-tests.sh
+++ b/deployment/run-unit-tests.sh
@@ -53,6 +53,7 @@ declare -a lambda_packages=(
   "constructs"
   "image-handler"
   "custom-resource"
+  "solution-utils"
 )
 
 export overrideWarningsEnabled=false
diff --git a/source/image-handler/image-request.ts b/source/image-handler/image-request.ts
index f17b25e44..24c845689 100644
--- a/source/image-handler/image-request.ts
+++ b/source/image-handler/image-request.ts
@@ -18,6 +18,7 @@ import {
 } from "./lib";
 import { SecretProvider } from "./secret-provider";
 import { ThumborMapper } from "./thumbor-mapper";
+import { parseJson, generateRegExp } from "../solution-utils/helpers";
 
 type OriginalImageInfo = Partial<{
   contentType: string;
@@ -278,15 +279,18 @@ export class ImageRequest {
       if (requestType === RequestTypes.CUSTOM) {
         const { REWRITE_MATCH_PATTERN, REWRITE_SUBSTITUTION } = process.env;
 
-        if (typeof REWRITE_MATCH_PATTERN === "string") {
-          const patternStrings = REWRITE_MATCH_PATTERN.split("/");
-          const flags = patternStrings.pop();
-          const parsedPatternString = REWRITE_MATCH_PATTERN.slice(1, REWRITE_MATCH_PATTERN.length - 1 - flags.length);
-          const regExp = new RegExp(parsedPatternString, flags);
-
-          path = path.replace(regExp, REWRITE_SUBSTITUTION);
-        } else {
-          path = path.replace(REWRITE_MATCH_PATTERN, REWRITE_SUBSTITUTION);
+        const REWRITE_MATCH_PATTERNS = parseJson(REWRITE_MATCH_PATTERN);
+        const REWRITE_SUBSTITUTIONS = parseJson(REWRITE_SUBSTITUTION);
+
+        for (let k = 0; k < REWRITE_MATCH_PATTERNS.length; k++) {
+          const matchPattern = REWRITE_MATCH_PATTERNS[k];
+          if (typeof matchPattern === "string") {
+            const regExp = generateRegExp(matchPattern);
+            path = path.replace(regExp, REWRITE_SUBSTITUTIONS[k]);
+            if (generateRegExp(matchPattern).test(path)) break;
+          } else {
+            path = path.replace(matchPattern, REWRITE_SUBSTITUTIONS[k]);
+          }
         }
       }
 
diff --git a/source/image-handler/test/image-request/parse-image-edits.spec.ts b/source/image-handler/test/image-request/parse-image-edits.spec.ts
index c8d4380c5..3fc837818 100644
--- a/source/image-handler/test/image-request/parse-image-edits.spec.ts
+++ b/source/image-handler/test/image-request/parse-image-edits.spec.ts
@@ -72,6 +72,54 @@ describe("parseImageEdits", () => {
     expect(result).toEqual(expectedResult);
   });
 
+  it("Should pass if the proper result is returned for a sample custom-type image request - multipe image rewrite - confirm correct replacement - 1", () => {
+    // Arrange
+    const event = {
+      path: "/thumb/beach-100x100.jpg",
+    };
+
+    /**
+     * a custom request soecifying thumb should return a replacement using the first substitution entry
+     */
+    process.env = {
+      REWRITE_MATCH_PATTERN: '["//thumb/g","//small/g","//large/g"]',
+      REWRITE_SUBSTITUTION:
+        '["/300x300/filters:quality(80)","/fit-in/600x600/filters:quality(80)","/fit-in/1200x1200/filters:quality(80)"]',
+    };
+
+    // Act
+    const imageRequest = new ImageRequest(s3Client, secretProvider);
+    const result = imageRequest.parseImageEdits(event, RequestTypes.CUSTOM);
+
+    // Assert
+    const expectedResult = { jpeg: { quality: 80 }, resize: { height: 300, width: 300 } };
+    expect(result).toEqual(expectedResult);
+  });
+
+  it("Should pass if the proper result is returned for a sample custom-type image request - multipe image rewrite - confirm correct replacement - 2", () => {
+    // Arrange
+    const event = {
+      path: "/large/test.jpg",
+    };
+
+    /**
+     * a custom request specifying large should return a replacement using the third substitution entry which includes a resize
+     */
+    process.env = {
+      REWRITE_MATCH_PATTERN: '["//thumb/g","//small/g","//large/g"]',
+      REWRITE_SUBSTITUTION:
+        '["/300x300/filters:quality(80)","/fit-in/600x600/filters:quality(80)","/fit-in/1200x1200/filters:quality(100)"]',
+    };
+
+    // Act
+    const imageRequest = new ImageRequest(s3Client, secretProvider);
+    const result = imageRequest.parseImageEdits(event, RequestTypes.CUSTOM);
+
+    // Assert
+    const expectedResult = { jpeg: { quality: 100 }, resize: { height: 1200, width: 1200, fit: "inside" } };
+    expect(result).toEqual(expectedResult);
+  });
+
   it("Should throw an error if a requestType is not specified and/or the image edits cannot be parsed", () => {
     // Arrange
     const event = {
diff --git a/source/image-handler/test/image-request/parse-image-key.spec.ts b/source/image-handler/test/image-request/parse-image-key.spec.ts
index 67914dba2..949101646 100644
--- a/source/image-handler/test/image-request/parse-image-key.spec.ts
+++ b/source/image-handler/test/image-request/parse-image-key.spec.ts
@@ -240,6 +240,27 @@ describe("parseImageKey", () => {
     expect(result).toEqual(expectedResult);
   });
 
+  it("Should pass if an image key value is provided in the custom request format - confirm key retrieval when multiple image rewrite specified", () => {
+    // Arrange
+    const event = {
+      path: "/thumb/test.jpg",
+    };
+
+    process.env = {
+      REWRITE_MATCH_PATTERN: '["//thumb/g","//small/g","//large/g"]',
+      REWRITE_SUBSTITUTION:
+        '["/300x300/filters:quality(80)","/fit-in/600x600/filters:quality(80)","/fit-in/1200x1200/filters:quality(80)"]',
+    };
+
+    // Act
+    const imageRequest = new ImageRequest(s3Client, secretProvider);
+    const result = imageRequest.parseImageKey(event, RequestTypes.CUSTOM);
+
+    // Assert
+    const expectedResult = "test.jpg";
+    expect(result).toEqual(expectedResult);
+  });
+
   it("Should throw an error if an unrecognized requestType is passed into the function as a parameter", () => {
     // Arrange
     const event = {
diff --git a/source/image-handler/test/image-request/parse-request-type.spec.ts b/source/image-handler/test/image-request/parse-request-type.spec.ts
index 0759bd8f7..c4dd604da 100644
--- a/source/image-handler/test/image-request/parse-request-type.spec.ts
+++ b/source/image-handler/test/image-request/parse-request-type.spec.ts
@@ -88,6 +88,24 @@ describe("parseRequestType", () => {
     expect(result).toEqual(expectedResult);
   });
 
+  it("Should pass if the method detects a custom request with multiple rewrite patterns", () => {
+    // Arrange
+    const event = { path: "/additionalImageRequestParameters/image.jpg" };
+    process.env = {
+      REWRITE_MATCH_PATTERN: '["//thumb/g","//small/g","//large/g"]',
+      REWRITE_SUBSTITUTION:
+        '["/300x300/filters:quality(80)","/fit-in/600x600/filters:quality(80)","/fit-in/1200x1200/filters:quality(80)"]',
+    };
+
+    // Act
+    const imageRequest = new ImageRequest(s3Client, secretProvider);
+    const result = imageRequest.parseRequestType(event);
+
+    // Assert
+    const expectedResult = RequestTypes.CUSTOM;
+    expect(result).toEqual(expectedResult);
+  });
+
   it("Should throw an error if the method cannot determine the request type based on the three groups given", () => {
     // Arrange
     const event = { path: "12x12e24d234r2ewxsad123d34r.bmp" };
diff --git a/source/image-handler/thumbor-mapper.ts b/source/image-handler/thumbor-mapper.ts
index 5cc7b4c6a..6fc305632 100644
--- a/source/image-handler/thumbor-mapper.ts
+++ b/source/image-handler/thumbor-mapper.ts
@@ -5,6 +5,7 @@ import Color from "color";
 import ColorName from "color-name";
 
 import { ImageEdits, ImageFitTypes, ImageFormatTypes } from "./lib";
+import { parseJson, generateRegExp } from "../solution-utils/helpers";
 
 export class ThumborMapper {
   private static readonly EMPTY_IMAGE_EDITS: ImageEdits = {};
@@ -54,14 +55,18 @@ export class ThumborMapper {
     } else {
       let parsedPath = "";
 
-      if (typeof REWRITE_MATCH_PATTERN === "string") {
-        const patternStrings = REWRITE_MATCH_PATTERN.split("/");
-        const flags = patternStrings.pop();
-        const parsedPatternString = REWRITE_MATCH_PATTERN.slice(1, REWRITE_MATCH_PATTERN.length - 1 - flags.length);
-        const regExp = new RegExp(parsedPatternString, flags);
-        parsedPath = path.replace(regExp, REWRITE_SUBSTITUTION);
-      } else {
-        parsedPath = path.replace(REWRITE_MATCH_PATTERN, REWRITE_SUBSTITUTION);
+      const REWRITE_MATCH_PATTERNS = parseJson(REWRITE_MATCH_PATTERN);
+      const REWRITE_SUBSTITUTIONS = parseJson(REWRITE_SUBSTITUTION);
+
+      for (let k = 0; k < REWRITE_MATCH_PATTERNS.length; k++) {
+        const matchPattern = REWRITE_MATCH_PATTERNS[k];
+        if (typeof matchPattern === "string") {
+          const regExp = generateRegExp(matchPattern);
+          parsedPath = path.replace(regExp, REWRITE_SUBSTITUTIONS[k]);
+          if (generateRegExp(matchPattern).test(path)) break;
+        } else {
+          parsedPath = path.replace(matchPattern, REWRITE_SUBSTITUTIONS[k]);
+        }
       }
 
       return parsedPath;
diff --git a/source/image-handler/tsconfig.json b/source/image-handler/tsconfig.json
index 56ebe595b..95ab2c31d 100644
--- a/source/image-handler/tsconfig.json
+++ b/source/image-handler/tsconfig.json
@@ -10,6 +10,6 @@
     "sourceMap": true,
     "types": ["node", "@types/jest"]
   },
-  "include": ["**/*.ts"],
+  "include": ["**/*.ts", "../solution-utils/test/helpers.spec.ts"],
   "exclude": ["package", "dist", "**/*.map"]
 }
diff --git a/source/solution-utils/helpers.ts b/source/solution-utils/helpers.ts
index 767f3472b..98c111071 100644
--- a/source/solution-utils/helpers.ts
+++ b/source/solution-utils/helpers.ts
@@ -9,3 +9,28 @@
 export function isNullOrWhiteSpace(str: string): boolean {
   return !str || str.replace(/\s/g, "") === "";
 }
+
+/**
+ * Determine if this appears to be json or a plain string
+ * @param str Input string to evaluate
+ * @returns Either a json object or a plain string
+ */
+export function parseJson(str) {
+  try {
+    return JSON.parse(str);
+  } catch (e) {
+    return [str];
+  }
+}
+
+/**
+ * Given a string that may describe actions in an image request, create a regex from the string
+ * @param matchPattern string to operate on
+ * @returns regex
+ */
+export function generateRegExp(matchPattern) {
+  const patternStrings = matchPattern.split("/");
+  const flags = patternStrings.pop();
+  const parsedPatternString = matchPattern.slice(1, matchPattern.length - 1 - flags.length);
+  return new RegExp(parsedPatternString, flags);
+}
diff --git a/source/solution-utils/test/get-options.test.ts b/source/solution-utils/test/get-options.test.ts
index b8da776f6..8ea83e17e 100644
--- a/source/solution-utils/test/get-options.test.ts
+++ b/source/solution-utils/test/get-options.test.ts
@@ -24,6 +24,7 @@ describe("getOptions", () => {
   });
 
   it("will return an empty object when environment variables are missing", () => {
+    // eslint-disable-next-line @typescript-eslint/no-var-requires
     const { getOptions } = require("../get-options");
     expect.assertions(4);
 
@@ -42,6 +43,7 @@ describe("getOptions", () => {
   });
 
   it("will return an object with the custom user agent string", () => {
+    // eslint-disable-next-line @typescript-eslint/no-var-requires
     const { getOptions } = require("../get-options");
     expect.assertions(1);
     expect(getOptions()).toEqual({
diff --git a/source/solution-utils/test/helpers.spec.ts b/source/solution-utils/test/helpers.spec.ts
new file mode 100644
index 000000000..254461662
--- /dev/null
+++ b/source/solution-utils/test/helpers.spec.ts
@@ -0,0 +1,62 @@
+// Copyright Amazon.com, Inc. or its affiliates. All Rights Reserved.
+// SPDX-License-Identifier: Apache-2.0
+
+import { isNullOrWhiteSpace, parseJson, generateRegExp } from "../helpers";
+
+describe("helpers", () => {
+  it("Should pass if the proper result is returned for a whitespace only string", () => {
+    const result = isNullOrWhiteSpace(" ");
+
+    const expectedResult = true;
+    expect(result).toEqual(expectedResult);
+  });
+
+  it("Should pass if the proper result is returned for a null string", () => {
+    const result = isNullOrWhiteSpace("");
+
+    const expectedResult = true;
+    expect(result).toEqual(expectedResult);
+  });
+
+  it("Should pass if the proper result is returned for non-whitespace containing string", () => {
+    const result = isNullOrWhiteSpace("abc");
+
+    const expectedResult = false;
+    expect(result).toEqual(expectedResult);
+  });
+
+  it("Should pass if the proper result is returned for a singe entry", () => {
+    const result = parseJson("filter:");
+
+    const expectedResult = ["filter:"];
+    expect(result).toEqual(expectedResult);
+  });
+
+  it("Should pass if the proper result is returned for a null string", () => {
+    const result = parseJson("");
+
+    const expectedResult = [""];
+    expect(result).toEqual(expectedResult);
+  });
+
+  it("Should pass if the proper result is returned for json with multiple objects", () => {
+    const result = parseJson('["//thumb/g","//small/g","//large/g"]');
+
+    const expectedResult = ["//thumb/g", "//small/g", "//large/g"];
+    expect(result).toEqual(expectedResult);
+  });
+
+  it("Should pass if the proper result is returned for a simple regex", () => {
+    const result = generateRegExp("/thumb/g");
+
+    const expectedResult1 = /thumb/g;
+    expect(result).toEqual(expectedResult1);
+  });
+
+  it("Should pass if the proper result is returned for a simple rege with embedded slash that must be escaped", () => {
+    const result = generateRegExp("//thumb/g");
+
+    const expectedResult1 = /\/thumb/g;
+    expect(result).toEqual(expectedResult1);
+  });
+});
diff --git a/source/solution-utils/tsconfig.json b/source/solution-utils/tsconfig.json
index 56ebe595b..f5ec83c87 100644
--- a/source/solution-utils/tsconfig.json
+++ b/source/solution-utils/tsconfig.json
@@ -10,6 +10,6 @@
     "sourceMap": true,
     "types": ["node", "@types/jest"]
   },
-  "include": ["**/*.ts"],
+  "include": ["**/*.ts", "test/helpers.spec.ts"],
   "exclude": ["package", "dist", "**/*.map"]
 }