diff --git a/src/services/uploads/package.json b/src/services/uploads/package.json
index c23c02631..741c8ee54 100644
--- a/src/services/uploads/package.json
+++ b/src/services/uploads/package.json
@@ -7,5 +7,8 @@
   "scripts": {},
   "author": "",
   "license": "CC0-1.0",
-  "devDependencies": {}
+  "devDependencies": {},
+  "dependencies": {
+    "file-type": "^19.0.0"
+  }
 }
diff --git a/src/services/uploads/serverless.yml b/src/services/uploads/serverless.yml
index a572c3f0d..0588fdb07 100644
--- a/src/services/uploads/serverless.yml
+++ b/src/services/uploads/serverless.yml
@@ -29,6 +29,7 @@ provider:
             - s3:PutObjectVersionTagging
             - s3:DeleteObject
             - s3:ListBucket
+            - s3:HeadObject
           Resource:
             - !Sub arn:aws:s3:::${self:service}-${sls:stage}-attachments-${AWS::AccountId}/*
             - !Sub arn:aws:s3:::${self:service}-${sls:stage}-avscan-${AWS::AccountId}/*
diff --git a/src/services/uploads/src/antivirus.ts b/src/services/uploads/src/antivirus.ts
index 2e0a2d811..cacf95873 100644
--- a/src/services/uploads/src/antivirus.ts
+++ b/src/services/uploads/src/antivirus.ts
@@ -88,7 +88,11 @@ const scanAndTagS3Object = async (
       s3ObjectBucket
     );
     utils.generateSystemMessage("Set virusScanStatus");
-    virusScanStatus = scanLocalFile(fileLoc);
+    const metadata = await s3Client.send(new HeadObjectCommand({
+      Bucket: s3ObjectBucket,
+      Key: s3ObjectKey,
+    }));
+    virusScanStatus = await scanLocalFile(fileLoc, metadata.ContentType);
     utils.generateSystemMessage(`virusScanStatus=${virusScanStatus}`);
   }
 
diff --git a/src/services/uploads/src/clamav.ts b/src/services/uploads/src/clamav.ts
index 19c6d5d05..4a9476582 100644
--- a/src/services/uploads/src/clamav.ts
+++ b/src/services/uploads/src/clamav.ts
@@ -11,6 +11,7 @@ import fs from "fs";
 import asyncfs from "fs/promises";
 import * as constants from "./constants";
 import * as utils from "./utils";
+import {FileExtension, MimeType, fileTypeFromFile} from 'file-type';
 
 const s3Client: S3Client = new S3Client();
 
@@ -206,8 +207,23 @@ export const uploadAVDefinitions = async (): Promise<void[]> => {
  *
  * @param pathToFile Path in the filesystem where the file is stored.
  */
-export const scanLocalFile = (pathToFile: string): string | null => {
+export const scanLocalFile = async (pathToFile: string, contentType: string | undefined): Promise<string | null> => {
   try {
+    if(!contentType){
+      utils.generateSystemMessage("FAILURE - EXTENSION UNKNOWN");
+      return constants.STATUS_UNKNOWN_EXTENSION;
+    }
+    let detectedContentType = await getFileTypeFromContents(pathToFile);
+    if(detectedContentType){
+      console.log(`File declared extension:  ${contentType}`); 
+      console.log(`File detected extension:  ${detectedContentType}`)
+      let same = areMimeTypesEquivalent(contentType, detectedContentType)
+      if(!same){
+        utils.generateSystemMessage(`FAILURE - FILE EXTENSION DOES NOT MATCH FILE CONTENTS`);
+        return constants.STATUS_EXTENSION_MISMATCH_FILE
+      }
+    }
+
     const avResult: SpawnSyncReturns<Buffer> = spawnSync(
       constants.PATH_TO_CLAMAV,
       [
@@ -241,4 +257,44 @@ export const scanLocalFile = (pathToFile: string): string | null => {
     console.log(err);
     return constants.STATUS_ERROR_PROCESSING_FILE;
   }
-};
\ No newline at end of file
+};
+
+async function getFileTypeFromContents(filePath: string): Promise<MimeType | null> {
+  try {
+      const fileBuffer = await fs.promises.readFile(filePath);
+
+      // Get the file type from its contents
+      const type = await fileTypeFromFile(filePath);
+
+      if (!type) {
+        console.log('Could not determine file type.');
+        return null;
+      }
+      console.log(`File type is ${type.mime} with extension ${type.ext}`);
+      return type.mime
+  } catch (error) {
+      console.error('Error reading file:', error);
+      return null
+  }
+}
+
+function areMimeTypesEquivalent(mime1: string, mime2: string): boolean {
+  const equivalentTypes: { [key: string]: Set<string> } = {
+      'application/rtf': new Set(['text/rtf']),
+      'application/vnd.ms-excel': new Set(['application/x-cfb']),
+      'application/vnd.ms-powerpoint': new Set(['application/x-cfb']),
+      'application/msword': new Set(['application/x-cfb'])
+  };
+  mime1 = mime1.toLowerCase();
+  mime2 = mime2.toLowerCase();
+  if (mime1 === mime2) {
+      return true;
+  }
+  for (const baseType in equivalentTypes) {
+      const equivalents = equivalentTypes[baseType];
+      if ((mime1 === baseType && equivalents.has(mime2)) || (mime2 === baseType && equivalents.has(mime1))) {
+          return true;
+      }
+  }
+  return false;
+}
\ No newline at end of file
diff --git a/src/services/uploads/src/constants.ts b/src/services/uploads/src/constants.ts
index 61325d3bc..9d1dc060d 100644
--- a/src/services/uploads/src/constants.ts
+++ b/src/services/uploads/src/constants.ts
@@ -39,6 +39,10 @@ export const STATUS_ERROR_PROCESSING_FILE: string =
   process.env.STATUS_ERROR_PROCESSING_FILE || "ERROR";
 export const STATUS_SKIPPED_FILE: string =
   process.env.STATUS_SKIPPED_FILE || "SKIPPED";
+export const STATUS_EXTENSION_MISMATCH_FILE: string = 
+  process.env.STATUS_EXTENSION_MISMATCH_FILE || "EXTMISMATCH"
+export const STATUS_UNKNOWN_EXTENSION: string = 
+  process.env.STATUS_UNKNOWN_EXTENSION || "UKNOWNEXT"
 export const VIRUS_SCAN_STATUS_KEY: string =
   process.env.VIRUS_SCAN_STATUS_KEY || "virusScanStatus";
 export const VIRUS_SCAN_TIMESTAMP_KEY: string =
diff --git a/yarn.lock b/yarn.lock
index eef264b51..938c3a4a5 100644
--- a/yarn.lock
+++ b/yarn.lock
@@ -10183,6 +10183,15 @@ file-type@^16.5.4:
     strtok3 "^6.2.4"
     token-types "^4.1.1"
 
+file-type@^19.0.0:
+  version "19.0.0"
+  resolved "https://registry.yarnpkg.com/file-type/-/file-type-19.0.0.tgz#62a6cadc43f73ba38c53e1a174943a75fdafafa9"
+  integrity sha512-s7cxa7/leUWLiXO78DVVfBVse+milos9FitauDLG1pI7lNaJ2+5lzPnr2N24ym+84HVwJL6hVuGfgVE+ALvU8Q==
+  dependencies:
+    readable-web-to-node-stream "^3.0.2"
+    strtok3 "^7.0.0"
+    token-types "^5.0.1"
+
 file-type@^3.8.0:
   version "3.9.0"
   resolved "https://registry.yarnpkg.com/file-type/-/file-type-3.9.0.tgz#257a078384d1db8087bc449d107d52a52672b9e9"
@@ -13784,6 +13793,11 @@ peek-readable@^4.1.0:
   resolved "https://registry.yarnpkg.com/peek-readable/-/peek-readable-4.1.0.tgz#4ece1111bf5c2ad8867c314c81356847e8a62e72"
   integrity sha512-ZI3LnwUv5nOGbQzD9c2iDG6toheuXSZP5esSHBjopsXH4dg19soufvpUGA3uohi5anFtGb2lhAVdHzH6R/Evvg==
 
+peek-readable@^5.0.0:
+  version "5.0.0"
+  resolved "https://registry.yarnpkg.com/peek-readable/-/peek-readable-5.0.0.tgz#7ead2aff25dc40458c60347ea76cfdfd63efdfec"
+  integrity sha512-YtCKvLUOvwtMGmrniQPdO7MwPjgkFBtFIrmfSbYmYuq3tKDV/mcfAhBth1+C3ru7uXIZasc/pHnb+YDYNkkj4A==
+
 pend@~1.2.0:
   version "1.2.0"
   resolved "https://registry.yarnpkg.com/pend/-/pend-1.2.0.tgz#7a57eb550a6783f9115331fcf4663d5c8e007a50"
@@ -14420,7 +14434,7 @@ readable-stream@^4.2.0:
     process "^0.11.10"
     string_decoder "^1.3.0"
 
-readable-web-to-node-stream@^3.0.0:
+readable-web-to-node-stream@^3.0.0, readable-web-to-node-stream@^3.0.2:
   version "3.0.2"
   resolved "https://registry.yarnpkg.com/readable-web-to-node-stream/-/readable-web-to-node-stream-3.0.2.tgz#5d52bb5df7b54861fd48d015e93a2cb87b3ee0bb"
   integrity sha512-ePeK6cc1EcKLEhJFt/AebMCLL+GgSKhuygrZ/GLaKZYEecIgIECf4UaUuaByiGtzckwR4ain9VzUh95T1exYGw==
@@ -15425,6 +15439,14 @@ strtok3@^6.2.4:
     "@tokenizer/token" "^0.3.0"
     peek-readable "^4.1.0"
 
+strtok3@^7.0.0:
+  version "7.0.0"
+  resolved "https://registry.yarnpkg.com/strtok3/-/strtok3-7.0.0.tgz#868c428b4ade64a8fd8fee7364256001c1a4cbe5"
+  integrity sha512-pQ+V+nYQdC5H3Q7qBZAz/MO6lwGhoC2gOAjuouGf/VO0m7vQRh8QNMl2Uf6SwAtzZ9bOw3UIeBukEGNJl5dtXQ==
+  dependencies:
+    "@tokenizer/token" "^0.3.0"
+    peek-readable "^5.0.0"
+
 styled-components@^5.3.5:
   version "5.3.11"
   resolved "https://registry.yarnpkg.com/styled-components/-/styled-components-5.3.11.tgz#9fda7bf1108e39bf3f3e612fcc18170dedcd57a8"
@@ -15782,6 +15804,14 @@ token-types@^4.1.1:
     "@tokenizer/token" "^0.3.0"
     ieee754 "^1.2.1"
 
+token-types@^5.0.1:
+  version "5.0.1"
+  resolved "https://registry.yarnpkg.com/token-types/-/token-types-5.0.1.tgz#aa9d9e6b23c420a675e55413b180635b86a093b4"
+  integrity sha512-Y2fmSnZjQdDb9W4w4r1tswlMHylzWIeOKpx0aZH9BgGtACHhrk3OkT52AzwcuqTRBZtvvnTjDBh8eynMulu8Vg==
+  dependencies:
+    "@tokenizer/token" "^0.3.0"
+    ieee754 "^1.2.1"
+
 totalist@^3.0.0:
   version "3.0.1"
   resolved "https://registry.yarnpkg.com/totalist/-/totalist-3.0.1.tgz#ba3a3d600c915b1a97872348f79c127475f6acf8"