diff --git a/jobs/jobsDeleteMedia.ts b/jobs/jobsDeleteMedia.ts
index 6d79969..96423d9 100644
--- a/jobs/jobsDeleteMedia.ts
+++ b/jobs/jobsDeleteMedia.ts
@@ -1,15 +1,9 @@
 import { Request, Response } from "express";
 import fs from "fs-extra";
-import path from "path";
 import { logger } from "../server";
-import GenerateThumbnail from "../util/generateThumbnail";
 import MediaFile from "../util/interfaces/MediaFile";
-import ListableChecker from "../util/listableChecker";
-import GenerateUrl from "../util/MediaUrlGen";
 import { PathToRoFolder } from "../util/pathGenerators";
-import { FolderPaths, JobRelativeFilePath } from "../util/serverInit";
-import ft from "file-type";
-import core from "file-type/core";
+import { JobRelativeFilePath } from "../util/serverInit";
 
 export async function JobsDeleteMedia(req: Request, res: Response) {
   const jobid: string = (req.body.jobid || "").trim();
diff --git a/jobs/jobsDownloadMedia.ts b/jobs/jobsDownloadMedia.ts
index 42973ad..0fc39a2 100644
--- a/jobs/jobsDownloadMedia.ts
+++ b/jobs/jobsDownloadMedia.ts
@@ -1,15 +1,10 @@
 import { Request, Response } from "express";
 import fs from "fs-extra";
-import multer from "multer";
+import JSZip from "jszip";
 import path from "path";
 import { logger } from "../server";
-import GenerateThumbnail from "../util/generateThumbnail";
-import generateUniqueFilename from "../util/generateUniqueFilename";
-import { ConvertHeicFiles } from "../util/heicConverter";
-import { PathToRoFolder } from "../util/pathGenerators";
-import { JobsListMedia } from "./jobsListMedia";
-import JSZip from "jszip";
 import ListableChecker from "../util/listableChecker";
+import { PathToRoFolder } from "../util/pathGenerators";
 import { JobRelativeFilePath } from "../util/serverInit";
 
 //param: files: string[] | array of filenames.
diff --git a/jobs/jobsListMedia.ts b/jobs/jobsListMedia.ts
index 8240c20..ce8cae2 100644
--- a/jobs/jobsListMedia.ts
+++ b/jobs/jobsListMedia.ts
@@ -2,7 +2,9 @@ import { Request, Response } from "express";
 import fs from "fs-extra";
 import path from "path";
 import { logger } from "../server";
-import GenerateThumbnail from "../util/generateThumbnail";
+import GenerateThumbnail, {
+  GenerateOptimized,
+} from "../util/generateThumbnail";
 import MediaFile from "../util/interfaces/MediaFile";
 import ListableChecker from "../util/listableChecker";
 import GenerateUrl from "../util/MediaUrlGen";
@@ -29,6 +31,9 @@ export async function JobsListMedia(req: Request, res: Response) {
           const relativeThumbPath: string = await GenerateThumbnail(
             relativeFilePath
           );
+          const relativeOptimizedPath: string = await GenerateOptimized(
+            relativeFilePath
+          );
 
           const type: core.FileTypeResult | undefined = await ft.fromFile(
             relativeFilePath
@@ -49,6 +54,12 @@ export async function JobsListMedia(req: Request, res: Response) {
               jobid,
               relativeThumbPath,
             ]),
+            optimized: GenerateUrl([
+              FolderPaths.StaticPath,
+              FolderPaths.JobsFolder,
+              jobid,
+              relativeOptimizedPath,
+            ]),
             thumbnailHeight: 250,
             thumbnailWidth: 250,
             filename: file.filename,
@@ -73,6 +84,9 @@ export async function JobsListMedia(req: Request, res: Response) {
           const relativeThumbPath: string = await GenerateThumbnail(
             relativeFilePath
           );
+          const relativeOptimizedPath: string = await GenerateOptimized(
+            relativeFilePath
+          );
           const type: core.FileTypeResult | undefined = await ft.fromFile(
             relativeFilePath
           );
@@ -92,6 +106,12 @@ export async function JobsListMedia(req: Request, res: Response) {
               jobid,
               relativeThumbPath,
             ]),
+            optimized: GenerateUrl([
+              FolderPaths.StaticPath,
+              FolderPaths.JobsFolder,
+              jobid,
+              relativeOptimizedPath,
+            ]),
             thumbnailHeight: 250,
             thumbnailWidth: 250,
             filename: file.name,
diff --git a/jobs/jobsMoveMedia.ts b/jobs/jobsMoveMedia.ts
index 6f90851..445e8cc 100644
--- a/jobs/jobsMoveMedia.ts
+++ b/jobs/jobsMoveMedia.ts
@@ -1,13 +1,10 @@
 import { Request, Response } from "express";
 import fs from "fs-extra";
 import path from "path";
-import GenerateThumbnail from "../util/generateThumbnail";
-import GenerateUrl from "../util/MediaUrlGen";
-import { FolderPaths } from "../util/serverInit";
-import multer from "multer";
-import { JobsListMedia } from "./jobsListMedia";
-import { PathToRoFolder } from "../util/pathGenerators";
 import { logger } from "../server";
+import { PathToRoFolder } from "../util/pathGenerators";
+import { FolderPaths } from "../util/serverInit";
+import { JobsListMedia } from "./jobsListMedia";
 
 export async function JobsMoveMedia(req: Request, res: Response) {
   const jobid: string = (req.body.jobid || "").trim();
diff --git a/jobs/jobsUploadMedia.ts b/jobs/jobsUploadMedia.ts
index f196ed7..23ecf7b 100644
--- a/jobs/jobsUploadMedia.ts
+++ b/jobs/jobsUploadMedia.ts
@@ -3,7 +3,9 @@ import fs from "fs-extra";
 import multer from "multer";
 import path from "path";
 import { logger } from "../server";
-import GenerateThumbnail from "../util/generateThumbnail";
+import GenerateThumbnail, {
+  GenerateOptimized,
+} from "../util/generateThumbnail";
 import generateUniqueFilename from "../util/generateUniqueFilename";
 import { ConvertHeicFiles } from "../util/heicConverter";
 import { PathToRoFolder } from "../util/pathGenerators";
@@ -60,6 +62,7 @@ export async function jobsUploadMedia(req: Request, res: Response) {
       //for each file.path, generate the thumbnail.
       (req.files as Express.Multer.File[]).forEach((file) => {
         thumbnailGenerationQueue.push(GenerateThumbnail(file.path));
+        thumbnailGenerationQueue.push(GenerateOptimized(file.path));
       });
 
       await Promise.all(thumbnailGenerationQueue);
diff --git a/util/generateThumbnail.ts b/util/generateThumbnail.ts
index 36529e1..36239ce 100644
--- a/util/generateThumbnail.ts
+++ b/util/generateThumbnail.ts
@@ -1,13 +1,12 @@
-import fs from "fs-extra";
-import { access } from "fs/promises";
-import imageThumbnail from "image-thumbnail";
-import path from "path";
-import gm from "gm";
 import ft from "file-type";
 import core from "file-type/core";
-import GenerateUrl from "./MediaUrlGen";
-import { AssetPaths, FolderPaths } from "./serverInit";
+import fs from "fs-extra";
+import { access } from "fs/promises";
+import gm from "gm";
+import imageThumbnail from "image-thumbnail";
+import path from "path";
 import { logger } from "../server";
+import { AssetPaths, FolderPaths } from "./serverInit";
 const simpleThumb = require("simple-thumbnail");
 const ffmpeg = require("ffmpeg-static");
 
@@ -67,6 +66,67 @@ export default async function GenerateThumbnail(
   }
 }
 
+/** @returns {string} Returns the relative path from the file to the thumbnail on the server. This must be converted to a URL. */
+export async function GenerateOptimized(
+  file: string
+  //thumbPath: string
+) {
+  const type: core.FileTypeResult | undefined = await ft.fromFile(file);
+  let thumbnailExtension: string = GetThumbnailExtension(type, true);
+  let thumbPath: string = path.join(
+    path.dirname(file),
+    FolderPaths.OptimizedSubDir,
+    path.parse(path.basename(file)).name + thumbnailExtension
+  );
+
+  try {
+    //Ensure the thumbs directory exists.
+    await fs.ensureDir(path.dirname(thumbPath));
+
+    try {
+      await access(thumbPath);
+      logger.debug("Optimized image already exists for : " + thumbPath);
+
+      return path.relative(path.dirname(file), thumbPath);
+    } catch {}
+
+    //Check to see if the file is an image, PDF, or video.
+
+    if (type?.mime === "application/pdf") {
+      const fileOnDisk: Buffer = await fs.readFile(file);
+      await GeneratePdfThumbnail(file, thumbPath);
+    } else if (type?.mime.startsWith("video")) {
+      await simpleThumb(file, thumbPath, "250x?", {
+        path: ffmpeg,
+      });
+    } else {
+      logger.debug("Optimized image being created for : " + thumbPath);
+      await OptimizeImage(file, thumbPath);
+    }
+    return path.relative(path.dirname(file), thumbPath);
+  } catch (err) {
+    logger.error("Error when genenerating optimized image:", {
+      thumbPath,
+      err,
+      message: (err as Error).message,
+    });
+    return path.relative(path.dirname(file), AssetPaths.File);
+  }
+}
+
+async function OptimizeImage(file: string, optimizedPath: string) {
+  const fileOnDisk: Buffer = await fs.readFile(file);
+  return new Promise<string>((resolve, reject) => {
+    const result = gm(fileOnDisk)
+      .resize(1500)
+      .quality(75)
+      .write(optimizedPath, (error) => {
+        if (error) reject(error.message);
+        resolve(optimizedPath);
+      });
+  });
+}
+
 async function GeneratePdfThumbnail(file: string, thumbPath: string) {
   const fileOnDisk: Buffer = await fs.readFile(file);
   return new Promise<string>((resolve, reject) => {
@@ -82,7 +142,11 @@ async function GeneratePdfThumbnail(file: string, thumbPath: string) {
   });
 }
 
-function GetThumbnailExtension(file: core.FileTypeResult | undefined) {
+function GetThumbnailExtension(
+  file: core.FileTypeResult | undefined,
+  useJpeg?: boolean
+) {
+  if (useJpeg) return ".jpg";
   if (file === undefined) return ".png";
   return ".png";
 }
diff --git a/util/heicConverter.ts b/util/heicConverter.ts
index e8a6a49..f93727b 100644
--- a/util/heicConverter.ts
+++ b/util/heicConverter.ts
@@ -1,22 +1,13 @@
-import { Request, Response } from "express";
-import multer from "multer";
 
-import GenerateThumbnail from "../util/generateThumbnail";
-import generateUniqueFilename from "../util/generateUniqueFilename";
-import { PathToRoFolder } from "../util/pathGenerators";
 
 import fs from "fs-extra";
 
-import { access } from "fs/promises";
-import imageThumbnail from "image-thumbnail";
-import path, { resolve } from "path";
-import gm from "gm";
+import dotenv from "dotenv";
 import ft from "file-type";
 import core from "file-type/core";
-import GenerateUrl from "./MediaUrlGen";
-import { FolderPaths } from "./serverInit";
+import path, { resolve } from "path";
 import { logger } from "../server";
-import dotenv from "dotenv";
+import { FolderPaths } from "./serverInit";
 
 const heicConverter = require("heic-convert");
 
diff --git a/util/serverInit.ts b/util/serverInit.ts
index 4fc0419..6a9eb2b 100644
--- a/util/serverInit.ts
+++ b/util/serverInit.ts
@@ -17,6 +17,7 @@ export const FolderPaths = {
   Jobs: path.join(RootDirectory, JobsFolder),
   Vendors: path.join(RootDirectory, VendorsFolder),
   ThumbsSubDir: "/thumbs",
+  OptimizedSubDir: "/optimized",
   BillsSubDir: "/bills",
   ConvertedOriginalSubDir: "/ConvertedOriginal",
   StaticPath: "/static",