diff --git a/src/s3/correctContentType.ts b/src/s3/correctContentType.ts
index 58ef9d3..e4235b1 100644
--- a/src/s3/correctContentType.ts
+++ b/src/s3/correctContentType.ts
@@ -249,6 +249,8 @@ for (const objectKey of allObjects) {
       console.log(`✗ Skipped ${objectKey}`);
       skippedCount = skippedCount + 1;
     }
+  } else {
+    console.log(`✓ ${objectKey} is already correct: ${currentContentType ?? "undefined"}`);
   }
 }
 
diff --git a/src/s3/upload.ts b/src/s3/upload.ts
index d5f9cd1..f657f1d 100644
--- a/src/s3/upload.ts
+++ b/src/s3/upload.ts
@@ -4,7 +4,7 @@
  * @author Naomi Carrigan
  */
 import { readFile } from "node:fs/promises";
-import { join } from "node:path";
+import { extname, join } from "node:path";
 import { S3Client, PutObjectCommand } from "@aws-sdk/client-s3";
 import { input } from "@inquirer/prompts";
 
@@ -43,13 +43,92 @@ const s3 = new S3Client({
   region:      "hel1",
 });
 
+/**
+ * MIME type mapping for file extensions.
+ */
+/* eslint-disable @typescript-eslint/naming-convention -- File extensions */
+/* eslint-disable stylistic/key-spacing -- Alignment for readability */
+const mimeTypes: Record<string, string> = {
+  ".7z": "application/x-7z-compressed",
+  ".aac": "audio/aac",
+  ".avi": "video/x-msvideo",
+  ".bmp": "image/bmp",
+  ".css": "text/css",
+  ".csv": "text/csv",
+  ".doc": "application/msword",
+  ".docx":
+    "application/vnd.openxmlformats-officedocument.wordprocessingml.document",
+  ".eot": "application/vnd.ms-fontobject",
+  ".flac": "audio/flac",
+  ".gif": "image/gif",
+  ".gz": "application/gzip",
+  ".htm": "text/html",
+  ".html": "text/html",
+  ".ico": "image/x-icon",
+  ".jpeg": "image/jpeg",
+  ".jpg": "image/jpeg",
+  ".js": "text/javascript",
+  ".json": "application/json",
+  ".md": "text/markdown",
+  ".mkv": "video/x-matroska",
+  ".mov": "video/quicktime",
+  ".mp3": "audio/mpeg",
+  ".mp4": "video/mp4",
+  ".ogg": "audio/ogg",
+  ".otf": "font/otf",
+  ".pdf": "application/pdf",
+  ".png": "image/png",
+  ".ppt": "application/vnd.ms-powerpoint",
+  ".pptx":
+    "application/vnd.openxmlformats-officedocument.presentationml.presentation",
+  ".rar": "application/x-rar-compressed",
+  ".svg": "image/svg+xml",
+  ".tar": "application/x-tar",
+  ".tif": "image/tiff",
+  ".tiff": "image/tiff",
+  ".ttf": "font/ttf",
+  ".txt": "text/plain",
+  ".wav": "audio/wav",
+  ".webm": "video/webm",
+  ".webp": "image/webp",
+  ".woff": "font/woff",
+  ".woff2": "font/woff2",
+  ".xls": "application/vnd.ms-excel",
+  ".xlsx":
+    "application/vnd.openxmlformats-officedocument.spreadsheetml.sheet",
+  ".xml": "application/xml",
+  ".zip": "application/zip",
+};
+/* eslint-enable @typescript-eslint/naming-convention -- File extensions */
+/* eslint-enable stylistic/key-spacing -- Alignment for readability */
+
+/**
+ * Gets the MIME type for a file based on its extension.
+ * @param filePath - The file name or path.
+ * @returns The MIME type, or undefined if unknown.
+ */
+const getMimeType = (filePath: string): string | undefined => {
+  const extension = extname(filePath).toLowerCase();
+  return mimeTypes[extension];
+};
+
+const contentType = getMimeType(uploadPath);
+
+if (contentType === undefined) {
+  console.warn(
+    `Warning: Unknown file type for ${uploadPath}. Content type will not be set.`,
+  );
+}
+
 const command = new PutObjectCommand({
   // eslint-disable-next-line @typescript-eslint/naming-convention -- AWS SDK
-  Body:   file,
+  Body:        file,
   // eslint-disable-next-line @typescript-eslint/naming-convention -- AWS SDK
-  Bucket: "nhcarrigan",
+  Bucket:      "nhcarrigan",
   // eslint-disable-next-line @typescript-eslint/naming-convention -- AWS SDK
-  Key:    uploadPath,
+  ContentType: contentType,
+  // eslint-disable-next-line @typescript-eslint/naming-convention -- AWS SDK
+  Key:         uploadPath,
 });
 
 await s3.send(command);