diff --git a/package.json b/package.json
index 5a399cc0..f1ae2db5 100644
--- a/package.json
+++ b/package.json
@@ -13,20 +13,27 @@
   },
   "dependencies": {
     "@octokit/rest": "^16.28.7",
-    "@types/express": "^4.17.0",
-    "@types/ioredis": "^4.0.13",
-    "@types/markdown-it": "^0.0.8",
     "express": "^4.17.1",
     "ioredis": "^4.14.0",
     "markdown-it": "^9.0.1",
     "matrix-bot-sdk": "^0.3.9",
     "micromatch": "^4.0.2",
+    "mime": "^2.4.4",
+    "mocha": "^6.2.0",
+    "node-emoji": "^1.10.0",
+    "request-promise-native": "^1.0.7",
     "winston": "^3.2.1",
     "yaml": "^1.6.0"
   },
   "devDependencies": {
+    "@types/express": "^4.17.0",
+    "@types/ioredis": "^4.0.13",
+    "@types/markdown-it": "^0.0.8",
     "@types/micromatch": "^3.1.0",
+    "@types/mime": "^2.0.1",
     "@types/node": "^12.6.9",
+    "@types/node-emoji": "^1.8.1",
+    "@types/request-promise-native": "^1.0.16",
     "@types/yaml": "^1.0.2",
     "typescript": "^3.5.3"
   }
diff --git a/src/CommentProcessor.ts b/src/CommentProcessor.ts
index c78d5027..990150f7 100644
--- a/src/CommentProcessor.ts
+++ b/src/CommentProcessor.ts
@@ -1,9 +1,13 @@
 import { IssuesGetCommentResponse } from "@octokit/rest";
 import { Appservice } from "matrix-bot-sdk";
+import request from "request-promise-native";
 import markdown from "markdown-it";
+import mime from "mime";
+import emoji from "node-emoji";
 
 const md = new markdown();
 const REGEX_MENTION = /(^|\s)(@[a-z\d](?:[a-z\d]|-(?=[a-z\d])){0,38})(\s|$)/ig;
+const REGEX_IMAGES = /!\[.*]\((.*\.(\w+))\)/gm;
 
 interface IMatrixCommentEvent {
     msgtype: string;
@@ -19,15 +23,16 @@ interface IMatrixCommentEvent {
 export class CommentProcessor {
     constructor (private as: Appservice) {}
 
-    public getEventBodyForComment(comment: IssuesGetCommentResponse): IMatrixCommentEvent {
+    public async getEventBodyForComment(comment: IssuesGetCommentResponse): Promise<IMatrixCommentEvent> {
         let body = comment.body;
-        body = body.replace(REGEX_MENTION, (_match: string, _part1: string, githubId: string) => {
-            const userId = this.as.getUserIdForSuffix(githubId.substr(1));
-            return `[$2](https://matrix.to/#/${userId})`;
-        });
+        body = this.replaceMentions(body);
+        body = await this.replaceImages(body);
+        body = emoji.emojify(body);
+        let htmlBody = md.render(body);
+        console.log(body, htmlBody);
         return {
             body,
-            formatted_body: md.render(body),
+            formatted_body: htmlBody,
             msgtype: "m.text",
             format: "org.matrix.custom.html",
             external_url: comment.html_url,
@@ -36,4 +41,37 @@ export class CommentProcessor {
             },
         }
     }
+
+    private replaceMentions(body: string): string {
+        return body.replace(REGEX_MENTION, (_match: string, _part1: string, githubId: string) => {
+            const userId = this.as.getUserIdForSuffix(githubId.substr(1));
+            return `[$2](https://matrix.to/#/${userId})`;
+        });
+    }
+
+    private async replaceImages(body: string): Promise<string> {
+        let match;
+        let bodyCopy = body;
+        let urlMatches: string[] = [];
+        while(match = REGEX_IMAGES.exec(bodyCopy)) {
+            bodyCopy = bodyCopy.replace(match[1], "");
+            const contentType = mime.getType(match[1]) || "none";
+            if (!contentType.startsWith("image") && !contentType.startsWith("video") && !contentType.startsWith("audio")) {
+                // Not handling media.
+                continue;
+            }
+            urlMatches.push(match[1]);
+        }
+        for (const rawUrl of urlMatches) {
+            try {
+                const imageData = await request.get(rawUrl, { encoding: null});
+                const contentType = mime.getType(rawUrl) || "application/octet-stream";
+                const url = await this.as.botIntent.underlyingClient.uploadContent(imageData, contentType);
+                body = body.replace(rawUrl, url);
+            } catch (ex) {
+                console.warn("Failed to upload file");
+            }
+        }
+        return body;
+    }
 }
\ No newline at end of file