diff --git a/server/package.json b/server/package.json
index 1f2733109..a1f724c34 100644
--- a/server/package.json
+++ b/server/package.json
@@ -75,7 +75,8 @@
 		"safe-json-stringify": "1.2.0",
 		"tachi-common": "0.2.18",
 		"typescript": "4.3.4",
-		"winston": "3.3.3"
+		"winston": "3.3.3",
+		"winston-transport": "^4.4.0"
 	},
 	"nyc": {
 		"reporter": [
diff --git a/server/pnpm-lock.yaml b/server/pnpm-lock.yaml
index b13177bc4..b5cbd4224 100644
--- a/server/pnpm-lock.yaml
+++ b/server/pnpm-lock.yaml
@@ -61,6 +61,7 @@ specifiers:
   typescript: 4.3.4
   why-is-node-running: 2.2.0
   winston: 3.3.3
+  winston-transport: ^4.4.0
 
 dependencies:
   bcryptjs: 2.4.3
@@ -91,6 +92,7 @@ dependencies:
   tachi-common: 0.2.18
   typescript: 4.3.4
   winston: 3.3.3
+  winston-transport: 4.4.0
 
 devDependencies:
   '@types/bcrypt': 5.0.0
diff --git a/server/src/lib/logger/colours.ts b/server/src/lib/logger/colours.ts
new file mode 100644
index 000000000..ac4c84ef4
--- /dev/null
+++ b/server/src/lib/logger/colours.ts
@@ -0,0 +1,20 @@
+const Colours = {
+	crit: ["bgRed", "black"],
+	severe: ["bgBrightRed", "black"],
+	error: ["red"],
+	warn: ["yellow"],
+	info: ["blue"],
+	verbose: ["cyan"],
+	debug: ["white"],
+};
+
+// Discord ONLY accepts decimal colours, so.
+// lets run with that.
+export const DiscordColours = {
+	crit: 16711680, // #ff0000
+	severe: 16719904, // #ff3333
+	error: 11730944, // #cc0000
+	warn: 16703232, // #ffcc00
+	// other ones dont matter
+};
+export default Colours;
diff --git a/server/src/lib/logger/discord-transport.ts b/server/src/lib/logger/discord-transport.ts
new file mode 100644
index 000000000..e60e146d7
--- /dev/null
+++ b/server/src/lib/logger/discord-transport.ts
@@ -0,0 +1,128 @@
+import { ServerConfig } from "lib/setup/config";
+import SafeJSONStringify from "safe-json-stringify";
+import fetch from "utils/fetch";
+import Transport, { TransportStreamOptions } from "winston-transport";
+import { DiscordColours } from "./colours";
+
+interface DiscordTransportOptions extends TransportStreamOptions {
+	/** Webhook obtained from Discord */
+	webhook: string;
+}
+
+/**
+ * Creates a discord winston transport. This is a slightly adapted version
+ * of sidhantpanda's winston-discord-transport, modified for our use case.
+ *
+ * @param webhookUrl The webhook to connect to.
+ * @returns A winston tranport.
+ */
+export default class DiscordTransport extends Transport {
+	private webhookUrl = "";
+
+	/** Initialization promise resolved after retrieving discord id and token */
+	private initalised: Promise<void>;
+
+	constructor(opts: DiscordTransportOptions) {
+		super(opts);
+
+		this.initalised = fetch(opts.webhook)
+			.then((r) => {
+				if (!r.ok) {
+					throw new Error(`Couldn't connect to discord transport. ${r.status}.`);
+				}
+
+				return r.json();
+			})
+			.then((content) => {
+				this.webhookUrl = `https://discordapp.com/api/v6/webhooks/${content.id}/${content.token}`;
+			});
+	}
+
+	log(info: any, cb: () => void) {
+		if (info.noDiscord !== false) {
+			try {
+				setImmediate(() => {
+					this.initalised.then(() => {
+						this.SendToDiscord(this.webhookUrl, info);
+					});
+				});
+			} catch (err) {
+				// eslint-disable-next-line no-console
+				console.error(`Failed to send content to discord transport`, err);
+			}
+		}
+
+		// don't bother waiting around.
+		cb();
+	}
+
+	private GetWhoToTag() {
+		return ServerConfig.DISCORD_WHO_TO_TAG
+			? ServerConfig.DISCORD_WHO_TO_TAG.map((e) => `<@${e}>`).join(" ")
+			: "Nobody configured to tag, but this is bad, get someone!";
+	}
+
+	private async SendToDiscord(webhookLocation: string, info: any) {
+		const postBody = {
+			content: "",
+			embeds: [
+				{
+					description: `[${info.level}] ${info.message}`,
+					// it's Colour!!
+					color: DiscordColours[info.level as keyof typeof DiscordColours],
+					timestamp: new Date().toISOString(),
+				},
+			],
+		};
+
+		if (info.meta) {
+			postBody.content = `\`\`\`${SafeJSONStringify(info.meta, null, 4)}\`\`\``;
+		}
+
+		// These two levels are bad, and require near-immediate attention.
+
+		if (info.level === "severe") {
+			postBody.content = `SEVERE ERROR: ${this.GetWhoToTag()}\n${postBody.content}`;
+		}
+
+		if (info.level === "crit") {
+			postBody.content = `CRITICAL ERROR: ${this.GetWhoToTag()}\n${postBody.content}`;
+		}
+
+		await this.POSTData(postBody);
+	}
+
+	private async POSTData(postBody: unknown, scaleRetryDebounce = 2) {
+		const res = await fetch(this.webhookUrl, {
+			method: "POST",
+			body: JSON.stringify(postBody),
+			headers: {
+				"Content-Type": "application/json",
+			},
+		});
+
+		if (res.status === 429) {
+			// being rate limited.
+			const content = await res.json();
+
+			// Try and retry when they say so. The issue is that our logging
+			// is very async, and this is a billion race conditions.
+			// It's possible that messages here could all get stuck in an
+			// awful loop, so we have a tuning off parameter.
+			// The scaleRetryDebouncer will get squared every call,
+			// so the initial request takes 2 * (generally 1milisecond),
+			// then following requests will take even longer...
+			// It's possible this might blow up in our face.
+			// We'll have to see. - zkldi 2021/09/17
+
+			if (content.retry_after) {
+				setTimeout(() => {
+					this.POSTData(postBody, scaleRetryDebounce ** 2);
+				}, content.retry_after * scaleRetryDebounce);
+			}
+		} else if (!res.ok) {
+			// eslint-disable-next-line no-console
+			console.error(`Failed to send to discord ${res.status} ${await res.text()}`);
+		}
+	}
+}
diff --git a/server/src/lib/logger/logger.test.ts b/server/src/lib/logger/logger.test.ts
index 58c16ff5f..aebb17a6a 100644
--- a/server/src/lib/logger/logger.test.ts
+++ b/server/src/lib/logger/logger.test.ts
@@ -32,6 +32,7 @@ t.test("#GetLogLevel", (t) => {
 	t.equal(GetLogLevel(), "crit");
 
 	ChangeRootLogLevel(LOG_LEVEL);
+	t.equal(GetLogLevel(), LOG_LEVEL);
 
 	t.end();
 });
diff --git a/server/src/lib/logger/logger.ts b/server/src/lib/logger/logger.ts
index bb89fbf12..eb73f86c1 100644
--- a/server/src/lib/logger/logger.ts
+++ b/server/src/lib/logger/logger.ts
@@ -2,13 +2,12 @@ import winston, { format, transports, Logger, LeveledLogMethod } from "winston";
 import { EscapeStringRegexp } from "utils/misc";
 import SafeJSONStringify from "safe-json-stringify";
 import { ServerConfig } from "lib/setup/config";
+import CreateDiscordWinstonTransport from "./discord-transport";
 
 export type KtLogger = Logger & { severe: LeveledLogMethod };
 
 const level = process.env.LOG_LEVEL ?? ServerConfig.LOG_LEVEL;
 
-const IN_TESTING = process.env.NODE_ENV === "test";
-
 const formatExcessProperties = (meta: Record<string, unknown>) => {
 	let i = 0;
 	for (const key in meta) {
@@ -98,10 +97,7 @@ const consoleFormatRoute = format.combine(
 	})
 );
 
-const tports: (
-	| winston.transports.ConsoleTransportInstance
-	| winston.transports.FileTransportInstance
-)[] = [
+const tports: winston.transport[] = [
 	new transports.File({
 		filename: "logs/tachi-error.log",
 		level: "error",
@@ -118,6 +114,15 @@ if (!ServerConfig.NO_CONSOLE) {
 	);
 }
 
+if (ServerConfig.LOGGER_DISCORD_WEBHOOK) {
+	tports.push(
+		new CreateDiscordWinstonTransport({
+			webhook: ServerConfig.LOGGER_DISCORD_WEBHOOK,
+			level: "warn",
+		})
+	);
+}
+
 export const rootLogger = winston.createLogger({
 	levels: {
 		crit: 0, // entire process termination is necessary
@@ -133,6 +138,10 @@ export const rootLogger = winston.createLogger({
 	transports: tports,
 });
 
+if (ServerConfig.LOGGER_DISCORD_WEBHOOK) {
+	rootLogger.info(`Discord logging enabled.`);
+}
+
 function CreateLogCtx(filename: string, lg = rootLogger): KtLogger {
 	const replacedFilename = filename.replace(
 		new RegExp(`^${EscapeStringRegexp(process.cwd())}/((js|src)/)?`, "u"),
diff --git a/server/src/lib/setup/config.ts b/server/src/lib/setup/config.ts
index 7491a2060..19c41e06c 100644
--- a/server/src/lib/setup/config.ts
+++ b/server/src/lib/setup/config.ts
@@ -75,6 +75,8 @@ export interface TachiConfig {
 	USC_QUEUE_SIZE: integer;
 	BEATORAJA_QUEUE_SIZE: integer;
 	OUR_URL: string;
+	LOGGER_DISCORD_WEBHOOK?: string;
+	DISCORD_WHO_TO_TAG?: string[];
 }
 
 const isValidOauth2 = p.optional({
@@ -113,6 +115,8 @@ const err = p(config, {
 	USC_QUEUE_SIZE: p.optional(p.gteInt(2)),
 	BEATORAJA_QUEUE_SIZE: p.optional(p.gteInt(2)),
 	OUR_URL: "string",
+	LOGGER_DISCORD_WEBHOOK: "*string",
+	DISCORD_WHO_TO_TAG: p.optional(["string"]),
 });
 
 if (err) {