diff --git a/Dockerfile b/Dockerfile
index b470299f41d2d4cf7a6b66ea37036e93a2af2b6b..c814cb25de3fa663d027a207ff8d08ed6052ebb6 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -107,9 +107,13 @@ ENV PORT 3000
 ENV NODE_ENV production
 ENV SERVE_CLIENT /home/node/app/packages/client
 ENV SERVE_ADMIN /home/node/app/packages/admin
+ENV PIXEL_LOG_PATH /home/node/app/pixel.log
+
+VOLUME /home/node/app/pixel.log
 
 EXPOSE 3000
 # profiler port, only used if profiler is explicity running
 EXPOSE 9229
+
 ENTRYPOINT [ "/bin/sh" ]
 CMD [ "./docker-start.sh" ]
\ No newline at end of file
diff --git a/packages/server/src/api/admin.ts b/packages/server/src/api/admin.ts
index b3a75f5a91443edac35f5dadaba4ac8aa8ed2080..eb101a4296bd03f96cf296d12a4f6334ea058416 100644
--- a/packages/server/src/api/admin.ts
+++ b/packages/server/src/api/admin.ts
@@ -11,6 +11,7 @@ import {
   InstanceNotFound,
 } from "../models/Instance";
 import { AuditLog } from "../models/AuditLog";
+import { LogMan } from "../lib/LogMan";
 
 const app = Router();
 const Logger = getLogger("HTTP/ADMIN");
@@ -50,6 +51,25 @@ app.get("/check", (req, res) => {
   res.send({ success: true });
 });
 
+// TODO: Delete before merge
+app.get("/log", (req, res) => {
+  const user = "grant@grants.cafe";
+
+  for (let i = 0; i < 100; i++) {
+    LogMan.log("pixel_place", user, { x: 0, y: 0, hex: "ABC123" });
+    LogMan.log("pixel_undo", user, { x: 0, y: 0, hex: "FFFFFF" });
+    LogMan.log("mod_fill", user, { from: [0, 0], to: [1, 1], hex: "000000" });
+    LogMan.log("mod_override", user, { x: 0, y: 0, hex: "111111" });
+    LogMan.log("mod_rollback", user, { x: 0, y: 0, hex: "222222" });
+    LogMan.log("mod_rollback_undo", user, { x: 0, y: 0, hex: "333333" });
+    LogMan.log("canvas_size", { width: 100, height: 100 });
+    LogMan.log("canvas_freeze", {});
+    LogMan.log("canvas_unfreeze", {});
+  }
+
+  res.send("ok");
+});
+
 app.get("/canvas/size", async (req, res) => {
   const config = Canvas.getCanvasConfig();
 
@@ -86,6 +106,11 @@ app.post("/canvas/size", async (req, res) => {
   }
 
   await Canvas.setSize(width, height);
+
+  // we log this here because Canvas#setSize is ran at launch
+  // this is currently the only way the size is changed is via the API
+  LogMan.log("canvas_size", { width, height });
+
   const user = (await User.fromAuthSession(req.session.user!))!;
   const auditLog = AuditLog.Factory(user.sub)
     .doing("CANVAS_SIZE")
@@ -111,6 +136,9 @@ app.get("/canvas/freeze", async (req, res) => {
 app.post("/canvas/freeze", async (req, res) => {
   await Canvas.setFrozen(true);
 
+  // same reason as canvas size changes, we log this here because #setFrozen is ran at startup
+  LogMan.log("canvas_freeze", {});
+
   const user = (await User.fromAuthSession(req.session.user!))!;
   const auditLog = AuditLog.Factory(user.sub)
     .doing("CANVAS_FREEZE")
@@ -129,6 +157,9 @@ app.post("/canvas/freeze", async (req, res) => {
 app.delete("/canvas/freeze", async (req, res) => {
   await Canvas.setFrozen(false);
 
+  // same reason as canvas size changes, we log this here because #setFrozen is ran at startup
+  LogMan.log("canvas_unfreeze", {});
+
   const user = (await User.fromAuthSession(req.session.user!))!;
   const auditLog = AuditLog.Factory(user.sub)
     .doing("CANVAS_UNFREEZE")
@@ -272,6 +303,13 @@ app.put("/canvas/undo", async (req, res) => {
             ? paletteColors.find((p) => p.hex === coveredPixel.color)?.id || -1
             : -1,
         });
+
+        // TODO: this spams the log, it would be nicer if it combined
+        LogMan.log("mod_rollback", user_sub, {
+          x: pixel.pixel.x,
+          y: pixel.pixel.y,
+          hex: coveredPixel?.color,
+        });
         break;
       }
       case "rejected":
diff --git a/packages/server/src/index.ts b/packages/server/src/index.ts
index 0a354d3fd7ee4119c3a84f9f2e1170d4cfbf4e12..7a9fcddc0e02e41b13b0cba6a98c0b948de7af98 100644
--- a/packages/server/src/index.ts
+++ b/packages/server/src/index.ts
@@ -81,6 +81,10 @@ if (!process.env.INHIBIT_LOGIN) {
   }
 }
 
+if (!process.env.PIXEL_LOG_PATH) {
+  Logger.warn("PIXEL_LOG_PATH is not defined, defaulting to packages/server");
+}
+
 // run startup tasks, all of these need to be completed to serve
 Promise.all([
   Redis.getClient(),
diff --git a/packages/server/src/lib/Canvas.ts b/packages/server/src/lib/Canvas.ts
index d89af57f1c90123669b58152b6e5ace49a095fa4..9f0aaa71e6d040739698b6ea0881edf44a0052b8 100644
--- a/packages/server/src/lib/Canvas.ts
+++ b/packages/server/src/lib/Canvas.ts
@@ -5,6 +5,7 @@ import { SocketServer } from "./SocketServer";
 import { getLogger } from "./Logger";
 import { Pixel } from "@prisma/client";
 import { CanvasWorker } from "../workers/worker";
+import { LogMan } from "./LogMan";
 
 const Logger = getLogger("CANVAS");
 
@@ -182,7 +183,7 @@ class Canvas {
           x: pixel.x,
           y: pixel.y,
           createdAt: { lt: pixel.createdAt },
-          deletedAt: null,
+          deletedAt: null, // undone pixels will have this set
         },
         orderBy: { createdAt: "desc" },
         take: 1,
@@ -198,6 +199,11 @@ class Canvas {
       });
     }
 
+    LogMan.log("pixel_undo", pixel.userId, {
+      x: pixel.x,
+      y: pixel.y,
+      hex: coveringPixel?.color,
+    });
     return coveringPixel;
   }
 
@@ -392,6 +398,8 @@ class Canvas {
         hex,
       }))
     );
+
+    LogMan.log("mod_fill", user.sub, { from: start, to: end, hex });
   }
 
   async setPixel(
@@ -430,6 +438,11 @@ class Canvas {
     await this.updateCanvasRedisAtPos(x, y);
 
     Logger.info(`${user.sub} placed pixel at (${x}, ${y})`);
+    LogMan.log(isModAction ? "mod_override" : "pixel_place", user.sub, {
+      x,
+      y,
+      hex,
+    });
   }
 
   /**
diff --git a/packages/server/src/lib/LogMan.ts b/packages/server/src/lib/LogMan.ts
new file mode 100644
index 0000000000000000000000000000000000000000..3bfec0f26ceee52d48ebdf9edcb5d457bc56b6c0
--- /dev/null
+++ b/packages/server/src/lib/LogMan.ts
@@ -0,0 +1,85 @@
+import { PixelLogger } from "./Logger";
+
+interface UserEvents {
+  pixel_place: { x: number; y: number; hex: string };
+  pixel_undo: { x: number; y: number; hex?: string };
+  mod_fill: {
+    from: [x: number, y: number];
+    to: [x: number, y: number];
+    hex: string;
+  };
+  mod_override: { x: number; y: number; hex: string };
+  mod_rollback: { x: number; y: number; hex?: string };
+  mod_rollback_undo: { x: number; y: number; hex?: string };
+}
+
+interface SystemEvents {
+  canvas_size: { width: number; height: number };
+  canvas_freeze: {};
+  canvas_unfreeze: {};
+}
+
+/**
+ * Handle logs that should be written to a text file
+ *
+ * This could be used as an EventEmitter in the future, but as of right now
+ * it just adds typing to logging of these events
+ *
+ * TODO: better name, this one is not it
+ *
+ * @see #57
+ */
+class LogMan_ {
+  log<EventName extends keyof SystemEvents>(
+    event: EventName,
+    data: SystemEvents[EventName]
+  ): void;
+  log<EventName extends keyof UserEvents>(
+    event: EventName,
+    user: string,
+    data: UserEvents[EventName]
+  ): void;
+  log<EventName extends keyof UserEvents | keyof SystemEvents>(
+    event: EventName,
+    ...params: EventName extends keyof UserEvents
+      ? [user: string, data: UserEvents[EventName]]
+      : EventName extends keyof SystemEvents
+        ? [data: SystemEvents[EventName]]
+        : never
+  ): void {
+    let parts: string[] = [];
+
+    if (params.length === 2) {
+      // user event
+      let user = params[0] as string;
+      parts.push(user, event);
+
+      if (event === "mod_fill") {
+        // this event format has a different line format
+        let data: UserEvents["mod_fill"] = params[1] as any;
+
+        parts.push(data.from.join(","), data.to.join(","), data.hex);
+      } else {
+        let data: UserEvents[Exclude<keyof UserEvents, "mod_fill">] =
+          params[1] as any;
+        parts.push(...[data.x, data.y, data.hex || "unset"].map((a) => a + ""));
+      }
+    } else {
+      // system event
+
+      parts.push("system", event);
+
+      switch (event) {
+        case "canvas_size":
+          let data: SystemEvents["canvas_size"] = params[0] as any;
+          let { width, height } = data;
+          parts.push(width + "", height + "");
+          break;
+      }
+    }
+
+    PixelLogger.info(parts.join("\t"));
+  }
+}
+
+export const LogMan = new LogMan_();
diff --git a/packages/server/src/lib/Logger.ts b/packages/server/src/lib/Logger.ts
index f2ee3d2572b5d5810c39ceb1b9b78bb486380007..ec9261a5ca9a16c30567cb75d0450abc212472eb 100644
--- a/packages/server/src/lib/Logger.ts
+++ b/packages/server/src/lib/Logger.ts
@@ -1,6 +1,11 @@
 import winston, { format } from "winston";
+import path from "node:path";
 import { createEnum } from "./utils";
 
+// if PIXEL_LOG_PATH is defined, use that, otherwise default to packages/server root
+const PIXEL_LOG_PATH =
+  process.env.PIXEL_LOG_PATH || path.join(__dirname, "..", "..", "pixels.log");
+
 const formatter = format.printf((options) => {
   let maxModuleWidth = 0;
   for (const module of Object.values(LoggerType)) {
@@ -26,6 +31,18 @@ const Winston = winston.createLogger({
   transports: [new winston.transports.Console()],
 });
 
+// Used by LogMan for writing to pixels.log
+export const PixelLogger = winston.createLogger({
+  format: format.printf((options) => {
+    return [new Date().toISOString(), options.message].join("\t");
+  }),
+  transports: [
+    new winston.transports.File({
+      filename: PIXEL_LOG_PATH,
+    }),
+  ],
+});
+
 export const LoggerType = createEnum([
   "MAIN",
   "SETTINGS",
diff --git a/packages/server/src/types.ts b/packages/server/src/types.ts
index 727a6e7ed97523087ab2cf8251b51a3875751341..e7f7c3158c16a36fb79e4926ece023f0071445b3 100644
--- a/packages/server/src/types.ts
+++ b/packages/server/src/types.ts
@@ -61,6 +61,8 @@ declare global {
       ELEMENT_HOST: string;
       MATRIX_GENERAL_ALIAS: string;
 
+      PIXEL_LOG_PATH?: string;
+      
       RECAPTCHA_SITE_KEY?: string;
       RECAPTCHA_SECRET_KEY?: string;
       RECAPTCHA_PIXEL_CHANCE?: string;