diff --git a/nuxt.config.ts b/nuxt.config.ts
index b531bcd..96b9415 100644
--- a/nuxt.config.ts
+++ b/nuxt.config.ts
@@ -1,6 +1,6 @@
 import tailwindcss from "@tailwindcss/vite";
 
-const dropVersion = "0.3";
+const dropVersion = "v0.3.0";
 
 // https://nuxt.com/docs/api/configuration/nuxt-config
 export default defineNuxtConfig({
diff --git a/package.json b/package.json
index 398a063..b9a52f9 100644
--- a/package.json
+++ b/package.json
@@ -37,6 +37,7 @@
     "nuxt": "^3.16.2",
     "nuxt-security": "2.2.0",
     "prisma": "^6.7.0",
+    "semver": "^7.7.1",
     "stream-mime-type": "^2.0.0",
     "turndown": "^7.2.0",
     "unstorage": "^1.15.0",
@@ -53,6 +54,7 @@
     "@types/bcryptjs": "^3.0.0",
     "@types/luxon": "^3.6.2",
     "@types/node": "^22.13.16",
+    "@types/semver": "^7.7.0",
     "@types/turndown": "^5.0.5",
     "autoprefixer": "^10.4.20",
     "eslint": "^9.24.0",
diff --git a/server/h3.d.ts b/server/h3.d.ts
index 76ff537..67eced1 100644
--- a/server/h3.d.ts
+++ b/server/h3.d.ts
@@ -1 +1,5 @@
 export type MinimumRequestObject = { headers: Headers };
+
+export type TaskReturn<T = unknown> =
+  | { success: true; data: T; error?: never }
+  | { success: false; data?: never; error: { message: string } };
diff --git a/server/internal/config/sys-conf.ts b/server/internal/config/sys-conf.ts
index 306d81e..560a661 100644
--- a/server/internal/config/sys-conf.ts
+++ b/server/internal/config/sys-conf.ts
@@ -1,6 +1,12 @@
 class SystemConfig {
   private libraryFolder = process.env.LIBRARY ?? "./.data/library";
   private dataFolder = process.env.DATA ?? "./.data/data";
+  private dropVersion = "v0.3.0";
+  private checkForUpdates =
+    process.env.CHECK_FOR_UPDATES !== undefined &&
+    process.env.CHECK_FOR_UPDATES.toLocaleLowerCase() === "true"
+      ? true
+      : false;
 
   getLibraryFolder() {
     return this.libraryFolder;
@@ -9,6 +15,14 @@ class SystemConfig {
   getDataFolder() {
     return this.dataFolder;
   }
+
+  getDropVersion() {
+    return this.dropVersion;
+  }
+
+  shouldCheckForUpdates() {
+    return this.checkForUpdates;
+  }
 }
 
 export const systemConfig = new SystemConfig();
diff --git a/server/internal/metadata/index.ts b/server/internal/metadata/index.ts
index f50e8e4..8721459 100644
--- a/server/internal/metadata/index.ts
+++ b/server/internal/metadata/index.ts
@@ -10,6 +10,7 @@ import type {
 } from "./types";
 import { ObjectTransactionalHandler } from "../objects/transactional";
 import { PriorityListIndexed } from "../utils/prioritylist";
+import { systemConfig } from "../config/sys-conf";
 
 export class MissingMetadataProviderConfig extends Error {
   private providerName: string;
@@ -25,7 +26,7 @@ export class MissingMetadataProviderConfig extends Error {
 }
 
 // TODO: add useragent to all outbound api calls (best practice)
-export const DropUserAgent = "Drop/0.2";
+export const DropUserAgent = `Drop/${systemConfig.getDropVersion()}`;
 
 export abstract class MetadataProvider {
   abstract name(): string;
diff --git a/server/internal/notifications/index.ts b/server/internal/notifications/index.ts
index 930f317..67570dc 100644
--- a/server/internal/notifications/index.ts
+++ b/server/internal/notifications/index.ts
@@ -9,6 +9,7 @@ Design goals:
 import type { Notification } from "~/prisma/client";
 import prisma from "../db/database";
 
+// TODO: document notification action format
 export type NotificationCreateArgs = Pick<
   Notification,
   "title" | "description" | "actions" | "nonce"
@@ -61,14 +62,18 @@ class NotificationSystem {
       throw new Error("No nonce in notificationCreateArgs");
     const notification = await prisma.notification.upsert({
       where: {
-        nonce: notificationCreateArgs.nonce,
+        userId_nonce: {
+          nonce: notificationCreateArgs.nonce,
+          userId,
+        },
       },
       update: {
-        userId: userId,
+        // we don't need to update the userid right?
+        // userId: userId,
         ...notificationCreateArgs,
       },
       create: {
-        userId: userId,
+        userId,
         ...notificationCreateArgs,
       },
     });
@@ -84,13 +89,34 @@ class NotificationSystem {
       },
     });
 
+    const res: Promise<void>[] = [];
     for (const user of users) {
-      await this.push(user.id, notificationCreateArgs);
+      res.push(this.push(user.id, notificationCreateArgs));
     }
+    // wait for all notifications to pass
+    await Promise.all(res);
   }
 
   async systemPush(notificationCreateArgs: NotificationCreateArgs) {
-    return await this.push("system", notificationCreateArgs);
+    await this.push("system", notificationCreateArgs);
+  }
+
+  async pushAllAdmins(notificationCreateArgs: NotificationCreateArgs) {
+    const users = await prisma.user.findMany({
+      where: {
+        admin: true,
+      },
+      select: {
+        id: true,
+      },
+    });
+
+    const res: Promise<void>[] = [];
+    for (const user of users) {
+      res.push(this.push(user.id, notificationCreateArgs));
+    }
+    // wait for all notifications to pass
+    await Promise.all(res);
   }
 }
 
diff --git a/server/plugins/tasks.ts b/server/plugins/tasks.ts
index 3c8dde4..a822007 100644
--- a/server/plugins/tasks.ts
+++ b/server/plugins/tasks.ts
@@ -3,5 +3,8 @@ export default defineNitroPlugin(async (_nitro) => {
   await Promise.all([
     runTask("cleanup:invitations"),
     runTask("cleanup:sessions"),
+    // TODO: maybe implement some sort of rate limit thing to prevent this from calling github api a bunch in the event of crashloop or whatever?
+    // probably will require custom task scheduler for object cleanup anyway, so something to thing about
+    runTask("check:update"),
   ]);
 });
diff --git a/server/tasks/check/update.ts b/server/tasks/check/update.ts
new file mode 100644
index 0000000..96de84d
--- /dev/null
+++ b/server/tasks/check/update.ts
@@ -0,0 +1,143 @@
+import { type } from "arktype";
+import { systemConfig } from "../../internal/config/sys-conf";
+import * as semver from "semver";
+import type { TaskReturn } from "../../h3";
+import notificationSystem from "../../internal/notifications";
+
+const latestRelease = type({
+  url: "string", // api url for specific release
+  html_url: "string", // user facing url
+  id: "number", // release id
+  tag_name: "string", // tag used for release
+  name: "string", // release name
+  draft: "boolean",
+  prerelease: "boolean",
+  created_at: "string",
+  published_at: "string",
+});
+
+export default defineTask<TaskReturn>({
+  meta: {
+    name: "check:update",
+  },
+  async run() {
+    if (systemConfig.shouldCheckForUpdates()) {
+      console.log("[Task check:update]: Checking for update");
+      try {
+        const response = await fetch(
+          "https://api.github.com/repos/Drop-OSS/drop/releases/latest",
+        );
+
+        if (!response.ok) {
+          console.log("[Task check:update]: Failed to check for update", {
+            status: response.status,
+            body: response.body,
+          });
+
+          return {
+            result: {
+              success: false,
+              error: {
+                message: "" + response.status,
+              },
+            },
+          };
+        }
+
+        const resJson = await response.json();
+        const body = latestRelease(resJson);
+        if (body instanceof type.errors) {
+          console.error(body.summary);
+          console.log("GitHub Api response", resJson);
+          return {
+            result: {
+              success: false,
+              error: {
+                message: body.summary,
+              },
+            },
+          };
+        }
+
+        // const currVerStr = systemConfig.getDropVersion()
+        const currVerStr = "v0.1";
+
+        const latestVer = semver.coerce(body.tag_name);
+        const currVer = semver.coerce(currVerStr);
+        if (latestVer === null) {
+          const msg = "Github Api returned invalid semver tag";
+          console.log("[Task check:update]:", msg);
+          return {
+            result: {
+              success: false,
+              error: {
+                message: msg,
+              },
+            },
+          };
+        } else if (currVer === null) {
+          const msg = "Drop provided a invalid semver tag";
+          console.log("[Task check:update]:", msg);
+          return {
+            result: {
+              success: false,
+              error: {
+                message: msg,
+              },
+            },
+          };
+        }
+
+        if (semver.gt(latestVer, currVer)) {
+          console.log("[Task check:update]: Update available");
+          notificationSystem.pushAllAdmins({
+            nonce: `drop-update-available-${currVer}-to-${latestVer}`,
+            title: `Update available to v${latestVer}`,
+            description: `A new version of Drop is available v${latestVer}`,
+            actions: [`View|${body.html_url}`],
+          });
+        } else {
+          console.log("[Task check:update]: no update available");
+        }
+
+        console.log("[Task check:update]: Done");
+      } catch (e) {
+        console.error(e);
+        if (typeof e === "string") {
+          return {
+            result: {
+              success: false,
+              error: {
+                message: e,
+              },
+            },
+          };
+        } else if (e instanceof Error) {
+          return {
+            result: {
+              success: false,
+              error: {
+                message: e.message,
+              },
+            },
+          };
+        }
+
+        return {
+          result: {
+            success: false,
+            error: {
+              message: "unknown cause, please check console",
+            },
+          },
+        };
+      }
+    }
+    return {
+      result: {
+        success: true,
+        data: undefined,
+      },
+    };
+  },
+});
diff --git a/yarn.lock b/yarn.lock
index 99ff8c7..634ac27 100644
--- a/yarn.lock
+++ b/yarn.lock
@@ -1830,6 +1830,11 @@
   resolved "https://registry.yarnpkg.com/@types/resolve/-/resolve-1.20.2.tgz#97d26e00cd4a0423b4af620abecf3e6f442b7975"
   integrity sha512-60BCwRFOZCQhDncwQdxxeOEEkbc5dIMccYLwbxsS4TUNeVECQ/pBJ0j09mrHOl/JJvpRPGwO9SvE4nR2Nb/a4Q==
 
+"@types/semver@^7.7.0":
+  version "7.7.0"
+  resolved "https://registry.yarnpkg.com/@types/semver/-/semver-7.7.0.tgz#64c441bdae033b378b6eef7d0c3d77c329b9378e"
+  integrity sha512-k107IF4+Xr7UHjwDc7Cfd6PRQfbdkiRabXGRjo07b4WyPahFBZCZ1sE+BNxYIJPPg73UkfOsVOLwqVc/6ETrIA==
+
 "@types/turndown@^5.0.5":
   version "5.0.5"
   resolved "https://registry.yarnpkg.com/@types/turndown/-/turndown-5.0.5.tgz#614de24fc9ace4d8c0d9483ba81dc8c1976dd26f"