diff --git a/.vscode/import_map.json b/.vscode/import_map.json
index dae2d6771a7..9a0bc7a0e0b 100644
--- a/.vscode/import_map.json
+++ b/.vscode/import_map.json
@@ -3,6 +3,7 @@
     "THIS FILE EXISTS ONLY FOR VSCODE! IT IS NOT USED AT RUNTIME": {}
   },
   "imports": {
+    "@vscode_787_hack/": "../tests/fixture_tailwind_remote_classes/",
     "$fresh/": "../",
     "twind": "https://esm.sh/twind@0.16.19",
     "twind/": "https://esm.sh/twind@0.16.19/",
diff --git a/plugins/tailwind/compiler.ts b/plugins/tailwind/compiler.ts
index f1c08e1dd1d..b2318491fb5 100644
--- a/plugins/tailwind/compiler.ts
+++ b/plugins/tailwind/compiler.ts
@@ -5,6 +5,12 @@ import cssnano from "npm:cssnano@6.0.3";
 import autoprefixer from "npm:autoprefixer@10.4.17";
 import * as path from "https://deno.land/std@0.216.0/path/mod.ts";
 import { TailwindPluginOptions } from "./types.ts";
+import {
+  createGraph,
+  type ModuleGraphJson,
+} from "https://deno.land/x/deno_graph@0.63.5/mod.ts";
+import { parseFromJson } from "https://deno.land/x/import_map@v0.18.3/mod.ts";
+import { parse as jsoncParse } from "https://deno.land/std@0.213.0/jsonc/mod.ts";
 
 const CONFIG_EXTENSIONS = ["ts", "js", "mjs"];
 
@@ -62,6 +68,39 @@ export async function initTailwind(
     return pattern;
   });
 
+  let importMap;
+  if (path.extname(config.denoJsonPath) === ".json") {
+    importMap = (await import(path.toFileUrl(config.denoJsonPath).href, {
+      with: { type: "json" },
+    })).default;
+  } else if (path.extname(config.denoJsonPath) === ".jsonc") {
+    const fileContents = Deno.readTextFileSync(config.denoJsonPath);
+    importMap = jsoncParse(fileContents);
+  } else {
+    throw Error("deno config must be either .json or .jsonc");
+  }
+  for (const plugin of config.plugins ?? []) {
+    if (plugin.location === undefined) continue;
+    // if the plugin is declared in a separate place than the project, the plugin developer should have specified a projectLocation
+    // otherwise, we assume the plugin is in the same directory as the project
+    const projectLocation = plugin.projectLocation ??
+      path.dirname(plugin.location);
+    const resolvedImportMap = await parseFromJson(
+      path.toFileUrl(config.denoJsonPath),
+      importMap,
+    );
+
+    const moduleGraph = await createGraph(plugin.location, {
+      resolve: resolvedImportMap.resolve.bind(resolvedImportMap),
+    });
+
+    for (const file of extractSpecifiers(moduleGraph, projectLocation)) {
+      const response = await fetch(file);
+      const content = await response.text();
+      tailwindConfig.content.push({ raw: content });
+    }
+  }
+
   // PostCSS types cause deep recursion
   const plugins = [
     // deno-lint-ignore no-explicit-any
@@ -76,3 +115,13 @@ export async function initTailwind(
 
   return postcss(plugins);
 }
+
+function extractSpecifiers(graph: ModuleGraphJson, projectLocation: string) {
+  return graph.modules
+    .filter((module) =>
+      (module.specifier.endsWith(".tsx") ||
+        module.specifier.endsWith(".jsx")) &&
+      module.specifier.startsWith(projectLocation)
+    )
+    .map((module) => module.specifier);
+}
diff --git a/src/server/config.ts b/src/server/config.ts
index c45513d66a0..91d6da24d0f 100644
--- a/src/server/config.ts
+++ b/src/server/config.ts
@@ -94,6 +94,7 @@ export async function getInternalFreshState(
     router: config.router,
     server: config.server ?? {},
     basePath,
+    denoJsonPath,
   };
 
   if (config.cert) {
diff --git a/src/server/types.ts b/src/server/types.ts
index 492eaf87299..227ae8c993f 100644
--- a/src/server/types.ts
+++ b/src/server/types.ts
@@ -119,6 +119,7 @@ export interface ResolvedFreshConfig {
   router?: RouterOptions;
   server: Partial<Deno.ServeTlsOptions>;
   basePath: string;
+  denoJsonPath: string;
 }
 
 export interface RouterOptions {
@@ -495,6 +496,19 @@ export interface Plugin<State = Record<string, unknown>> {
   middlewares?: PluginMiddleware<State>[];
 
   islands?: PluginIslands;
+
+  /**
+   * This should always be set to `import.meta.url`.
+   * Required if you want tailwind to scan your routes for classes.
+   */
+  location?: string;
+
+  /**
+   * If the plugin is declared in a separate place than the project root, specify the root here.
+   * This is necessary if your plugin is declared in a `src/` folder.
+   * Required if you want tailwind to scan your routes for classes, and your plugin is not in the root.
+   */
+  projectLocation?: string;
 }
 
 export interface PluginRenderContext {
diff --git a/tests/fixture_tailwind_remote_classes/basicPlugin.ts b/tests/fixture_tailwind_remote_classes/basicPlugin.ts
new file mode 100644
index 00000000000..416b264f64f
--- /dev/null
+++ b/tests/fixture_tailwind_remote_classes/basicPlugin.ts
@@ -0,0 +1,13 @@
+import type { Plugin } from "../../src/server/types.ts";
+import PluginComponent from "./components/PluginComponent.tsx";
+
+export const basicPlugin = {
+  name: "basic plugin",
+  routes: [
+    {
+      path: "routeFromPlugin",
+      component: PluginComponent,
+    },
+  ],
+  location: import.meta.url,
+} satisfies Plugin;
diff --git a/tests/fixture_tailwind_remote_classes/components/AtPluginComponent.tsx b/tests/fixture_tailwind_remote_classes/components/AtPluginComponent.tsx
new file mode 100644
index 00000000000..e954b6774b2
--- /dev/null
+++ b/tests/fixture_tailwind_remote_classes/components/AtPluginComponent.tsx
@@ -0,0 +1,3 @@
+export default function AtPluginComponent() {
+  return <div class="text-slate-500">AtPluginComponent</div>;
+}
diff --git a/tests/fixture_tailwind_remote_classes/components/JsxPluginComponent.jsx b/tests/fixture_tailwind_remote_classes/components/JsxPluginComponent.jsx
new file mode 100644
index 00000000000..0152746f146
--- /dev/null
+++ b/tests/fixture_tailwind_remote_classes/components/JsxPluginComponent.jsx
@@ -0,0 +1,3 @@
+export default function JsxPluginComponent() {
+  return <div class="text-emerald-500">JsxPluginComponent</div>;
+}
diff --git a/tests/fixture_tailwind_remote_classes/components/NestedPluginComponent.tsx b/tests/fixture_tailwind_remote_classes/components/NestedPluginComponent.tsx
new file mode 100644
index 00000000000..2d22b070432
--- /dev/null
+++ b/tests/fixture_tailwind_remote_classes/components/NestedPluginComponent.tsx
@@ -0,0 +1,3 @@
+export default function NestedPluginComponent() {
+  return <div class="text-amber-500">NestedPluginComponent</div>;
+}
diff --git a/tests/fixture_tailwind_remote_classes/components/PluginComponent.tsx b/tests/fixture_tailwind_remote_classes/components/PluginComponent.tsx
new file mode 100644
index 00000000000..a6767f79933
--- /dev/null
+++ b/tests/fixture_tailwind_remote_classes/components/PluginComponent.tsx
@@ -0,0 +1,3 @@
+export default function PluginComponent() {
+  return <div class="text-purple-500">PluginComponent</div>;
+}
diff --git a/tests/fixture_tailwind_remote_classes/components/VeryNestedPluginComponent.tsx b/tests/fixture_tailwind_remote_classes/components/VeryNestedPluginComponent.tsx
new file mode 100644
index 00000000000..f3407e830ba
--- /dev/null
+++ b/tests/fixture_tailwind_remote_classes/components/VeryNestedPluginComponent.tsx
@@ -0,0 +1,3 @@
+export default function VeryNestedPluginComponent() {
+  return <div class="text-cyan-500">VeryNestedPluginComponent</div>;
+}
diff --git a/tests/fixture_tailwind_remote_classes/deno.json b/tests/fixture_tailwind_remote_classes/deno.json
new file mode 100644
index 00000000000..893c73e74f7
--- /dev/null
+++ b/tests/fixture_tailwind_remote_classes/deno.json
@@ -0,0 +1,18 @@
+{
+  "lock": false,
+  "tasks": {
+    "start": "deno run -A --watch=static/,routes/ dev.ts"
+  },
+  "imports": {
+    "$fresh/": "../../",
+    "preact": "https://esm.sh/preact@10.15.1",
+    "preact/": "https://esm.sh/preact@10.15.1/",
+    "tailwindcss": "npm:tailwindcss@3.3.5",
+    "$std/": "https://deno.land/std@0.216.0/",
+    "@vscode_787_hack/": "./"
+  },
+  "compilerOptions": {
+    "jsx": "react-jsx",
+    "jsxImportSource": "preact"
+  }
+}
diff --git a/tests/fixture_tailwind_remote_classes/dev.ts b/tests/fixture_tailwind_remote_classes/dev.ts
new file mode 100755
index 00000000000..1fe3e340282
--- /dev/null
+++ b/tests/fixture_tailwind_remote_classes/dev.ts
@@ -0,0 +1,6 @@
+#!/usr/bin/env -S deno run -A --watch=static/,routes/
+
+import dev from "$fresh/dev.ts";
+import config from "./fresh.config.ts";
+
+await dev(import.meta.url, "./main.ts", config);
diff --git a/tests/fixture_tailwind_remote_classes/fresh.config.ts b/tests/fixture_tailwind_remote_classes/fresh.config.ts
new file mode 100644
index 00000000000..53f9f1da0ff
--- /dev/null
+++ b/tests/fixture_tailwind_remote_classes/fresh.config.ts
@@ -0,0 +1,18 @@
+import { defineConfig, Plugin } from "$fresh/server.ts";
+import tailwind from "$fresh/plugins/tailwind.ts";
+import { basicPlugin } from "./basicPlugin.ts";
+import { nestedPlugin } from "./nestedPlugins/nestedPlugin.ts";
+import { hackyRemotePlugin } from "https://raw.githubusercontent.com/denoland/fresh/727d0e729e154323b99b319c04f9805f382949f0/tests/fixture_tailwind_remote_classes/hackyRemotePlugin.tsx";
+import { veryNestedPlugin } from "./nestedPlugins/nested/nested/nested/veryNestedPlugin.ts";
+import { jsxPlugin } from "./jsxPlugin.ts";
+
+export default defineConfig({
+  plugins: [
+    tailwind(),
+    basicPlugin,
+    nestedPlugin,
+    hackyRemotePlugin as Plugin,
+    veryNestedPlugin,
+    jsxPlugin,
+  ],
+});
diff --git a/tests/fixture_tailwind_remote_classes/fresh.gen.ts b/tests/fixture_tailwind_remote_classes/fresh.gen.ts
new file mode 100644
index 00000000000..2e895a65907
--- /dev/null
+++ b/tests/fixture_tailwind_remote_classes/fresh.gen.ts
@@ -0,0 +1,21 @@
+// DO NOT EDIT. This file is generated by Fresh.
+// This file SHOULD be checked into source version control.
+// This file is automatically updated during development when running `dev.ts`.
+
+import * as $_app from "./routes/_app.tsx";
+import * as $_middleware from "./routes/_middleware.ts";
+import * as $index from "./routes/index.tsx";
+
+import { type Manifest } from "$fresh/server.ts";
+
+const manifest = {
+  routes: {
+    "./routes/_app.tsx": $_app,
+    "./routes/_middleware.ts": $_middleware,
+    "./routes/index.tsx": $index,
+  },
+  islands: {},
+  baseUrl: import.meta.url,
+} satisfies Manifest;
+
+export default manifest;
diff --git a/tests/fixture_tailwind_remote_classes/jsxPlugin.ts b/tests/fixture_tailwind_remote_classes/jsxPlugin.ts
new file mode 100644
index 00000000000..95fd2a02643
--- /dev/null
+++ b/tests/fixture_tailwind_remote_classes/jsxPlugin.ts
@@ -0,0 +1,13 @@
+import type { Plugin } from "../../src/server/types.ts";
+import JsxPluginComponent from "./components/JsxPluginComponent.jsx";
+
+export const jsxPlugin = {
+  name: "jsx plugin",
+  routes: [
+    {
+      path: "routeFromJsxPlugin",
+      component: JsxPluginComponent,
+    },
+  ],
+  location: import.meta.url,
+} satisfies Plugin;
diff --git a/tests/fixture_tailwind_remote_classes/main.ts b/tests/fixture_tailwind_remote_classes/main.ts
new file mode 100644
index 00000000000..fc9359215e3
--- /dev/null
+++ b/tests/fixture_tailwind_remote_classes/main.ts
@@ -0,0 +1,11 @@
+/// <reference no-default-lib="true" />
+/// <reference lib="dom" />
+/// <reference lib="dom.iterable" />
+/// <reference lib="dom.asynciterable" />
+/// <reference lib="deno.ns" />
+
+import { start } from "$fresh/server.ts";
+import manifest from "./fresh.gen.ts";
+import config from "./fresh.config.ts";
+
+await start(manifest, config);
diff --git a/tests/fixture_tailwind_remote_classes/nestedPlugins/nested/nested/nested/veryNestedPlugin.ts b/tests/fixture_tailwind_remote_classes/nestedPlugins/nested/nested/nested/veryNestedPlugin.ts
new file mode 100644
index 00000000000..fdf10606bb7
--- /dev/null
+++ b/tests/fixture_tailwind_remote_classes/nestedPlugins/nested/nested/nested/veryNestedPlugin.ts
@@ -0,0 +1,13 @@
+import { normalize } from "$std/url/normalize.ts";
+import type { Plugin } from "../../../../../../src/server/types.ts";
+import VeryNestedPluginComponent from "../../../../components/VeryNestedPluginComponent.tsx";
+
+export const veryNestedPlugin = {
+  name: "very nested plugin",
+  location: import.meta.url,
+  projectLocation: normalize(import.meta.url + "../../../../../../").href,
+  routes: [{
+    path: "routeFromVeryNestedPlugin",
+    component: VeryNestedPluginComponent,
+  }],
+} satisfies Plugin;
diff --git a/tests/fixture_tailwind_remote_classes/nestedPlugins/nestedPlugin.ts b/tests/fixture_tailwind_remote_classes/nestedPlugins/nestedPlugin.ts
new file mode 100644
index 00000000000..1c87312cbd6
--- /dev/null
+++ b/tests/fixture_tailwind_remote_classes/nestedPlugins/nestedPlugin.ts
@@ -0,0 +1,17 @@
+import { normalize } from "$std/url/normalize.ts";
+import type { Plugin } from "../../../src/server/types.ts";
+import NestedPluginComponent from "../components/NestedPluginComponent.tsx";
+import AtPluginComponent from "@vscode_787_hack/components/AtPluginComponent.tsx";
+
+export const nestedPlugin = {
+  name: "nested plugin",
+  location: import.meta.url,
+  projectLocation: normalize(import.meta.url + "../../../").href,
+  routes: [{
+    path: "routeFromNestedPlugin",
+    component: NestedPluginComponent,
+  }, {
+    path: "atRouteFromNestedPlugin",
+    component: AtPluginComponent,
+  }],
+} satisfies Plugin;
diff --git a/tests/fixture_tailwind_remote_classes/routes/_app.tsx b/tests/fixture_tailwind_remote_classes/routes/_app.tsx
new file mode 100644
index 00000000000..2e225e497f4
--- /dev/null
+++ b/tests/fixture_tailwind_remote_classes/routes/_app.tsx
@@ -0,0 +1,17 @@
+import { PageProps } from "$fresh/server.ts";
+
+export default function App({ Component }: PageProps) {
+  return (
+    <html>
+      <head>
+        <meta charset="utf-8" />
+        <meta name="viewport" content="width=device-width, initial-scale=1.0" />
+        <title>My Fresh app</title>
+        <link rel="stylesheet" href="/styles.css" />
+      </head>
+      <body>
+        <Component />
+      </body>
+    </html>
+  );
+}
diff --git a/tests/fixture_tailwind_remote_classes/routes/_middleware.ts b/tests/fixture_tailwind_remote_classes/routes/_middleware.ts
new file mode 100644
index 00000000000..362a96be86b
--- /dev/null
+++ b/tests/fixture_tailwind_remote_classes/routes/_middleware.ts
@@ -0,0 +1,15 @@
+import { FreshContext } from "$fresh/server.ts";
+
+export async function handler(
+  _req: Request,
+  ctx: FreshContext,
+) {
+  if (ctx.url.pathname === "/middleware-only.css") {
+    return new Response(".foo-bar { color: red }", {
+      headers: {
+        "Content-Type": "text/css",
+      },
+    });
+  }
+  return await ctx.next();
+}
diff --git a/tests/fixture_tailwind_remote_classes/routes/index.tsx b/tests/fixture_tailwind_remote_classes/routes/index.tsx
new file mode 100644
index 00000000000..ee3f8f3c9bd
--- /dev/null
+++ b/tests/fixture_tailwind_remote_classes/routes/index.tsx
@@ -0,0 +1,3 @@
+export default function Page() {
+  return <h1 class="text-red-600 block">foo</h1>;
+}
diff --git a/tests/fixture_tailwind_remote_classes/static/styles.css b/tests/fixture_tailwind_remote_classes/static/styles.css
new file mode 100644
index 00000000000..b5c61c95671
--- /dev/null
+++ b/tests/fixture_tailwind_remote_classes/static/styles.css
@@ -0,0 +1,3 @@
+@tailwind base;
+@tailwind components;
+@tailwind utilities;
diff --git a/tests/fixture_tailwind_remote_classes/tailwind.config.ts b/tests/fixture_tailwind_remote_classes/tailwind.config.ts
new file mode 100644
index 00000000000..431b1c75e81
--- /dev/null
+++ b/tests/fixture_tailwind_remote_classes/tailwind.config.ts
@@ -0,0 +1,7 @@
+import { Config } from "tailwindcss";
+
+export default {
+  content: [
+    "{routes,islands}/**/*.{ts,tsx}", // deliberately ignore components
+  ],
+} satisfies Config;
diff --git a/tests/main_test.ts b/tests/main_test.ts
index 259b8669859..8d07a81029a 100644
--- a/tests/main_test.ts
+++ b/tests/main_test.ts
@@ -1142,6 +1142,7 @@ Deno.test("Expose config in ctx", async () => {
             "safari15",
           ],
         },
+        denoJsonPath: join(Deno.cwd(), "tests", "fixture", "deno.json"),
         dev: false,
         plugins: [],
         render: "Function",
@@ -1191,6 +1192,7 @@ Deno.test("Expose config in ctx", async () => {
             "safari15",
           ],
         },
+        denoJsonPath: join(Deno.cwd(), "tests", "fixture", "deno.json"),
         dev: false,
         plugins: [],
         render: "Function",
diff --git a/tests/server_components_test.ts b/tests/server_components_test.ts
index a32cac6539a..9a8ead2fc75 100644
--- a/tests/server_components_test.ts
+++ b/tests/server_components_test.ts
@@ -1,4 +1,4 @@
-import { assertEquals } from "./deps.ts";
+import { assertEquals, join } from "./deps.ts";
 import {
   assertSelector,
   assertTextMany,
@@ -93,6 +93,12 @@ Deno.test("passes context to server component", async () => {
                 "safari15",
               ],
             },
+            denoJsonPath: join(
+              Deno.cwd(),
+              "tests",
+              "fixture_server_components",
+              "deno.json",
+            ),
             dev: false,
             plugins: [
               { entrypoints: {}, name: "twind", renderAsync: "AsyncFunction" },
diff --git a/tests/tailwind_test.ts b/tests/tailwind_test.ts
index ad7b785102a..33b1012260e 100644
--- a/tests/tailwind_test.ts
+++ b/tests/tailwind_test.ts
@@ -122,3 +122,64 @@ Deno.test("TailwindCSS - missing snapshot on Deno Deploy", async () => {
     },
   );
 });
+
+Deno.test("TailwindCSS remote classes - dev mode", async () => {
+  await withFakeServe(
+    "./tests/fixture_tailwind_remote_classes/dev.ts",
+    async (server) => {
+      const res = await server.get("/styles.css");
+      const content = await res.text();
+      assertStringIncludes(content, ".text-purple-500"); //PluginComponent
+      assertStringIncludes(content, ".text-amber-500"); //NestedPluginComponent
+      assertStringIncludes(content, ".text-slate-500"); //AtPluginComponent
+      assertStringIncludes(content, ".text-lime-500"); //HackyPluginComponent
+      assertStringIncludes(content, ".text-cyan-500"); //VeryNestedPluginComponent
+      assertStringIncludes(content, ".text-emerald-500"); //JsxComponent
+    },
+    { loadConfig: true },
+  );
+});
+
+Deno.test("TailwindCSS remote classes - dev mode jsonc", async () => {
+  const originalPath = "./tests/fixture_tailwind_remote_classes/deno.json";
+  const newPath = "./tests/fixture_tailwind_remote_classes/deno.jsonc";
+
+  await Deno.rename(originalPath, newPath);
+
+  try {
+    await withFakeServe(
+      "./tests/fixture_tailwind_remote_classes/dev.ts",
+      async (server) => {
+        const res = await server.get("/styles.css");
+        const content = await res.text();
+        assertStringIncludes(content, ".text-purple-500"); // PluginComponent
+        assertStringIncludes(content, ".text-amber-500"); // NestedPluginComponent
+        assertStringIncludes(content, ".text-slate-500"); // AtPluginComponent
+        assertStringIncludes(content, ".text-lime-500"); // HackyPluginComponent
+        assertStringIncludes(content, ".text-cyan-500"); // VeryNestedPluginComponent
+        assertStringIncludes(content, ".text-emerald-500"); // JsxComponent
+      },
+      { loadConfig: true },
+    );
+  } finally {
+    await Deno.rename(newPath, originalPath);
+  }
+});
+
+Deno.test("TailwindCSS remote classes - build mode", async () => {
+  await runBuild("./tests/fixture_tailwind_remote_classes/dev.ts");
+  await withFakeServe(
+    "./tests/fixture_tailwind_remote_classes/main.ts",
+    async (server) => {
+      const res = await server.get("/styles.css");
+      const content = await res.text();
+      assertStringIncludes(content, ".text-purple-500"); //PluginComponent
+      assertStringIncludes(content, ".text-amber-500"); //NestedPluginComponent
+      assertStringIncludes(content, ".text-slate-500"); //AtPluginComponent
+      assertStringIncludes(content, ".text-lime-500"); //HackyPluginComponent
+      assertStringIncludes(content, ".text-cyan-500"); //VeryNestedPluginComponent
+      assertStringIncludes(content, ".text-emerald-500"); //JsxComponent
+    },
+    { loadConfig: true },
+  );
+});