diff --git a/.github/workflows/ci-bun-loaders.yml b/.github/workflows/ci-bun-loaders.yml
new file mode 100644
index 000000000..18026ada2
--- /dev/null
+++ b/.github/workflows/ci-bun-loaders.yml
@@ -0,0 +1,36 @@
+name: Continuous Integration - Bun (Loaders)
+
+on: [pull_request]
+
+jobs:
+  build:
+    runs-on: ubuntu-latest
+
+    strategy:
+      matrix:
+        node: [24]
+
+    steps:
+      - name: Clone repository
+        uses: actions/checkout@v4
+
+      # still using Yarn since we specifically rely on Yarn workspaces
+      - name: Setup Node.js ${{ matrix.node }}
+        uses: actions/setup-node@v4
+        with:
+          node-version: ${{ matrix.node }}
+
+      - name: Install Bun
+        uses: oven-sh/setup-bun@v2
+
+      - name: Disable Strict SSL
+        run: yarn config set strict-ssl false
+
+      - name: Install Dependencies
+        run: yarn install --frozen-lockfile
+
+      - name: Test
+        run: bun run --bun test:bun:loaders
+
+      - name: Build
+        run: bun run --bun build
diff --git a/.github/workflows/ci-bun.yml b/.github/workflows/ci-bun.yml
new file mode 100644
index 000000000..d0b95c1d5
--- /dev/null
+++ b/.github/workflows/ci-bun.yml
@@ -0,0 +1,37 @@
+name: Continuous Integration - Bun
+on:
+  pull_request:
+    branches: master
+
+jobs:
+  build:
+    runs-on: ubuntu-latest
+
+    strategy:
+      matrix:
+        node: [24]
+
+    steps:
+      - name: Clone repository
+        uses: actions/checkout@v4
+
+      # still using Yarn since we specifically rely on Yarn workspaces
+      - name: Setup Node.js ${{ matrix.node }}
+        uses: actions/setup-node@v4
+        with:
+          node-version: ${{ matrix.node }}
+
+      - name: Install Bun
+        uses: oven-sh/setup-bun@v2
+
+      - name: Disable Strict SSL
+        run: yarn config set strict-ssl false
+
+      - name: Install Dependencies
+        run: yarn install --frozen-lockfile
+
+      - name: Test
+        run: bun run --bun test:bun
+
+      - name: Build
+        run: bun run --bun build
diff --git a/.mocharc.cjs b/.mocharc.cjs
index 299c579d5..a394cbad8 100644
--- a/.mocharc.cjs
+++ b/.mocharc.cjs
@@ -1,3 +1,3 @@
 module.exports = {
-  timeout: 90000,
+  timeout: 540000,
 };
diff --git a/package.json b/package.json
index 96f1ef357..1fb01b9e4 100644
--- a/package.json
+++ b/package.json
@@ -22,6 +22,8 @@
     "test": "cross-env BROWSERSLIST_IGNORE_OLD_DATA=true __GWD_ROLLUP_MODE__=strict NODE_NO_WARNINGS=1 c8 mocha --exclude \"./packages/**/test/cases/loaders-*/**\" \"./packages/**/**/*.spec.js\"",
     "test:loaders": "cross-env BROWSERSLIST_IGNORE_OLD_DATA=true __GWD_ROLLUP_MODE__=strict NODE_NO_WARNINGS=1 node --import $(pwd)/test/test-register.js ./node_modules/mocha/bin/mocha \"./packages/**/**/*.spec.js\"",
     "test:loaders:win": "cross-env BROWSERSLIST_IGNORE_OLD_DATA=true __GWD_ROLLUP_MODE__=strict NODE_NO_WARNINGS=1 node --import file:\\\\%cd%\\test\\test-register.js ./node_modules/mocha/bin/mocha --exclude \"./packages/init/test/cases/**\" \"./packages/**/**/*.spec.js\"",
+    "test:bun": "cross-env BROWSERSLIST_IGNORE_OLD_DATA=true __GWD_ROLLUP_MODE__=strict NODE_NO_WARNINGS=1 mocha --exclude \"./packages/**/test/cases/loaders-*/**\" \"./packages/**/**/*.spec.js\"",
+    "test:bun:loaders": "cross-env BROWSERSLIST_IGNORE_OLD_DATA=true __GWD_ROLLUP_MODE__=strict NODE_NO_WARNINGS=1 node --import $(pwd)/test/test-register.js ./node_modules/mocha/bin/mocha \"./packages/**/**/*.spec.js\"",
     "test:tdd": "yarn test --watch",
     "lint": "yarn run lint:ls && yarn run lint:js && yarn run lint:types",
     "lint:js": "eslint",
@@ -34,6 +36,9 @@
     "format:check": "prettier . --check",
     "prepare": "husky"
   },
+  "trustedDependencies": [
+    "puppeteer"
+  ],
   "devDependencies": {
     "@babel/core": "^7.24.4",
     "@babel/eslint-parser": "^7.25.7",
diff --git a/packages/cli/src/lib/resource-utils.js b/packages/cli/src/lib/resource-utils.js
index dee4dc1f7..b2a2772a8 100644
--- a/packages/cli/src/lib/resource-utils.js
+++ b/packages/cli/src/lib/resource-utils.js
@@ -84,6 +84,10 @@ function normalizePathnameForWindows(url) {
 }
 
 async function checkResourceExists(url) {
+  if (url.pathname === "/") {
+    return false;
+  }
+
   try {
     await fs.access(url);
     return true;
diff --git a/packages/cli/src/lib/walker-package-ranger.js b/packages/cli/src/lib/walker-package-ranger.js
index b38c074f0..385946c7b 100644
--- a/packages/cli/src/lib/walker-package-ranger.js
+++ b/packages/cli/src/lib/walker-package-ranger.js
@@ -92,7 +92,7 @@ async function walkExportPatterns(dependency, condition, resolvedRoot) {
   // https://app.unpkg.com/three@0.180.0/files/package.json
   const needle = condition.endsWith("/*") ? `${condition}*` : condition;
   const matches = fs.promises.glob(needle.startsWith("/") ? needle.replace("/", "") : needle, {
-    cwd: new URL(resolvedRoot),
+    cwd: new URL(resolvedRoot).pathname,
   });
 
   for await (const match of matches) {
diff --git a/packages/cli/src/plugins/resource/plugin-active-content.js b/packages/cli/src/plugins/resource/plugin-active-content.js
index d0edaf1f7..4a573e34c 100644
--- a/packages/cli/src/plugins/resource/plugin-active-content.js
+++ b/packages/cli/src/plugins/resource/plugin-active-content.js
@@ -138,7 +138,7 @@ class ContentAsDataResource {
   async shouldOptimize(url, response) {
     const { activeContent } = this.compilation.config;
 
-    return response.headers.get("Content-Type").indexOf(this.contentType[0]) >= 0 && activeContent;
+    return response.headers.get("Content-Type")?.indexOf(this.contentType[0]) >= 0 && activeContent;
   }
 
   async optimize(url, response) {
diff --git a/packages/cli/src/plugins/resource/plugin-node-modules.js b/packages/cli/src/plugins/resource/plugin-node-modules.js
index 9c983a2f3..b3c920fef 100644
--- a/packages/cli/src/plugins/resource/plugin-node-modules.js
+++ b/packages/cli/src/plugins/resource/plugin-node-modules.js
@@ -41,17 +41,22 @@ class NodeModulesResource {
   }
 
   async shouldServe(url) {
-    const { href, protocol } = url;
+    const { href, protocol, pathname } = url;
 
-    return protocol === "file:" && (await checkResourceExists(new URL(href)));
+    return (
+      protocol === "file:" &&
+      pathname.indexOf("/node_modules/") >= 0 &&
+      (await checkResourceExists(new URL(href)))
+    );
   }
 
-  async serve(url) {
+  async serve(url, request) {
     const body = await fs.readFile(url, "utf-8");
+    const contentType = request.headers.get("content-type") ?? this.contentType;
 
     return new Response(body, {
       headers: new Headers({
-        "Content-Type": this.contentType,
+        "Content-Type": contentType,
       }),
     });
   }
diff --git a/packages/cli/test/cases/build.config.prerender-collections/build.config.prerender-collections.spec.js b/packages/cli/test/cases/build.config.prerender-collections/build.config.prerender-collections.spec.js
index bc9047bb0..e3f1e96a4 100644
--- a/packages/cli/test/cases/build.config.prerender-collections/build.config.prerender-collections.spec.js
+++ b/packages/cli/test/cases/build.config.prerender-collections/build.config.prerender-collections.spec.js
@@ -166,30 +166,38 @@ describe("Build Greenwood With: ", function () {
           expect(linkItems.length).to.equal(2);
         });
 
+        // we _technically_ can't assume the order of pages but we can at least make sure all the files are there
+        // this could easily be solved by adding an `order` property to the page's frontmatter
+        // https://github.com/ProjectEvergreen/greenwood/pull/1308#issuecomment-3368603613
         it("should have the expected link content from all pages in the collection", function () {
-          expect(linkItems[0].getAttribute("href")).to.equal("/blog/");
-          expect(linkItems[0].getAttribute("title")).to.equal("Blog");
-          expect(linkItems[0].textContent).to.equal("Blog");
+          const blogLink = Array.from(linkItems).find(
+            (link) => link.getAttribute("href") === "/blog/",
+          );
+          const tocLink = Array.from(linkItems).find(
+            (link) => link.getAttribute("href") === "/toc/",
+          );
 
-          expect(linkItems[1].getAttribute("href")).to.equal("/toc/");
-          expect(linkItems[1].getAttribute("title")).to.equal("Table of Contents");
-          expect(linkItems[1].textContent).to.equal("Table of Contents");
+          expect(blogLink.getAttribute("title")).to.equal("Blog");
+          expect(blogLink.textContent).to.equal("Blog");
+
+          expect(tocLink.getAttribute("title")).to.equal("Table of Contents");
+          expect(tocLink.textContent).to.equal("Table of Contents");
         });
 
         it("should have the expected inline active frontmatter collection data", function () {
           const collection = JSON.parse(
             dom.window.document.querySelector("body span#footer").textContent,
           );
+          const blogItem = collection.find((page) => page.route === "/blog/");
+          const tocItem = collection.find((page) => page.route === "/toc/");
 
-          expect(collection[0].route).to.equal("/blog/");
-          expect(collection[0].title).to.equal("Blog");
-          expect(collection[0].label).to.equal(collection[0].title);
-          expect(collection[0].id).to.equal("blog-index");
+          expect(blogItem.title).to.equal("Blog");
+          expect(blogItem.label).to.equal("Blog");
+          expect(blogItem.id).to.equal("blog-index");
 
-          expect(collection[1].route).to.equal("/toc/");
-          expect(collection[1].title).to.equal("Table of Contents");
-          expect(collection[1].label).to.equal(collection[1].title);
-          expect(collection[1].id).to.equal("toc");
+          expect(tocItem.title).to.equal("Table of Contents");
+          expect(tocItem.label).to.equal("Table of Contents");
+          expect(tocItem.id).to.equal("toc");
         });
       });
     });
@@ -212,14 +220,22 @@ describe("Build Greenwood With: ", function () {
           expect(postLinks.length).to.equal(2);
         });
 
+        // we _technically_ can't assume the order of pages but we can at least make sure all the files are there
+        // this could easily be solved by adding an `order` property to the page's frontmatter
+        // https://github.com/ProjectEvergreen/greenwood/pull/1308#issuecomment-3368603613
         it("should have the expected link content from all pages in the collection", function () {
-          expect(postLinks[0].getAttribute("href")).to.equal("/blog/first-post/");
-          expect(postLinks[0].getAttribute("title")).to.equal("First Post");
-          expect(postLinks[0].textContent).to.equal("First Post");
+          const firstPostLink = Array.from(postLinks).find(
+            (link) => link.getAttribute("href") === "/blog/first-post/",
+          );
+          const secondPostLink = Array.from(postLinks).find(
+            (link) => link.getAttribute("href") === "/blog/second-post/",
+          );
+
+          expect(firstPostLink.getAttribute("title")).to.equal("First Post");
+          expect(firstPostLink.textContent).to.equal("First Post");
 
-          expect(postLinks[1].getAttribute("href")).to.equal("/blog/second-post/");
-          expect(postLinks[1].getAttribute("title")).to.equal("Second Post");
-          expect(postLinks[1].textContent).to.equal("Second Post");
+          expect(secondPostLink.getAttribute("title")).to.equal("Second Post");
+          expect(secondPostLink.textContent).to.equal("Second Post");
         });
       });
     });
diff --git a/packages/cli/test/cases/build.default.static-asset-bundling/build.default.static-asset-bundling.spec.js b/packages/cli/test/cases/build.default.static-asset-bundling/build.default.static-asset-bundling.spec.js
index 4655a075f..78320dcf3 100644
--- a/packages/cli/test/cases/build.default.static-asset-bundling/build.default.static-asset-bundling.spec.js
+++ b/packages/cli/test/cases/build.default.static-asset-bundling/build.default.static-asset-bundling.spec.js
@@ -59,7 +59,7 @@ describe("Build Greenwood With: ", function () {
 
       before(async function () {
         const headerScripts = await Array.fromAsync(
-          fs.glob("header.*.js", { cwd: new URL("./public/", import.meta.url) }),
+          fs.glob("header.*.js", { cwd: new URL("./public/", import.meta.url).pathname }),
         );
 
         headerContents = await fs.readFile(
@@ -87,7 +87,7 @@ describe("Build Greenwood With: ", function () {
       before(async function () {
         assets = (
           await Array.fromAsync(
-            fs.glob("**", { cwd: new URL("./public/assets/", import.meta.url) }),
+            fs.glob("**", { cwd: new URL("./public/assets/", import.meta.url).pathname }),
           )
         ).filter((assets) => assets.indexOf(".") > 0);
       });
diff --git a/packages/cli/test/cases/build.default.workspace-nested-graph/build.default.workspace-nested-graph.spec.js b/packages/cli/test/cases/build.default.workspace-nested-graph/build.default.workspace-nested-graph.spec.js
new file mode 100644
index 000000000..4edfccef5
--- /dev/null
+++ b/packages/cli/test/cases/build.default.workspace-nested-graph/build.default.workspace-nested-graph.spec.js
@@ -0,0 +1,158 @@
+/*
+ * Use Case
+ * Run Greenwood with default config and nested directories in workspace with lots of nested pages.
+ *
+ * Result
+ * Test for correctly ordered graph.json and pages output, which by default should mimic
+ * the filesystem order by default.
+ *
+ * Command
+ * greenwood build
+ *
+ * User Config
+ * {
+ *   plugins: [greenwoodPluginMarkdown()]
+ * }
+ *
+ * User Workspace
+ * src/
+ *   pages/
+ *     blog/
+ *       2017/
+ *         03/26/index.html
+ *         03/30/index.html
+ *       2019/
+ *         11/11/index.html
+ *     index.html
+ *   index.html
+ *   404.html
+ */
+import chai from "chai";
+import fs from "node:fs";
+import path from "node:path";
+import { getOutputTeardownFiles } from "../../../../../test/utils.js";
+import { runSmokeTest } from "../../../../../test/smoke-test.js";
+import { Runner } from "gallinago";
+import { fileURLToPath } from "node:url";
+
+const expect = chai.expect;
+
+function generatePageHref(pagePath) {
+  return new URL(`./src/pages/${pagePath}`, import.meta.url).href;
+}
+
+describe("Build Greenwood With: ", function () {
+  const LABEL = "Default Greenwood Configuration and Workspace w/ Nested Directories";
+  const cliPath = path.join(process.cwd(), "packages/cli/src/bin.js");
+  const outputPath = fileURLToPath(new URL(".", import.meta.url));
+  let runner;
+
+  before(function () {
+    this.context = {
+      publicDir: path.join(outputPath, "public"),
+    };
+    runner = new Runner();
+  });
+
+  describe(LABEL, function () {
+    before(function () {
+      runner.setup(outputPath);
+      runner.runCommand(cliPath, "build");
+    });
+
+    runSmokeTest(["public", "index"], LABEL);
+
+    describe("Expected Graph Contents", function () {
+      let graph;
+
+      before(async function () {
+        graph = JSON.parse(
+          await fs.promises.readFile(path.join(this.context.publicDir, "graph.json"), "utf-8"),
+        );
+      });
+
+      // we _technically_ can't assume the order of pages but we can at least make sure all the files are there
+      // this could easily be solved by adding an `order` property to the page's frontmatter
+      // https://github.com/ProjectEvergreen/greenwood/pull/1308#issuecomment-3368603613
+      it("should have the expected ordering of pages in graph.json", function () {
+        expect(graph.length).to.equal(6);
+
+        const page404 = graph.find((page) => page.route === "/404/");
+        expect(page404.pageHref).to.equal(generatePageHref("404.html"));
+        expect(page404.id).to.be.equal("404");
+
+        const homePage = graph.find((page) => page.route === "/");
+        expect(homePage.pageHref).to.equal(generatePageHref("index.html"));
+        expect(homePage.id).to.be.equal("index");
+
+        const blogPage = graph.find((page) => page.route === "/blog/");
+        expect(blogPage.pageHref).to.equal(generatePageHref("blog/index.html"));
+        expect(blogPage.id).to.be.equal("blog-index");
+
+        const nestedPage = graph.find((page) => page.route === "/blog/2019/11/11/");
+        expect(nestedPage.pageHref).to.equal(generatePageHref("blog/2019/11/11/index.html"));
+        expect(nestedPage.id).to.be.equal("blog-2019-11-11-index");
+      });
+    });
+
+    describe("Blog Pages Directory", function () {
+      let graph;
+
+      before(async function () {
+        graph = JSON.parse(
+          await fs.promises.readFile(path.join(this.context.publicDir, "graph.json"), "utf-8"),
+        );
+      });
+
+      it("should create a top level blog pages directory", function () {
+        expect(fs.existsSync(path.join(this.context.publicDir, "./blog"))).to.be.true;
+      });
+
+      it("should create a directory for each year of blog pages", function () {
+        expect(fs.existsSync(path.join(this.context.publicDir, "blog/2017"))).to.be.true;
+        expect(fs.existsSync(path.join(this.context.publicDir, "blog/2019"))).to.be.true;
+      });
+
+      it("should have the expected pages for 2017 blog pages", function () {
+        graph
+          .filter((page) => {
+            return page.route.indexOf("2017") > 0;
+          })
+          .forEach((page) => {
+            const outputPath = path.join(this.context.publicDir, page.route, "index.html");
+            expect(fs.existsSync(outputPath)).to.be.true;
+          });
+      });
+
+      it("should have the expected pages for 2019 blog pages", function () {
+        graph
+          .filter((page) => {
+            return page.route.indexOf("2019") > 0;
+          })
+          .forEach((page) => {
+            const outputPath = path.join(this.context.publicDir, page.route, "index.html");
+            expect(fs.existsSync(outputPath)).to.be.true;
+          });
+      });
+
+      it("should have the expected content for each blog page", function () {
+        graph
+          .filter((page) => {
+            return page.route.indexOf(/\/blog\/[0-9]{4}/) > 0;
+          })
+          .forEach((page) => {
+            const contents = fs.readFileSync(
+              path.join(this.context.publicDir, page.route, "index.html"),
+              "utf-8",
+            );
+
+            expect(contents).to.contain(`<p>This is the post for page ${page.data.date}.</p>`);
+          });
+      });
+    });
+  });
+
+  after(function () {
+    runner.teardown(getOutputTeardownFiles(outputPath));
+  });
+});
diff --git a/packages/cli/test/cases/build.default.workspace-nested-graph/src/pages/404.html b/packages/cli/test/cases/build.default.workspace-nested-graph/src/pages/404.html
new file mode 100644
index 000000000..7cf14d2e5
--- /dev/null
+++ b/packages/cli/test/cases/build.default.workspace-nested-graph/src/pages/404.html
@@ -0,0 +1,16 @@
+<!doctype html>
+<html lang="en" prefix="og:http://ogp.me/ns#">
+  <head>
+    <title>Page Not Found</title>
+
+    <style>
+      h1 {
+        text-align: center;
+      }
+    </style>
+  </head>
+
+  <body>
+    <h1>Sorry, unfortunately the page could not be found.</h1>
+  </body>
+</html>
diff --git a/packages/cli/test/cases/build.default.workspace-nested-graph/src/pages/blog/2017/03/26/index.html b/packages/cli/test/cases/build.default.workspace-nested-graph/src/pages/blog/2017/03/26/index.html
new file mode 100644
index 000000000..37a2506d5
--- /dev/null
+++ b/packages/cli/test/cases/build.default.workspace-nested-graph/src/pages/blog/2017/03/26/index.html
@@ -0,0 +1,8 @@
+---
+title: "Lorum Ipsum"
+date: "03.26.2017"
+---
+
+<body>
+  <p>This is the post for page 03.26.2017.</p>
+</body>
diff --git a/packages/cli/test/cases/build.default.workspace-nested-graph/src/pages/blog/2017/03/30/index.html b/packages/cli/test/cases/build.default.workspace-nested-graph/src/pages/blog/2017/03/30/index.html
new file mode 100644
index 000000000..cd13e0fcc
--- /dev/null
+++ b/packages/cli/test/cases/build.default.workspace-nested-graph/src/pages/blog/2017/03/30/index.html
@@ -0,0 +1,8 @@
+---
+title: "Lorum Ipsum"
+date: "03.30.2017"
+---
+
+<body>
+  <p>This is the post for page 03.30.2017.</p>
+</body>
diff --git a/packages/cli/test/cases/build.default.workspace-nested-graph/src/pages/blog/2019/11/11/index.html b/packages/cli/test/cases/build.default.workspace-nested-graph/src/pages/blog/2019/11/11/index.html
new file mode 100644
index 000000000..39656933d
--- /dev/null
+++ b/packages/cli/test/cases/build.default.workspace-nested-graph/src/pages/blog/2019/11/11/index.html
@@ -0,0 +1,8 @@
+---
+title: "Lorum Ipsum"
+date: "11.11.2019"
+---
+
+<body>
+  <p>This is the post for page 11.11.2019.</p>
+</body>
diff --git a/packages/cli/test/cases/build.default.workspace-nested-graph/src/pages/blog/index.html b/packages/cli/test/cases/build.default.workspace-nested-graph/src/pages/blog/index.html
new file mode 100644
index 000000000..da1524850
--- /dev/null
+++ b/packages/cli/test/cases/build.default.workspace-nested-graph/src/pages/blog/index.html
@@ -0,0 +1,4 @@
+<body>
+  <h1>Blog Posts</h1>
+  <p>See our blog posts!</p>
+</body>
diff --git a/packages/cli/test/cases/build.default.workspace-nested-graph/src/pages/index.html b/packages/cli/test/cases/build.default.workspace-nested-graph/src/pages/index.html
new file mode 100644
index 000000000..471c741df
--- /dev/null
+++ b/packages/cli/test/cases/build.default.workspace-nested-graph/src/pages/index.html
@@ -0,0 +1,5 @@
+<html>
+  <body>
+    <p>This is the home page built by Greenwood. Make your own pages in src/pages/index.js!</p>
+  </body>
+</html>
diff --git a/packages/cli/test/cases/develop.default/develop.default.spec.js b/packages/cli/test/cases/develop.default/develop.default.spec.js
index 6487752d9..23a3bf323 100644
--- a/packages/cli/test/cases/develop.default/develop.default.spec.js
+++ b/packages/cli/test/cases/develop.default/develop.default.spec.js
@@ -531,7 +531,11 @@ describe("Develop Greenwood With: ", function () {
       let body;
 
       before(async function () {
-        response = await fetch(`${hostname}:${port}/node_modules/lit-html/lit-html.js.map`);
+        response = await fetch(`${hostname}:${port}/node_modules/lit-html/lit-html.js.map`, {
+          headers: {
+            "Content-Type": "application/json", // Essential for JSON bodies
+          },
+        });
         body = await response.clone().text();
       });
 
@@ -799,6 +803,9 @@ describe("Develop Greenwood With: ", function () {
         response = await fetch(`${hostname}:${port}/api/submit-json`, {
           method: "POST",
           body: JSON.stringify({ name: param }),
+          headers: {
+            "Content-Type": "application/json", // Essential for JSON bodies
+          },
         });
         data = await response.json();
       });
diff --git a/packages/cli/test/cases/serve.default.api/serve.default.api.spec.js b/packages/cli/test/cases/serve.default.api/serve.default.api.spec.js
index be48ac92f..3a8a5ac92 100644
--- a/packages/cli/test/cases/serve.default.api/serve.default.api.spec.js
+++ b/packages/cli/test/cases/serve.default.api/serve.default.api.spec.js
@@ -183,6 +183,9 @@ describe("Serve Greenwood With: ", function () {
       before(async function () {
         response = await fetch(`${hostname}/api/submit-json`, {
           method: "POST",
+          headers: {
+            "Content-Type": "application/json", // Essential for JSON bodies
+          },
           body: JSON.stringify({ name: param }),
         });
         data = await response.clone().json();
diff --git a/packages/cli/test/cases/serve.default.api/src/pages/api/submit-json.js b/packages/cli/test/cases/serve.default.api/src/pages/api/submit-json.js
index c73c35813..bd59cd62f 100644
--- a/packages/cli/test/cases/serve.default.api/src/pages/api/submit-json.js
+++ b/packages/cli/test/cases/serve.default.api/src/pages/api/submit-json.js
@@ -1,6 +1,6 @@
 export async function handler(request) {
-  const formData = await request.json();
-  const { name } = formData;
+  const data = await request.json();
+  const { name } = data;
   const body = { message: `Thank you ${name} for your submission!` };
 
   return new Response(JSON.stringify(body), {
diff --git a/packages/cli/test/cases/serve.default.error/serve.default.error.spec.js b/packages/cli/test/cases/serve.default.error/serve.default.error.spec.js
index 29939bc66..bb4977ee8 100644
--- a/packages/cli/test/cases/serve.default.error/serve.default.error.spec.js
+++ b/packages/cli/test/cases/serve.default.error/serve.default.error.spec.js
@@ -36,14 +36,10 @@ describe("Serve Greenwood With: ", function () {
 
   describe("Running the serve command without running the build command first", function () {
     it("should throw an error that no build output was detected", async function () {
-      try {
-        await runner.setup(outputPath);
-        await runner.runCommand(cliPath, "serve");
-      } catch (err) {
-        expect(err).to.contain(
-          "Error: No build output detected. Make sure you have run greenwood build",
-        );
-      }
+      await runner.setup(outputPath);
+      await expect(runner.runCommand(cliPath, "serve")).to.be.rejectedWith(
+        "No build output detected. Make sure you have run greenwood build",
+      );
     });
   });
 
diff --git a/packages/plugin-adapter-netlify/test/cases/build.default/build.default.spec.js b/packages/plugin-adapter-netlify/test/cases/build.default/build.default.spec.js
index e0c702d86..2475ff6f6 100644
--- a/packages/plugin-adapter-netlify/test/cases/build.default/build.default.spec.js
+++ b/packages/plugin-adapter-netlify/test/cases/build.default/build.default.spec.js
@@ -681,21 +681,33 @@ describe("Build Greenwood With: ", function () {
         );
       });
 
+      // we _technically_ can't assume the order of pages but we can at least make sure all the files are there
+      // this could easily be solved by adding an `order` property to the page's frontmatter
+      // https://github.com/ProjectEvergreen/greenwood/pull/1308#issuecomment-3368603613
       it("should return the expected response when the serverless adapter entry point handler is invoked", async function () {
-        expect(redirectsFileContents).to.be.equal(
-          `/artists/ /.netlify/functions/artists 200
-/blog/first-post/ /.netlify/functions/blog-first-post 200
-/blog/ /.netlify/functions/blog-index 200
-/ /.netlify/functions/index 200
-/post/ /.netlify/functions/post 200
-/users/ /.netlify/functions/users 200
-/api/fragment /.netlify/functions/api-fragment 200
-/api/greeting /.netlify/functions/api-greeting 200
-/api/nested/endpoint /.netlify/functions/api-nested-endpoint 200
-/api/search /.netlify/functions/api-search 200
-/api/submit-form-data /.netlify/functions/api-submit-form-data 200
-/api/submit-json /.netlify/functions/api-submit-json 200
-`,
+        expect(redirectsFileContents).to.contain("/artists/ /.netlify/functions/artists 200");
+        expect(redirectsFileContents).to.contain(
+          "/blog/first-post/ /.netlify/functions/blog-first-post 200",
+        );
+        expect(redirectsFileContents).to.contain("/blog/ /.netlify/functions/blog-index 200");
+        expect(redirectsFileContents).to.contain("/ /.netlify/functions/index 200");
+        expect(redirectsFileContents).to.contain("/post/ /.netlify/functions/post 200");
+        expect(redirectsFileContents).to.contain("/users/ /.netlify/functions/users 200");
+        expect(redirectsFileContents).to.contain(
+          "/api/fragment /.netlify/functions/api-fragment 200",
+        );
+        expect(redirectsFileContents).to.contain(
+          "/api/greeting /.netlify/functions/api-greeting 200",
+        );
+        expect(redirectsFileContents).to.contain(
+          "/api/nested/endpoint /.netlify/functions/api-nested-endpoint 200",
+        );
+        expect(redirectsFileContents).to.contain("/api/search /.netlify/functions/api-search 200");
+        expect(redirectsFileContents).to.contain(
+          "/api/submit-form-data /.netlify/functions/api-submit-form-data 200",
+        );
+        expect(redirectsFileContents).to.contain(
+          "/api/submit-json /.netlify/functions/api-submit-json 200",
         );
       });
     });
diff --git a/packages/plugin-css-modules/test/cases/develop.default/develop.default.spec.js b/packages/plugin-css-modules/test/cases/develop.default/develop.default.spec.js
index a4107a67e..b025e4e93 100644
--- a/packages/plugin-css-modules/test/cases/develop.default/develop.default.spec.js
+++ b/packages/plugin-css-modules/test/cases/develop.default/develop.default.spec.js
@@ -219,7 +219,7 @@ describe("Develop Greenwood With: ", function () {
             headerModuleText = await response.text();
             modulesMaps = await Array.fromAsync(
               fs.promises.glob("*.map.json", {
-                cwd: new URL("./.greenwood/__css-modules-map/", import.meta.url),
+                cwd: new URL("./.greenwood/__css-modules-map/", import.meta.url).pathname,
               }),
             );
           });
diff --git a/packages/plugin-graphql/test/cases/query-graph/query-graph.spec.js b/packages/plugin-graphql/test/cases/query-graph/query-graph.spec.js
index e39e1fdfb..b72518609 100644
--- a/packages/plugin-graphql/test/cases/query-graph/query-graph.spec.js
+++ b/packages/plugin-graphql/test/cases/query-graph/query-graph.spec.js
@@ -97,14 +97,16 @@ describe("Build Greenwood With: ", function () {
         expect(lists.length).to.be.equal(1);
       });
 
+      // we _technically_ can't assume the order of pages but we can at least make sure all the files are there
+      // this could easily be solved by adding an `order` property to the page's frontmatter
+      // https://github.com/ProjectEvergreen/greenwood/pull/1308#issuecomment-3368603613
       it("should have a expected navigation output in the <header> based on pages in the graph", function () {
         const listItems = dom.window.document.querySelectorAll("body ul li");
 
         expect(listItems.length).to.be.equal(3);
-
-        expect(listItems[0].innerHTML).to.contain("First Post");
-        expect(listItems[1].innerHTML).to.contain("Second Post");
-        expect(listItems[2].innerHTML).to.contain("Home");
+        listItems.forEach((item) => {
+          expect(["First Post", "Second Post", "Home"].includes(item.innerHTML));
+        });
       });
     });
   });
diff --git a/packages/plugin-markdown/test/cases/build.default.workspace-nested/build.default.workspace-nested.spec.js b/packages/plugin-markdown/test/cases/build.default.workspace-nested/build.default.workspace-nested.spec.js
index 7f0ecc8be..5eec2acb2 100644
--- a/packages/plugin-markdown/test/cases/build.default.workspace-nested/build.default.workspace-nested.spec.js
+++ b/packages/plugin-markdown/test/cases/build.default.workspace-nested/build.default.workspace-nested.spec.js
@@ -54,10 +54,6 @@ import { fileURLToPath } from "node:url";
 
 const expect = chai.expect;
 
-function generatePageHref(pagePath) {
-  return new URL(`./src/pages/${pagePath}`, import.meta.url).href;
-}
-
 describe("Build Greenwood With Markdown Plugin: ", function () {
   const LABEL = "Default Greenwood Configuration and Default Workspace w/ Nested Directories";
   const cliPath = path.join(process.cwd(), "packages/cli/src/bin.js");
@@ -88,36 +84,6 @@ describe("Build Greenwood With Markdown Plugin: ", function () {
         );
       });
 
-      it("should have the expected ordering of pages in graph.json", function () {
-        expect(graph.length).to.equal(21);
-
-        expect(graph[0].pageHref).to.equal(generatePageHref("404.html"));
-        expect(graph[0].id).to.be.equal("404");
-        expect(graph[1].pageHref).to.equal(generatePageHref("blog/2017/03/26/index.md"));
-        expect(graph[1].id).to.be.equal("blog-2017-03-26-index");
-        expect(graph[2].pageHref).to.equal(generatePageHref("blog/2017/03/30/index.md"));
-        expect(graph[3].pageHref).to.equal(generatePageHref("blog/2017/04/10/index.md"));
-        expect(graph[4].pageHref).to.equal(generatePageHref("blog/2017/04/22/index.md"));
-        expect(graph[5].pageHref).to.equal(generatePageHref("blog/2017/05/05/index.md"));
-        expect(graph[6].pageHref).to.equal(generatePageHref("blog/2017/06/07/index.md"));
-        expect(graph[7].pageHref).to.equal(generatePageHref("blog/2017/09/10/index.md"));
-        expect(graph[8].pageHref).to.equal(generatePageHref("blog/2017/10/15/index.md"));
-        expect(graph[9].pageHref).to.equal(generatePageHref("blog/2018/01/24/index.md"));
-        expect(graph[10].pageHref).to.equal(generatePageHref("blog/2018/05/16/index.md"));
-        expect(graph[11].pageHref).to.equal(generatePageHref("blog/2018/06/06/index.md"));
-        expect(graph[12].pageHref).to.equal(generatePageHref("blog/2018/09/26/index.md"));
-        expect(graph[13].pageHref).to.equal(generatePageHref("blog/2018/10/28/index.md"));
-        expect(graph[14].pageHref).to.equal(generatePageHref("blog/2018/11/19/index.md"));
-        expect(graph[15].pageHref).to.equal(generatePageHref("blog/2019/11/11/index.md"));
-        expect(graph[16].pageHref).to.equal(generatePageHref("blog/2020/04/07/index.md"));
-        expect(graph[17].pageHref).to.equal(generatePageHref("blog/2020/08/15/index.md"));
-        expect(graph[18].pageHref).to.equal(generatePageHref("blog/2020/10/28/index.md"));
-        expect(graph[19].pageHref).to.equal(generatePageHref("blog/index.md"));
-        expect(graph[19].id).to.be.equal("blog-index");
-        expect(graph[20].pageHref).to.equal(generatePageHref("index.html"));
-        expect(graph[20].id).to.be.equal("index");
-      });
-
       it("should create a top level blog pages directory", function () {
         expect(fs.existsSync(path.join(this.context.publicDir, "./blog"))).to.be.true;
       });