diff --git a/docs-app/public/docs/meta.jsonc b/docs-app/public/docs/meta.jsonc
index 88a15d88..187770af 100644
--- a/docs-app/public/docs/meta.jsonc
+++ b/docs-app/public/docs/meta.jsonc
@@ -1,5 +1,5 @@
 {
   // We want usage to be first, which breaks the
   // default sort order provided by the filesystem: Alphabetical
-  "order": ["usage", "components", "plugins"],
+  "order": ["usage", "plugins"],
 }
diff --git a/docs-app/public/docs/usage/meta.jsonc b/docs-app/public/docs/usage/meta.jsonc
index 711bf244..9062af7b 100644
--- a/docs-app/public/docs/usage/meta.jsonc
+++ b/docs-app/public/docs/usage/meta.jsonc
@@ -1,4 +1,4 @@
 {
   // This is in order of need-to-know
-  "order": ["setup", "rendering-pages", "ordering-pages"],
+  "order": ["setup", "rendering-pages", "ordering-pages", "testing"],
 }
diff --git a/fixtures/discover/c/index.md b/fixtures/discover/c/index.md
new file mode 100644
index 00000000..e69de29b
diff --git a/fixtures/discover/c/meta.jsonc b/fixtures/discover/c/meta.jsonc
index beb3dc1f..3092b354 100644
--- a/fixtures/discover/c/meta.jsonc
+++ b/fixtures/discover/c/meta.jsonc
@@ -1,3 +1,3 @@
 {
-  "order": ["c-b", "c-a"],
+  "order": ["c-b", "c-a", "d", "e"],
 }
diff --git a/fixtures/discover/meta.jsonc b/fixtures/discover/meta.jsonc
index 798e090f..dba55c98 100644
--- a/fixtures/discover/meta.jsonc
+++ b/fixtures/discover/meta.jsonc
@@ -1,3 +1,3 @@
 {
-  "order": ["b", "a"],
+  "order": ["c"],
 }
diff --git a/package.json b/package.json
index 5418c418..fa8a5592 100644
--- a/package.json
+++ b/package.json
@@ -84,7 +84,8 @@
     "build:declarations": "tsc --declaration",
     "_syncPnpm": "pnpm sync-dependencies-meta-injected",
     "start:typedoc": "typedoc --options ./typedoc.config.json --watch",
-    "test:node": "vitest --run"
+    "test:node": "vitest --run",
+    "test:dev": "vitest dev"
   },
   "peerDependencies": {
     "@ember/test-waiters": "^3.1.0",
diff --git a/src/plugins/markdown-pages/discover.test.ts b/src/plugins/markdown-pages/discover.test.ts
index 7708e4a7..1a3b264d 100644
--- a/src/plugins/markdown-pages/discover.test.ts
+++ b/src/plugins/markdown-pages/discover.test.ts
@@ -15,13 +15,19 @@ describe('discover', () => {
 
     expect(result.groups[0]?.tree).toMatchInlineSnapshot(`
       {
-        "first": "/c/c-b.md",
+        "first": "/c/index.md",
         "name": "root",
         "pages": [
           {
-            "first": "/c/c-b.md",
+            "first": "/c/index.md",
             "name": "c",
             "pages": [
+              {
+                "cleanedName": "index",
+                "groupName": "c",
+                "name": "index",
+                "path": "/c/index.md",
+              },
               {
                 "cleanedName": "c b",
                 "groupName": "c",
diff --git a/src/plugins/markdown-pages/sort.applyPredestinedOrder.test.ts b/src/plugins/markdown-pages/sort.applyPredestinedOrder.test.ts
index 380e0e10..60cfe344 100644
--- a/src/plugins/markdown-pages/sort.applyPredestinedOrder.test.ts
+++ b/src/plugins/markdown-pages/sort.applyPredestinedOrder.test.ts
@@ -4,14 +4,14 @@ import { applyPredestinedOrder } from './sort.js';
 
 describe('applyPredestinedOrder', () => {
   test('it works', () => {
-    expect(applyPredestinedOrder(['c', 'b', 'a'], ['a', 'c'])).deep.equal(['a', 'c', 'b']);
+    expect(applyPredestinedOrder(['c', 'b', 'a'], ['a', 'c', 'b'])).deep.equal(['a', 'c', 'b']);
   });
 
   test('it works with objects', () => {
     expect(
       applyPredestinedOrder(
         [{ name: 'c' }, { name: 'b' }, { name: 'a' }],
-        ['a', 'c'],
+        ['a', 'c', 'b'],
         (item) => item.name
       )
     ).deep.equal([{ name: 'a' }, { name: 'c' }, { name: 'b' }]);
@@ -21,19 +21,34 @@ describe('applyPredestinedOrder', () => {
     expect(applyPredestinedOrder(['c', 'a'], ['a', 'c'])).deep.equal(['a', 'c']);
   });
 
-  test('it works when the order specifies things that do not exist', () => {
-    expect(applyPredestinedOrder(['c', 'b', 'a'], ['a', 'c', 'x', 'y', 'z'])).deep.equal([
-      'a',
-      'c',
-      'b',
-    ]);
+  test('it handles index pages as always first', () => {
+    expect(applyPredestinedOrder(['c', 'a', 'index'], ['a', 'c'])).deep.equal(['index', 'a', 'c']);
   });
 
-  test('it works when the order specifies duplicates', () => {
-    expect(applyPredestinedOrder(['c', 'b', 'a'], ['a', 'c', 'a', 'c'])).deep.equal([
-      'a',
-      'c',
-      'b',
-    ]);
+  test('it errors when the order specifies things that do not exist', () => {
+    expect(() => applyPredestinedOrder(['c', 'b', 'a'], ['a', 'c', 'x'])).toThrow(
+      'Order configuration specified "x" but it was not found in the list. Pages are ["c","b","a"]'
+    );
+  });
+
+  test('it errors when order is a different length than list', () => {
+    expect(() => applyPredestinedOrder(['c', 'b', 'a', 'd'], ['a', 'c', 'b']))
+      .toThrow(`Order configuration specified different number of arguments than available pages:
+Order: ["a","c","b"]
+Actual: ["c","b","a","d"]`);
+  });
+
+  test('it errors if duplicate pages are specified', () => {
+    expect(() => applyPredestinedOrder(['c', 'b', 'a'], ['a', 'c', 'a', 'c']))
+      .toThrow(`Order configuration specified duplicate pages:
+Unique: ["a","c"]
+Order: ["a","c","a","c"]
+Actual: ["c","b","a"]`);
+  });
+
+  test('it errors if a configuration order option is empty', () => {
+    expect(() => applyPredestinedOrder(['c', 'b', 'a'], ['a', '', 'd'])).toThrow(
+      `Order configuration found an empty string at index 1`
+    );
   });
 });
diff --git a/src/plugins/markdown-pages/sort.js b/src/plugins/markdown-pages/sort.js
index 40b67d10..ce7d72bf 100644
--- a/src/plugins/markdown-pages/sort.js
+++ b/src/plugins/markdown-pages/sort.js
@@ -1,3 +1,19 @@
+/**
+ * @param {unknown[]} arr
+ * @returns {unknown[]}
+ */
+function uniq(arr) {
+  return Array.from(new Set(arr));
+}
+
+/**
+ * @param {string} path
+ * @returns {string}
+ */
+function findPathForJsonc(path) {
+  return path.replace(/\/meta\.jsonc?$/, '');
+}
+
 /**
  * Tutorials (and groups) are all 123-name
  * This is so that we can sort them manually on the file system.
@@ -49,21 +65,39 @@ export function betterSort(property) {
  * @param {Item[]} list
  * @param {string[]} order
  * @param {(item: Item) => any} [ find ]
+ * @throws {Error}
  * @returns {Item[]}
  */
 export function applyPredestinedOrder(list, order, find = (x) => x) {
-  let result = [];
+  let indexPage = list.find((x) => find(x) === 'index');
+  let result = indexPage ? [indexPage] : [];
+
+  list = list.filter((a) => a !== indexPage);
+
+  let remaining = [...list];
 
-  let remaining = list;
+  if (uniq(order).length !== order.length)
+    throw new Error(`Order configuration specified duplicate pages:
+Unique: ${JSON.stringify(uniq(order))}
+Order: ${JSON.stringify(order)}
+Actual: ${JSON.stringify(list.map(find))}`);
 
-  for (let i = 0; i < Math.max(list.length, order.length); i++) {
+  if (order.length !== list.length)
+    throw new Error(`Order configuration specified different number of arguments than available pages:
+Order: ${JSON.stringify(order)}
+Actual: ${JSON.stringify(list.map(find))}`);
+
+  for (let i = 0; i < order.length; i++) {
     let current = order[i];
 
-    if (!current) break;
+    if (!current) throw new Error(`Order configuration found an empty string at index ${i}`);
 
     let foundIndex = remaining.findIndex((x) => find(x) === current);
 
-    if (foundIndex < 0) continue;
+    if (foundIndex < 0)
+      throw new Error(
+        `Order configuration specified "${current}" but it was not found in the list. Pages are ${JSON.stringify(list.map(find))}`
+      );
 
     // remove
     let [found] = remaining.splice(foundIndex, 1);
@@ -73,7 +107,11 @@ export function applyPredestinedOrder(list, order, find = (x) => x) {
     result.push(found);
   }
 
-  result.push(...remaining);
+  if (remaining.length > 0) {
+    throw new Error(
+      `Order configuration did not specify all pages. Remaining pages are ${JSON.stringify(remaining.map(find))}`
+    );
+  }
 
   return result;
 }
@@ -93,16 +131,22 @@ export function sortTree(tree, configs, parents = []) {
 
   if (configs.length > 0) {
     let subPath = `${[...parents, tree.name].join('/')}`;
-    let config = configs.filter(Boolean).find((config) => config.path.startsWith(subPath))?.config;
+    let config = configs
+      .filter(Boolean)
+      .find((config) => findPathForJsonc(config.path) === subPath)?.config;
 
     if (!config?.order) {
       return tree;
     }
 
     // Should the name always avoid the extension?
-    let replacementPages = applyPredestinedOrder(tree.pages, config.order, (page) => page.name);
+    try {
+      let replacementPages = applyPredestinedOrder(tree.pages, config.order, (page) => page.name);
 
-    tree.pages = replacementPages;
+      tree.pages = replacementPages;
+    } catch (error) {
+      throw new Error(`Error while sorting tree at ${subPath}.\n${error}`);
+    }
   }
 
   return tree;
diff --git a/src/plugins/markdown-pages/sort.sortTree.test.ts b/src/plugins/markdown-pages/sort.sortTree.test.ts
index 38c10e32..e9314fdb 100644
--- a/src/plugins/markdown-pages/sort.sortTree.test.ts
+++ b/src/plugins/markdown-pages/sort.sortTree.test.ts
@@ -70,20 +70,20 @@ describe('sortTree', () => {
         name: 'top',
         pages: [
           {
-            name: 'second',
+            name: 'child',
             pages: [
               {
-                path: '/top/second/second',
+                path: '/top/child/second',
                 name: 'second',
                 groupName: 'top',
                 cleanedName: 'second',
               },
-              { name: 'first', path: '/top/second/first', groupName: 'top', cleanedName: 'first' },
+              { name: 'first', path: '/top/child/first', groupName: 'top', cleanedName: 'first' },
             ],
           },
         ],
       },
-      [{ path: 'top/second/meta.jsonc', config: { order: ['first', 'second'] } }]
+      [{ path: 'top/child/meta.jsonc', config: { order: ['first', 'second'] } }]
     );
 
     expect(result.pages.length).toEqual(1);