diff --git a/src/Extension/Extension.php b/src/Extension/Extension.php
index 0844164c49a..de5e5f30dde 100644
--- a/src/Extension/Extension.php
+++ b/src/Extension/Extension.php
@@ -64,7 +64,7 @@ protected static function nameToId($name)
      * Unique Id of the extension.
      *
      * @info    Identical to the directory in the extensions directory.
-     * @example flarum_suspend
+     * @example flarum-suspend
      *
      * @var string
      */
@@ -91,6 +91,14 @@ protected static function nameToId($name)
      */
     protected $extensionDependencyIds;
 
+    /**
+     * The IDs of all Flarum extensions that this extension should be booted after
+     * if enabled.
+     *
+     * @var string[]
+     */
+    protected $optionalDependencyIds;
+
     /**
      * Whether the extension is installed.
      *
@@ -203,16 +211,29 @@ public function setVersion($version)
      * @param array $extensionSet: An associative array where keys are the composer package names
      *                             of installed extensions. Used to figure out which dependencies
      *                             are flarum extensions.
+     * @param array $enabledIds:   An associative array where keys are the composer package names
+     *                             of enabled extensions. Used to figure out optional dependencies.
      */
-    public function calculateDependencies($extensionSet)
+    public function calculateDependencies($extensionSet, $enabledIds)
     {
         $this->extensionDependencyIds = (new Collection(Arr::get($this->composerJson, 'require', [])))
             ->keys()
             ->filter(function ($key) use ($extensionSet) {
                 return array_key_exists($key, $extensionSet);
-            })->map(function ($key) {
+            })
+            ->map(function ($key) {
+                return static::nameToId($key);
+            })
+            ->toArray();
+
+        $this->optionalDependencyIds = (new Collection(Arr::get($this->composerJson, 'extra.flarum-extension.optional-dependencies', [])))
+            ->map(function ($key) {
                 return static::nameToId($key);
-            })->toArray();
+            })
+            ->filter(function ($key) use ($enabledIds) {
+                return array_key_exists($key, $enabledIds);
+            })
+            ->toArray();
     }
 
     /**
@@ -299,11 +320,22 @@ public function getPath()
      *
      * @return array
      */
-    public function getExtensionDependencyIds()
+    public function getExtensionDependencyIds(): array
     {
         return $this->extensionDependencyIds;
     }
 
+    /**
+     * The IDs of all Flarum extensions that this extension should be booted after
+     * if enabled.
+     *
+     * @return array
+     */
+    public function getOptionalDependencyIds(): array
+    {
+        return $this->optionalDependencyIds;
+    }
+
     private function getExtenders(): array
     {
         $extenderFile = $this->getExtenderFile();
@@ -455,6 +487,7 @@ public function toArray()
             'hasAssets'              => $this->hasAssets(),
             'hasMigrations'          => $this->hasMigrations(),
             'extensionDependencyIds' => $this->getExtensionDependencyIds(),
+            'optionalDependencyIds'  => $this->getOptionalDependencyIds(),
             'links'                  => $this->getLinks(),
         ], $this->composerJson);
     }
diff --git a/src/Extension/ExtensionManager.php b/src/Extension/ExtensionManager.php
index 6f5ee9ba859..58a77e7f0af 100644
--- a/src/Extension/ExtensionManager.php
+++ b/src/Extension/ExtensionManager.php
@@ -86,7 +86,9 @@ public function getExtensions()
             // We calculate and store a set of composer package names for all installed Flarum extensions,
             // so we know what is and isn't a flarum extension in `calculateDependencies`.
             // Using keys of an associative array allows us to do these checks in constant time.
+            // We do the same for enabled extensions, for optional dependencies.
             $installedSet = [];
+            $enabledIds = array_flip($this->getEnabled());
 
             foreach ($installed as $package) {
                 if (Arr::get($package, 'type') != 'flarum-extension' || empty(Arr::get($package, 'name'))) {
@@ -110,7 +112,7 @@ public function getExtensions()
             }
 
             foreach ($extensions as $extension) {
-                $extension->calculateDependencies($installedSet);
+                $extension->calculateDependencies($installedSet, $enabledIds);
             }
 
             $this->extensions = $extensions->sortBy(function ($extension, $name) {
@@ -348,13 +350,21 @@ public function getEnabled()
     /**
      * Persist the currently enabled extensions.
      *
-     * @param array $enabled
+     * @param array $enabledIds
      */
-    protected function setEnabled(array $enabled)
+    protected function setEnabled(array $enabledIds)
     {
-        $enabled = array_values(array_unique($enabled));
+        $enabled = array_map(function ($id) {
+            return $this->getExtension($id);
+        }, array_unique($enabledIds));
 
-        $this->config->set('extensions_enabled', json_encode($enabled));
+        $sortedEnabled = static::resolveExtensionOrder($enabled)['valid'];
+
+        $sortedEnabledIds = array_map(function (Extension $extension) {
+            return $extension->getId();
+        }, $sortedEnabled);
+
+        $this->config->set('extensions_enabled', json_encode($sortedEnabledIds));
     }
 
     /**
@@ -382,4 +392,92 @@ public static function pluckTitles(array $exts)
             return $extension->getTitle();
         }, $exts);
     }
+
+    /**
+     * Sort a list of extensions so that they are properly resolved in respect to order.
+     * Effectively just topological sorting.
+     *
+     * @param Extension[] $extensionList: an array of \Flarum\Extension\Extension objects
+     *
+     * @return array with 2 keys: 'valid' points to an ordered array of \Flarum\Extension\Extension
+     *                            'missingDependencies' points to an associative array of extensions that could not be resolved due
+     *                                to missing dependencies, in the format extension id => array of missing dependency IDs.
+     *                            'circularDependencies' points to an array of extensions ids of extensions
+     *                                that cannot be processed due to circular dependencies
+     */
+    public static function resolveExtensionOrder($extensionList)
+    {
+        $extensionIdMapping = []; // Used for caching so we don't rerun ->getExtensions every time.
+
+        // This is an implementation of Kahn's Algorithm (https://dl.acm.org/doi/10.1145/368996.369025)
+        $extensionGraph = [];
+        $output = [];
+        $missingDependencies = []; // Extensions are invalid if they are missing dependencies, or have circular dependencies.
+        $circularDependencies = [];
+        $pendingQueue = [];
+        $inDegreeCount = []; // How many extensions are dependent on a given extension?
+
+        foreach ($extensionList as $extension) {
+            $extensionIdMapping[$extension->getId()] = $extension;
+        }
+
+        foreach ($extensionList as $extension) {
+            $optionalDependencies = array_filter($extension->getOptionalDependencyIds(), function ($id) use ($extensionIdMapping) {
+                return array_key_exists($id, $extensionIdMapping);
+            });
+            $extensionGraph[$extension->getId()] = array_merge($extension->getExtensionDependencyIds(), $optionalDependencies);
+
+            foreach ($extensionGraph[$extension->getId()] as $dependency) {
+                $inDegreeCount[$dependency] = array_key_exists($dependency, $inDegreeCount) ? $inDegreeCount[$dependency] + 1 : 1;
+            }
+        }
+
+        foreach ($extensionList as $extension) {
+            if (! array_key_exists($extension->getId(), $inDegreeCount)) {
+                $inDegreeCount[$extension->getId()] = 0;
+                $pendingQueue[] = $extension->getId();
+            }
+        }
+
+        while (! empty($pendingQueue)) {
+            $activeNode = array_shift($pendingQueue);
+            $output[] = $activeNode;
+
+            foreach ($extensionGraph[$activeNode] as $dependency) {
+                $inDegreeCount[$dependency] -= 1;
+
+                if ($inDegreeCount[$dependency] === 0) {
+                    if (! array_key_exists($dependency, $extensionGraph)) {
+                        // Missing Dependency
+                        $missingDependencies[$activeNode] = array_merge(
+                            Arr::get($missingDependencies, $activeNode, []),
+                            [$dependency]
+                        );
+                    } else {
+                        $pendingQueue[] = $dependency;
+                    }
+                }
+            }
+        }
+
+        $validOutput = array_filter($output, function ($extension) use ($missingDependencies) {
+            return ! array_key_exists($extension, $missingDependencies);
+        });
+
+        $validExtensions = array_reverse(array_map(function ($extensionId) use ($extensionIdMapping) {
+            return $extensionIdMapping[$extensionId];
+        }, $validOutput)); // Reversed as required by Kahn's algorithm.
+
+        foreach ($inDegreeCount as $id => $count) {
+            if ($count != 0) {
+                $circularDependencies[] = $id;
+            }
+        }
+
+        return [
+            'valid' => $validExtensions,
+            'missingDependencies' => $missingDependencies,
+            'circularDependencies' => $circularDependencies
+        ];
+    }
 }
diff --git a/tests/unit/Foundation/ExtensionDependencyResolutionTest.php b/tests/unit/Foundation/ExtensionDependencyResolutionTest.php
new file mode 100644
index 00000000000..39fc66ab7d9
--- /dev/null
+++ b/tests/unit/Foundation/ExtensionDependencyResolutionTest.php
@@ -0,0 +1,142 @@
+<?php
+
+/*
+ * This file is part of Flarum.
+ *
+ * For detailed copyright and license information, please view the
+ * LICENSE file that was distributed with this source code.
+ */
+
+namespace Flarum\Tests\unit\Foundation;
+
+use Flarum\Extension\ExtensionManager;
+use Flarum\Tests\unit\TestCase;
+
+class ExtensionDependencyResolutionTest extends TestCase
+{
+    public function setUp(): void
+    {
+        parent::setUp();
+
+        $this->tags = new FakeExtension('flarum-tags', []);
+        $this->categories = new FakeExtension('flarum-categories', ['flarum-tags', 'flarum-tag-backgrounds']);
+        $this->tagBackgrounds = new FakeExtension('flarum-tag-backgrounds', ['flarum-tags']);
+        $this->something = new FakeExtension('flarum-something', ['flarum-categories', 'flarum-help']);
+        $this->help = new FakeExtension('flarum-help', []);
+        $this->missing = new FakeExtension('flarum-missing', ['this-does-not-exist', 'flarum-tags', 'also-not-exists']);
+        $this->circular1 = new FakeExtension('circular1', ['circular2']);
+        $this->circular2 = new FakeExtension('circular2', ['circular1']);
+        $this->optionalDependencyCategories = new FakeExtension('flarum-categories', ['flarum-tags'], ['flarum-tag-backgrounds']);
+    }
+
+    /** @test */
+    public function works_with_empty_set()
+    {
+        $expected = [
+            'valid' => [],
+            'missingDependencies' => [],
+            'circularDependencies' => [],
+        ];
+
+        $this->assertEquals($expected, ExtensionManager::resolveExtensionOrder([]));
+    }
+
+    /** @test */
+    public function works_with_proper_data()
+    {
+        $exts = [$this->tags, $this->categories, $this->tagBackgrounds, $this->something, $this->help];
+
+        $expected = [
+            'valid' => [$this->tags, $this->tagBackgrounds, $this->help, $this->categories, $this->something],
+            'missingDependencies' => [],
+            'circularDependencies' => [],
+        ];
+
+        $this->assertEquals($expected, ExtensionManager::resolveExtensionOrder($exts));
+    }
+
+    /** @test */
+    public function works_with_missing_dependencies()
+    {
+        $exts = [$this->tags, $this->categories, $this->tagBackgrounds, $this->something, $this->help, $this->missing];
+
+        $expected = [
+            'valid' => [$this->tags, $this->tagBackgrounds, $this->help, $this->categories, $this->something],
+            'missingDependencies' => ['flarum-missing' => ['this-does-not-exist', 'also-not-exists']],
+            'circularDependencies' => [],
+        ];
+
+        $this->assertEquals($expected, ExtensionManager::resolveExtensionOrder($exts));
+    }
+
+    /** @test */
+    public function works_with_circular_dependencies()
+    {
+        $exts = [$this->tags, $this->categories, $this->tagBackgrounds, $this->something, $this->help, $this->circular1, $this->circular2];
+
+        $expected = [
+            'valid' => [$this->tags, $this->tagBackgrounds, $this->help, $this->categories, $this->something],
+            'missingDependencies' => [],
+            'circularDependencies' => ['circular2', 'circular1'],
+        ];
+
+        $this->assertEquals($expected, ExtensionManager::resolveExtensionOrder($exts));
+    }
+
+    /** @test */
+    public function works_with_optional_dependencies()
+    {
+        $exts = [$this->tags, $this->optionalDependencyCategories, $this->tagBackgrounds, $this->something, $this->help];
+
+        $expected = [
+            'valid' => [$this->tags, $this->tagBackgrounds, $this->help, $this->optionalDependencyCategories, $this->something],
+            'missingDependencies' => [],
+            'circularDependencies' => [],
+        ];
+
+        $this->assertEquals($expected, ExtensionManager::resolveExtensionOrder($exts));
+    }
+
+    /** @test */
+    public function works_with_optional_dependencies_if_optional_dependency_missing()
+    {
+        $exts = [$this->tags, $this->optionalDependencyCategories, $this->something, $this->help];
+
+        $expected = [
+            'valid' => [$this->tags, $this->help, $this->optionalDependencyCategories, $this->something],
+            'missingDependencies' => [],
+            'circularDependencies' => [],
+        ];
+
+        $this->assertEquals($expected, ExtensionManager::resolveExtensionOrder($exts));
+    }
+}
+
+class FakeExtension
+{
+    protected $id;
+    protected $extensionDependencies;
+    protected $optionalDependencies;
+
+    public function __construct($id, $extensionDependencies, $optionalDependencies = [])
+    {
+        $this->id = $id;
+        $this->extensionDependencies = $extensionDependencies;
+        $this->optionalDependencies = $optionalDependencies;
+    }
+
+    public function getId()
+    {
+        return $this->id;
+    }
+
+    public function getExtensionDependencyIds()
+    {
+        return $this->extensionDependencies;
+    }
+
+    public function getOptionalDependencyIds()
+    {
+        return $this->optionalDependencies;
+    }
+}