diff --git a/app/Console/Commands/UpdateUrl.php b/app/Console/Commands/UpdateUrl.php
index 0c27f819c..2a1688468 100644
--- a/app/Console/Commands/UpdateUrl.php
+++ b/app/Console/Commands/UpdateUrl.php
@@ -4,6 +4,7 @@ namespace BookStack\Console\Commands;
 
 use Illuminate\Console\Command;
 use Illuminate\Database\Connection;
+use Illuminate\Support\Facades\DB;
 
 class UpdateUrl extends Command
 {
@@ -66,17 +67,44 @@ class UpdateUrl extends Command
 
         foreach ($columnsToUpdateByTable as $table => $columns) {
             foreach ($columns as $column) {
-                $changeCount = $this->db->table($table)->update([
-                    $column => $this->db->raw("REPLACE({$column}, '{$oldUrl}', '{$newUrl}')")
-                ]);
+                $changeCount = $this->replaceValueInTable($table, $column, $oldUrl, $newUrl);
                 $this->info("Updated {$changeCount} rows in {$table}->{$column}");
             }
         }
 
+        $jsonColumnsToUpdateByTable = [
+            "settings" => ["value"],
+        ];
+
+        foreach ($jsonColumnsToUpdateByTable as $table => $columns) {
+            foreach ($columns as $column) {
+                $oldJson = trim(json_encode($oldUrl), '"');
+                $newJson = trim(json_encode($newUrl), '"');
+                $changeCount = $this->replaceValueInTable($table, $column, $oldJson, $newJson);
+                $this->info("Updated {$changeCount} JSON encoded rows in {$table}->{$column}");
+            }
+        }
+
         $this->info("URL update procedure complete.");
+        $this->info('============================================================================');
+        $this->info('Be sure to run "php artisan cache:clear" to clear any old URLs in the cache.');
+        $this->info('============================================================================');
         return 0;
     }
 
+    /**
+     * Perform a find+replace operations in the provided table and column.
+     * Returns the count of rows changed.
+     */
+    protected function replaceValueInTable(string $table, string $column, string $oldUrl, string $newUrl): int
+    {
+        $oldQuoted = $this->db->getPdo()->quote($oldUrl);
+        $newQuoted = $this->db->getPdo()->quote($newUrl);
+        return $this->db->table($table)->update([
+            $column => $this->db->raw("REPLACE({$column}, {$oldQuoted}, {$newQuoted})")
+        ]);
+    }
+
     /**
      * Warn the user of the dangers of this operation.
      * Returns a boolean indicating if they've accepted the warnings.
diff --git a/tests/Commands/UpdateUrlCommandTest.php b/tests/Commands/UpdateUrlCommandTest.php
index 741040f1f..7043ce047 100644
--- a/tests/Commands/UpdateUrlCommandTest.php
+++ b/tests/Commands/UpdateUrlCommandTest.php
@@ -6,7 +6,7 @@ use Tests\TestCase;
 
 class UpdateUrlCommandTest extends TestCase
 {
-    public function test_update_url_command_updates_page_content()
+    public function test_command_updates_page_content()
     {
         $page = Page::query()->first();
         $page->html = '<a href="https://example.com/donkeys"></a>';
@@ -22,7 +22,7 @@ class UpdateUrlCommandTest extends TestCase
         ]);
     }
 
-    public function test_update_url_command_requires_valid_url()
+    public function test_command_requires_valid_url()
     {
         $badUrlMessage = "The given urls are expected to be full urls starting with http:// or https://";
         $this->artisan('bookstack:update-url //example.com https://cats.example.com')->expectsOutput($badUrlMessage);
@@ -33,14 +33,27 @@ class UpdateUrlCommandTest extends TestCase
         $this->artisan('bookstack:update-url https://cats.example.com');
     }
 
-    public function test_update_url_command_updates_settings()
+    public function test_command_updates_settings()
     {
         setting()->put('my-custom-item', 'https://example.com/donkey/cat');
-        $this->artisan('bookstack:update-url https://example.com https://cats.example.com')
-            ->expectsQuestion("This will search for \"https://example.com\" in your database and replace it with  \"https://cats.example.com\".\nAre you sure you want to proceed?", 'y')
-            ->expectsQuestion("This operation could cause issues if used incorrectly. Have you made a backup of your existing database?", 'y');
+        $this->runUpdate('https://example.com', 'https://cats.example.com');
 
         $settingVal = setting('my-custom-item');
         $this->assertEquals('https://cats.example.com/donkey/cat', $settingVal);
     }
+
+    public function test_command_updates_array_settings()
+    {
+        setting()->put('my-custom-array-item', [['name' => 'a https://example.com/donkey/cat url']]);
+        $this->runUpdate('https://example.com', 'https://cats.example.com');
+        $settingVal = setting('my-custom-array-item');
+        $this->assertEquals('a https://cats.example.com/donkey/cat url', $settingVal[0]['name']);
+    }
+
+    protected function runUpdate(string $oldUrl, string $newUrl)
+    {
+        $this->artisan("bookstack:update-url {$oldUrl} {$newUrl}")
+            ->expectsQuestion("This will search for \"{$oldUrl}\" in your database and replace it with  \"{$newUrl}\".\nAre you sure you want to proceed?", 'y')
+            ->expectsQuestion("This operation could cause issues if used incorrectly. Have you made a backup of your existing database?", 'y');
+    }
 }
\ No newline at end of file