diff --git a/src/Conversion/FileConverter.php b/src/Conversion/FileConverter.php
index 54d3c025..f5ef347b 100644
--- a/src/Conversion/FileConverter.php
+++ b/src/Conversion/FileConverter.php
@@ -2,6 +2,7 @@
 
 namespace SilverStripe\Assets\Conversion;
 
+use SilverStripe\Assets\File;
 use SilverStripe\Assets\Storage\DBFile;
 
 /**
@@ -27,5 +28,5 @@ public function supportsConversion(string $fromExtension, string $toExtension, a
      * @param array $options Any options defined for this converter which should apply to the conversion.
      * @throws FileConverterException if invalid options are passed, or the conversion is not supported or fails.
      */
-    public function convert(DBFile $from, string $toExtension, array $options = []): DBFile;
+    public function convert(DBFile|File $from, string $toExtension, array $options = []): DBFile;
 }
diff --git a/src/Conversion/FileConverterManager.php b/src/Conversion/FileConverterManager.php
index 504d26c6..92236a99 100644
--- a/src/Conversion/FileConverterManager.php
+++ b/src/Conversion/FileConverterManager.php
@@ -2,6 +2,7 @@
 
 namespace SilverStripe\Assets\Conversion;
 
+use SilverStripe\Assets\File;
 use SilverStripe\Assets\Storage\DBFile;
 use SilverStripe\Core\Config\Configurable;
 use SilverStripe\Core\Injector\Injector;
@@ -27,7 +28,7 @@ class FileConverterManager
      * Note that if a converter supports the conversion generally but doesn't support these options, that converter will not be used.
      * @throws FileConverterException if the conversion failed or there were no converters available.
      */
-    public function convert(DBFile $from, string $toExtension, array $options = []): DBFile
+    public function convert(DBFile|File $from, string $toExtension, array $options = []): DBFile
     {
         $fromExtension = $from->getExtension();
         foreach (static::config()->get('converters') as $converterClass) {
diff --git a/src/Conversion/InterventionImageFileConverter.php b/src/Conversion/InterventionImageFileConverter.php
index 61b3920d..9bd8c207 100644
--- a/src/Conversion/InterventionImageFileConverter.php
+++ b/src/Conversion/InterventionImageFileConverter.php
@@ -4,6 +4,7 @@
 
 use Imagick;
 use Intervention\Image\Exception\ImageException;
+use SilverStripe\Assets\File;
 use SilverStripe\Assets\Image_Backend;
 use SilverStripe\Assets\InterventionBackend;
 use SilverStripe\Assets\Storage\AssetStore;
@@ -30,7 +31,7 @@ public function supportsConversion(string $fromExtension, string $toExtension, a
         return $this->supportedByIntervention($fromExtension, $backend) && $this->supportedByIntervention($toExtension, $backend);
     }
 
-    public function convert(DBFile $from, string $toExtension, array $options = []): DBFile
+    public function convert(DBFile|File $from, string $toExtension, array $options = []): DBFile
     {
         // Do some basic validation up front for things we know aren't supported
         $problems = $this->validateOptions($options);
diff --git a/src/ImageManipulation.php b/src/ImageManipulation.php
index 7b849070..ed1d1e09 100644
--- a/src/ImageManipulation.php
+++ b/src/ImageManipulation.php
@@ -721,13 +721,8 @@ public function ThumbnailURL($width, $height)
     public function Convert(string $toExtension): ?AssetContainer
     {
         $converter = Injector::inst()->get(FileConverterManager::class);
-        if ($this instanceof File) {
-            $from = $this->File;
-        } elseif ($this instanceof DBFile) {
-            $from = $this;
-        }
         try {
-            return $converter->convert($from, $toExtension);
+            return $converter->convert($this, $toExtension);
         } catch (FileConverterException $e) {
             /** @var LoggerInterface $logger */
             $logger = Injector::inst()->get(LoggerInterface::class . '.errorhandler');
diff --git a/tests/php/Conversion/FileConversionManagerTest/TestImageConverter.php b/tests/php/Conversion/FileConversionManagerTest/TestImageConverter.php
index 4a505e17..939cf962 100644
--- a/tests/php/Conversion/FileConversionManagerTest/TestImageConverter.php
+++ b/tests/php/Conversion/FileConversionManagerTest/TestImageConverter.php
@@ -15,9 +15,9 @@ public function supportsConversion(string $fromExtension, string $toExtension, a
         return in_array($fromExtension, $formats) && in_array($toExtension, $formats);
     }
 
-    public function convert(DBFile $from, string $toExtension, array $options = []): DBFile
+    public function convert(DBFile|File $from, string $toExtension, array $options = []): DBFile
     {
-        $result = clone $from;
+        $result = ($from instanceof File) ? clone $from->File : clone $from;
         $result->Filename = 'converted.' . $toExtension;
         return $result;
     }
diff --git a/tests/php/Conversion/FileConversionManagerTest/TestTxtToImageConverter.php b/tests/php/Conversion/FileConversionManagerTest/TestTxtToImageConverter.php
index 9a17993f..1ad729fe 100644
--- a/tests/php/Conversion/FileConversionManagerTest/TestTxtToImageConverter.php
+++ b/tests/php/Conversion/FileConversionManagerTest/TestTxtToImageConverter.php
@@ -15,9 +15,9 @@ public function supportsConversion(string $fromExtension, string $toExtension, a
         return strtolower($fromExtension) === 'txt' && in_array(strtolower($toExtension), $formats);
     }
 
-    public function convert(DBFile $from, string $toExtension, array $options = []): DBFile
+    public function convert(DBFile|File $from, string $toExtension, array $options = []): DBFile
     {
-        $result = clone $from;
+        $result = ($from instanceof File) ? clone $from->File : clone $from;
         $result->Filename = 'converted.' . $toExtension;
         return $result;
     }
diff --git a/tests/php/ImageManipulationTest.php b/tests/php/ImageManipulationTest.php
index 0f966f35..c872f113 100644
--- a/tests/php/ImageManipulationTest.php
+++ b/tests/php/ImageManipulationTest.php
@@ -7,6 +7,7 @@
 use Psr\Log\LoggerInterface;
 use SilverStripe\Assets\Conversion\FileConverterException;
 use SilverStripe\Assets\Conversion\FileConverterManager;
+use SilverStripe\Assets\Conversion\InterventionImageFileConverter;
 use Silverstripe\Assets\Dev\TestAssetStore;
 use SilverStripe\Assets\File;
 use SilverStripe\Assets\FilenameParsing\AbstractFileIDHelper;
@@ -604,4 +605,27 @@ public function testConvert(string $originalFileFixtureClass, string $originalFi
             $this->assertNull($result);
         }
     }
+
+    public function provideConvertChainWithLazyLoad(): array
+    {
+        return [
+            [true],
+            [false],
+        ];
+    }
+
+    /**
+     * @dataProvider provideConvertChainWithLazyLoad
+     */
+    public function testConvertChainWithLazyLoad(bool $lazyLoad): void
+    {
+        // Make sure we have a known set of converters for testing
+        FileConverterManager::config()->set('converters', [InterventionImageFileConverter::class]);
+        $file = $this->objFromFixture(Image::class, 'imageWithTitle');
+        /** @var DBFile */
+        $result = $file->LazyLoad($lazyLoad)->Convert('webp');
+        $this->assertSame($lazyLoad, $result->IsLazyLoaded());
+        $result = $file->Convert('webp')->LazyLoad($lazyLoad);
+        $this->assertSame($lazyLoad, $result->IsLazyLoaded());
+    }
 }