diff --git a/_config/extensions.yml b/_config/extensions.yml
index 3e243dccb..5ec2910c4 100644
--- a/_config/extensions.yml
+++ b/_config/extensions.yml
@@ -4,3 +4,6 @@ Name: userformsextensions
 SilverStripe\UserForms\Model\UserDefinedForm:
   extensions:
     UpgradePolymorphicExtension: SilverStripe\UserForms\Extension\UpgradePolymorphicExtension
+SilverStripe\Assets\File:
+  extensions:
+    - SilverStripe\UserForms\Extension\UserFormFileExtension
diff --git a/code/Control/UserDefinedFormController.php b/code/Control/UserDefinedFormController.php
index 692f5ca8f..a14b21ecc 100644
--- a/code/Control/UserDefinedFormController.php
+++ b/code/Control/UserDefinedFormController.php
@@ -21,6 +21,7 @@
 use SilverStripe\ORM\ValidationException;
 use SilverStripe\ORM\ValidationResult;
 use SilverStripe\Security\Security;
+use SilverStripe\UserForms\Extension\UserFormFileExtension;
 use SilverStripe\UserForms\Form\UserForm;
 use SilverStripe\UserForms\Model\EditableFormField;
 use SilverStripe\UserForms\Model\EditableFormField\EditableFileField;
@@ -269,6 +270,7 @@ public function process($data, $form)
                         /** @var AssetContainer|File $file */
                         $file = $upload->getFile();
                         $file->ShowInSearch = 0;
+                        $file->UserFormUpload = UserFormFileExtension::USER_FORM_UPLOAD_TRUE;
                         $file->write();
 
                         // generate image thumbnail to show in asset-admin
diff --git a/code/Extension/UserFormFileExtension.php b/code/Extension/UserFormFileExtension.php
new file mode 100644
index 000000000..75f30a68a
--- /dev/null
+++ b/code/Extension/UserFormFileExtension.php
@@ -0,0 +1,80 @@
+<?php
+
+namespace SilverStripe\UserForms\Extension;
+
+use SilverStripe\Assets\File;
+use SilverStripe\Assets\Folder;
+use SilverStripe\Core\Convert;
+use SilverStripe\ORM\DataExtension;
+use SilverStripe\ORM\DataObject;
+use SilverStripe\ORM\Queries\SQLUpdate;
+use SilverStripe\UserForms\Control\UserDefinedFormController;
+use SilverStripe\UserForms\Model\Submission\SubmittedFileField;
+use SilverStripe\Versioned\Versioned;
+
+/**
+ * @method File SubmittedFileField
+ */
+class UserFormFileExtension extends DataExtension
+{
+
+    public const USER_FORM_UPLOAD_UNKNOWN = null;
+
+    public const USER_FORM_UPLOAD_FALSE = 'f';
+
+    public const USER_FORM_UPLOAD_TRUE = 't';
+
+    private static $db = [
+        'UserFormUpload' => "Enum('f, t', null)",
+    ];
+
+    private static $belongs_to = [
+        'SubmittedFileField' => SubmittedFileField::class
+    ];
+
+    /**
+     * Check if the file is associated with a userform submission
+     * Save the result in the database as a tri-state for two reasons:
+     * a) performance - prevent the need for an extra DB query
+     * b) if in the future the UserForm submission is deleted and the uploaded file is not (file is orphaned),
+     *    then it is still recorded that the file was originally uploaded from a userform submission
+     *
+     * @param bool $value
+     * @see File::isTrackedFormUpload(), UserDefinedFormController::process()
+     */
+    public function updateTrackedFormUpload(&$value): void
+    {
+        /** @var File|Versioned|UserFormFileExtension $file */
+        $file = $this->owner;
+        if ($file->UserFormUpload != self::USER_FORM_UPLOAD_UNKNOWN) {
+            $value = $file->UserFormUpload == self::USER_FORM_UPLOAD_TRUE;
+            return;
+        }
+        if ($file->ClassName == Folder::class) {
+            $value = false;
+        } else {
+            $value = $file->SubmittedFileField()->exists();
+        }
+        $this->updateDB($value);
+    }
+
+    /**
+     * Update File.UserFormUpload draft table without altering File.LastEdited
+     *
+     * @param bool $value
+     */
+    private function updateDB(bool $value): void
+    {
+        if (!$this->owner->isInDB()) {
+            return;
+        }
+        $tableName = Convert::raw2sql(DataObject::getSchema()->tableName(File::class));
+        $column = 'UserFormUpload';
+        $enumVal = $value ? self::USER_FORM_UPLOAD_TRUE : self::USER_FORM_UPLOAD_FALSE;
+        SQLUpdate::create()
+            ->setTable(sprintf('"%s"', $tableName))
+            ->addWhere(['"ID" = ?' => [$this->owner->ID]])
+            ->addAssignments([sprintf('"%s"', $column) => $enumVal])
+            ->execute();
+    }
+}
diff --git a/composer.json b/composer.json
index c2a17ac6e..22a9811c0 100644
--- a/composer.json
+++ b/composer.json
@@ -30,6 +30,7 @@
         }
     ],
     "require": {
+        "php": ">=7.1",
         "silverstripe/cms": "^4.0",
         "symbiote/silverstripe-gridfieldextensions": "^3.1",
         "silverstripe/segment-field": "^2.0",
diff --git a/tests/Extension/UserFormFileExtensionTest.php b/tests/Extension/UserFormFileExtensionTest.php
new file mode 100644
index 000000000..13af9f31d
--- /dev/null
+++ b/tests/Extension/UserFormFileExtensionTest.php
@@ -0,0 +1,49 @@
+<?php
+
+namespace SilverStripe\UserForms\Tests\Extension;
+
+use SilverStripe\Assets\File;
+use SilverStripe\Dev\SapphireTest;
+use SilverStripe\UserForms\Model\Submission\SubmittedFileField;
+use SilverStripe\UserForms\Extension\UserFormFileExtension;
+
+class UserFormFileExtensionTest extends SapphireTest
+{
+    protected $usesDatabase = true;
+
+    public function testUpdateIsUserFormUploadFalse()
+    {
+        $file = File::create();
+        $file->write();
+        $this->assertNull($file->UserFormUpload);
+
+        $value = true;
+        $file->invokeWithExtensions('updateTrackedFormUpload', $value);
+        $this->assertFalse($value);
+
+        // refresh DataObject to get latest DB changes
+        $file = File::get()->byID($file->ID);
+
+        $this->assertEquals(UserFormFileExtension::USER_FORM_UPLOAD_FALSE, $file->UserFormUpload);
+    }
+
+    public function testUpdateIsUserFormUploadTrue()
+    {
+        $file = File::create();
+        $file->write();
+        $this->assertNull($file->UserFormUpload);
+
+        $submittedFileField = SubmittedFileField::create();
+        $submittedFileField->UploadedFileID = $file->ID;
+        $submittedFileField->write();
+
+        $value = false;
+        $file->invokeWithExtensions('updateTrackedFormUpload', $value);
+        $this->assertTrue($value);
+
+        // refresh DataObject to get latest DB changes
+        $file = File::get()->byID($file->ID);
+
+        $this->assertEquals(UserFormFileExtension::USER_FORM_UPLOAD_TRUE, $file->UserFormUpload);
+    }
+}