diff --git a/src/Configuration/EmailConfiguration.php b/src/Configuration/EmailConfiguration.php
index 639fa99..8ee4671 100644
--- a/src/Configuration/EmailConfiguration.php
+++ b/src/Configuration/EmailConfiguration.php
@@ -32,7 +32,7 @@ public function modify(Container $container)
             return new SesClient($container['ymir_http_client'], $container['cloud_provider_key'], $container['cloud_provider_region'], $container['cloud_provider_secret']);
         });
         $container['email'] = function (Container $container) {
-            return new Email($container['event_manager'], $container['default_email_from'], $container['phpmailer'], $container['blog_charset']);
+            return new Email($container['event_manager'], $container['default_email_from'], $container['file_manager'], $container['phpmailer'], $container['blog_charset']);
         };
     }
 }
diff --git a/src/Email/Email.php b/src/Email/Email.php
index c1450fb..61cbfc7 100644
--- a/src/Email/Email.php
+++ b/src/Email/Email.php
@@ -13,7 +13,9 @@
 
 namespace Ymir\Plugin\Email;
 
+use Ymir\Plugin\Attachment\AttachmentFileManager;
 use Ymir\Plugin\EventManagement\EventManager;
+use Ymir\Plugin\Support\Collection;
 
 class Email
 {
@@ -45,6 +47,13 @@ class Email
      */
     private $eventManager;
 
+    /**
+     * The attachment file manager.
+     *
+     * @var AttachmentFileManager
+     */
+    private $fileManager;
+
     /**
      * WordPress PHPMailer object.
      *
@@ -55,12 +64,13 @@ class Email
     /**
      * Constructor.
      */
-    public function __construct(EventManager $eventManager, string $defaultFromAddress, \PHPMailer $mailer, string $defaultCharset = 'UTF-8', string $defaultContentType = 'text/plain')
+    public function __construct(EventManager $eventManager, string $defaultFromAddress, AttachmentFileManager $fileManager, \PHPMailer $mailer, string $defaultCharset = 'UTF-8', string $defaultContentType = 'text/plain')
     {
         $this->defaultCharset = $defaultCharset;
         $this->defaultContentType = $defaultContentType;
         $this->defaultFromAddress = $defaultFromAddress;
         $this->eventManager = $eventManager;
+        $this->fileManager = $fileManager;
         $this->mailer = $mailer;
 
         // Remove some of the default values so we can check if they were set and passed through the WordPress filters
@@ -80,9 +90,15 @@ public function attachments($attachments)
             throw new \InvalidArgumentException('"attachments" argument must be an array or a string');
         }
 
-        foreach ($attachments as $attachment) {
+        (new Collection($attachments))->map(function (string $attachment) {
+            if ($this->fileManager->isInUploadsDirectory($attachment)) {
+                $attachment = $this->fileManager->copyToTempDirectory($attachment);
+            }
+
+            return $attachment;
+        })->each(function (string $attachment) {
             $this->mailer->addAttachment($attachment);
-        }
+        });
     }
 
     /**
diff --git a/tests/Unit/Email/EmailTest.php b/tests/Unit/Email/EmailTest.php
index 2f28ef7..654c9bf 100644
--- a/tests/Unit/Email/EmailTest.php
+++ b/tests/Unit/Email/EmailTest.php
@@ -14,6 +14,7 @@
 namespace Ymir\Plugin\Tests\Unit\Email;
 
 use Ymir\Plugin\Email\Email;
+use Ymir\Plugin\Tests\Mock\AttachmentFileManagerMockTrait;
 use Ymir\Plugin\Tests\Mock\EventManagerMockTrait;
 use Ymir\Plugin\Tests\Mock\PHPMailerMockTrait;
 use Ymir\Plugin\Tests\Unit\TestCase;
@@ -23,9 +24,40 @@
  */
 class EmailTest extends TestCase
 {
+    use AttachmentFileManagerMockTrait;
     use EventManagerMockTrait;
     use PHPMailerMockTrait;
 
+    public function testAttachmentsCopiesUploadFilesToTmpDirectory()
+    {
+        $fileManager = $this->getAttachmentFileManagerMock();
+        $phpmailer = $this->getPHPMailerMock();
+
+        $fileManager->expects($this->exactly(2))
+                    ->method('isInUploadsDirectory')
+                    ->withConsecutive(
+                        [$this->identicalTo('attachment1')],
+                        [$this->identicalTo('attachment2')]
+                    )
+                    ->willReturnOnConsecutiveCalls(false, true);
+
+        $fileManager->expects($this->once())
+                    ->method('copyToTempDirectory')
+                    ->with($this->identicalTo('attachment2'))
+                    ->willReturn('/tmp/attachment2');
+
+        $phpmailer->expects($this->exactly(2))
+                  ->method('addAttachment')
+                  ->withConsecutive(
+                      [$this->identicalTo('attachment1')],
+                      [$this->identicalTo('/tmp/attachment2')]
+                  );
+
+        $email = new Email($this->getEventManagerMock(), 'from_address', $fileManager, $phpmailer);
+
+        $email->attachments(['attachment1', 'attachment2']);
+    }
+
     public function testAttachmentsWithArray()
     {
         $phpmailer = $this->getPHPMailerMock();
@@ -37,7 +69,7 @@ public function testAttachmentsWithArray()
                       [$this->identicalTo('attachment2')]
                   );
 
-        $email = new Email($this->getEventManagerMock(), 'from_address', $phpmailer);
+        $email = new Email($this->getEventManagerMock(), 'from_address', $this->getAttachmentFileManagerMock(), $phpmailer);
 
         $email->attachments(['attachment1', 'attachment2']);
     }
@@ -47,7 +79,7 @@ public function testAttachmentsWithInvalidArgument()
         $this->expectException(\InvalidArgumentException::class);
         $this->expectExceptionMessage('"attachments" argument must be an array or a string');
 
-        $email = new Email($this->getEventManagerMock(), 'from_address', $this->getPHPMailerMock());
+        $email = new Email($this->getEventManagerMock(), 'from_address', $this->getAttachmentFileManagerMock(), $this->getPHPMailerMock());
 
         $email->attachments(new \stdClass());
     }
@@ -63,7 +95,7 @@ public function testAttachmentsWithString()
                       [$this->identicalTo('attachment2')]
                   );
 
-        $email = new Email($this->getEventManagerMock(), 'from_address', $phpmailer);
+        $email = new Email($this->getEventManagerMock(), 'from_address', $this->getAttachmentFileManagerMock(), $phpmailer);
 
         $email->attachments("attachment1\r\nattachment2");
     }
@@ -79,7 +111,7 @@ public function testBccWithArray()
                       [$this->identicalTo('foo@bar.com'), $this->identicalTo('Foo')]
                   );
 
-        $email = new Email($this->getEventManagerMock(), 'from_address', $phpmailer);
+        $email = new Email($this->getEventManagerMock(), 'from_address', $this->getAttachmentFileManagerMock(), $phpmailer);
 
         $email->bcc(['test@test.com', 'Foo <foo@bar.com>']);
     }
@@ -89,7 +121,7 @@ public function testBccWithInvalidArgument()
         $this->expectException(\InvalidArgumentException::class);
         $this->expectExceptionMessage('"addresses" argument must be an array or a string');
 
-        $email = new Email($this->getEventManagerMock(), 'from_address', $this->getPHPMailerMock());
+        $email = new Email($this->getEventManagerMock(), 'from_address', $this->getAttachmentFileManagerMock(), $this->getPHPMailerMock());
 
         $email->bcc(new \stdClass());
     }
@@ -105,7 +137,7 @@ public function testBccWithString()
                       [$this->identicalTo('foo@bar.com'), $this->identicalTo('Foo')]
                   );
 
-        $email = new Email($this->getEventManagerMock(), 'from_address', $phpmailer);
+        $email = new Email($this->getEventManagerMock(), 'from_address', $this->getAttachmentFileManagerMock(), $phpmailer);
 
         $email->bcc('test@test.com, Foo <foo@bar.com>');
     }
@@ -120,7 +152,7 @@ public function testCharset()
                      ->with($this->identicalTo('wp_mail_charset'), $this->identicalTo('UTF-8'))
                      ->willReturn('filtered_UTF-8');
 
-        (new Email($eventManager, 'from_address', $phpmailer))->charset('UTF-8');
+        (new Email($eventManager, 'from_address', $this->getAttachmentFileManagerMock(), $phpmailer))->charset('UTF-8');
 
         $this->assertSame('filtered_UTF-8', $phpmailer->CharSet);
     }
@@ -132,7 +164,7 @@ public function testConstructorRemovesValues()
         $this->assertNotSame('', $phpmailer->CharSet);
         $this->assertNotSame('', $phpmailer->ContentType);
 
-        $email = new Email($this->getEventManagerMock(), 'from_address', $phpmailer);
+        $email = new Email($this->getEventManagerMock(), 'from_address', $this->getAttachmentFileManagerMock(), $phpmailer);
 
         $this->assertSame('', $phpmailer->CharSet);
         $this->assertSame('', $phpmailer->ContentType);
@@ -152,7 +184,7 @@ public function testContentTypeHtml()
                      ->with($this->identicalTo('wp_mail_content_type'), $this->identicalTo('text/html'))
                      ->willReturn('text/html');
 
-        (new Email($eventManager, 'from_address', $phpmailer))->contentType('text/html');
+        (new Email($eventManager, 'from_address', $this->getAttachmentFileManagerMock(), $phpmailer))->contentType('text/html');
 
         $this->assertSame('text/html', $phpmailer->ContentType);
     }
@@ -171,7 +203,7 @@ public function testContentTypeNotHtml()
                      ->with($this->identicalTo('wp_mail_content_type'), $this->identicalTo('content_type'))
                      ->willReturn('filtered_content_type');
 
-        (new Email($eventManager, 'from_address', $phpmailer))->contentType('content_type');
+        (new Email($eventManager, 'from_address', $this->getAttachmentFileManagerMock(), $phpmailer))->contentType('content_type');
 
         $this->assertSame('filtered_content_type', $phpmailer->ContentType);
     }
@@ -193,7 +225,7 @@ public function testFromWithDefaultNAme()
                   ->method('setFrom')
                   ->with($this->identicalTo('filtered_foo@bar.com'), $this->identicalTo('filtered_WordPress'), $this->identicalTo(false));
 
-        (new Email($eventManager, 'from_address', $phpmailer))->from('foo@bar.com');
+        (new Email($eventManager, 'from_address', $this->getAttachmentFileManagerMock(), $phpmailer))->from('foo@bar.com');
     }
 
     public function testHeadersWithArray()
@@ -222,7 +254,7 @@ public function testHeadersWithArray()
                   ->method('isHtml')
                   ->with($this->identicalTo(false));
 
-        (new Email($eventManager, 'from_address', $phpmailer))->headers([
+        (new Email($eventManager, 'from_address', $this->getAttachmentFileManagerMock(), $phpmailer))->headers([
             'From: test@test.com',
             'Cc: Foo <foo@bar.com>',
             'Content-Type: content_type',
@@ -248,7 +280,7 @@ public function testHeadersWithContentTypeAndCharset()
                   ->method('isHtml')
                   ->with($this->identicalTo(false));
 
-        (new Email($eventManager, 'from_address', $phpmailer))->headers([
+        (new Email($eventManager, 'from_address', $this->getAttachmentFileManagerMock(), $phpmailer))->headers([
             'Content-Type: content_type;charset=foo_charset',
         ]);
     }
@@ -258,7 +290,7 @@ public function testHeadersWithInvalidArgument()
         $this->expectException(\InvalidArgumentException::class);
         $this->expectExceptionMessage('"headers" argument must be an array or a string');
 
-        $email = new Email($this->getEventManagerMock(), 'from_address', $this->getPHPMailerMock());
+        $email = new Email($this->getEventManagerMock(), 'from_address', $this->getAttachmentFileManagerMock(), $this->getPHPMailerMock());
 
         $email->headers(new \stdClass());
     }
@@ -280,7 +312,7 @@ public function testHeadersWithMultipartContentType()
                    ->method('isHtml')
                    ->with($this->identicalTo(false));
 
-        (new Email($eventManager, 'from_address', $phpmailer))->headers([
+        (new Email($eventManager, 'from_address', $this->getAttachmentFileManagerMock(), $phpmailer))->headers([
             'Content-Type: multipart/mixed; boundary="----=_Part_4892_25692638.1192452070893"',
         ]);
     }
@@ -311,7 +343,7 @@ public function testHeadersWithString()
                   ->method('isHtml')
                   ->with($this->identicalTo(false));
 
-        (new Email($eventManager, 'from_address', $phpmailer))->headers("From: test@test.com\r\nCc: Foo <foo@bar.com>\r\nContent-Type: content_type\r\nHeader: Value\r\nX-Mailer: foo");
+        (new Email($eventManager, 'from_address', $this->getAttachmentFileManagerMock(), $phpmailer))->headers("From: test@test.com\r\nCc: Foo <foo@bar.com>\r\nContent-Type: content_type\r\nHeader: Value\r\nX-Mailer: foo");
     }
 
     public function testReplyToWithArray()
@@ -325,7 +357,7 @@ public function testReplyToWithArray()
                       [$this->identicalTo('foo@bar.com'), $this->identicalTo('Foo')]
                   );
 
-        $email = new Email($this->getEventManagerMock(), 'from_address', $phpmailer);
+        $email = new Email($this->getEventManagerMock(), 'from_address', $this->getAttachmentFileManagerMock(), $phpmailer);
 
         $email->replyTo(['test@test.com', 'Foo <foo@bar.com>']);
     }
@@ -335,7 +367,7 @@ public function testReplyToWithInvalidArgument()
         $this->expectException(\InvalidArgumentException::class);
         $this->expectExceptionMessage('"addresses" argument must be an array or a string');
 
-        $email = new Email($this->getEventManagerMock(), 'from_address', $this->getPHPMailerMock());
+        $email = new Email($this->getEventManagerMock(), 'from_address', $this->getAttachmentFileManagerMock(), $this->getPHPMailerMock());
 
         $email->replyTo(new \stdClass());
     }
@@ -351,7 +383,7 @@ public function testReplyToWithString()
                       [$this->identicalTo('foo@bar.com'), $this->identicalTo('Foo')]
                   );
 
-        $email = new Email($this->getEventManagerMock(), 'from_address', $phpmailer);
+        $email = new Email($this->getEventManagerMock(), 'from_address', $this->getAttachmentFileManagerMock(), $phpmailer);
 
         $email->replyTo('test@test.com, Foo <foo@bar.com>');
     }
@@ -360,7 +392,7 @@ public function testSubject()
     {
         $phpmailer = $this->getPHPMailerMock();
 
-        (new Email($this->getEventManagerMock(), 'from_address', $phpmailer))->subject('Foo subject');
+        (new Email($this->getEventManagerMock(), 'from_address', $this->getAttachmentFileManagerMock(), $phpmailer))->subject('Foo subject');
 
         $this->assertSame('Foo subject', $phpmailer->Subject);
     }
@@ -390,7 +422,7 @@ public function testToStringSetsDefaultValues()
                   ->method('getSentMIMEMessage')
                   ->willReturn('email');
 
-        $this->assertSame('email', (new Email($eventManager, 'from_address', $phpmailer))->toString());
+        $this->assertSame('email', (new Email($eventManager, 'from_address', $this->getAttachmentFileManagerMock(), $phpmailer))->toString());
     }
 
     public function testToWithArray()
@@ -404,7 +436,7 @@ public function testToWithArray()
                       [$this->identicalTo('foo@bar.com'), $this->identicalTo('Foo')]
                   );
 
-        $email = new Email($this->getEventManagerMock(), 'from_address', $phpmailer);
+        $email = new Email($this->getEventManagerMock(), 'from_address', $this->getAttachmentFileManagerMock(), $phpmailer);
 
         $email->to(['test@test.com', 'Foo <foo@bar.com>']);
     }
@@ -414,7 +446,7 @@ public function testToWithInvalidArgument()
         $this->expectException(\InvalidArgumentException::class);
         $this->expectExceptionMessage('"addresses" argument must be an array or a string');
 
-        $email = new Email($this->getEventManagerMock(), 'from_address', $this->getPHPMailerMock());
+        $email = new Email($this->getEventManagerMock(), 'from_address', $this->getAttachmentFileManagerMock(), $this->getPHPMailerMock());
 
         $email->to(new \stdClass());
     }
@@ -430,7 +462,7 @@ public function testToWithString()
                       [$this->identicalTo('foo@bar.com'), $this->identicalTo('Foo')]
                   );
 
-        $email = new Email($this->getEventManagerMock(), 'from_address', $phpmailer);
+        $email = new Email($this->getEventManagerMock(), 'from_address', $this->getAttachmentFileManagerMock(), $phpmailer);
 
         $email->to('test@test.com, Foo <foo@bar.com>');
     }