diff --git a/webapp/migrations/Version20240917113927.php b/webapp/migrations/Version20240917113927.php
new file mode 100755
index 0000000000..9eea7036b9
--- /dev/null
+++ b/webapp/migrations/Version20240917113927.php
@@ -0,0 +1,31 @@
+<?php
+
+declare(strict_types=1);
+
+namespace DoctrineMigrations;
+
+use Doctrine\DBAL\Schema\Schema;
+use Doctrine\Migrations\AbstractMigration;
+
+final class Version20240917113927 extends AbstractMigration
+{
+    public function getDescription(): string
+    {
+        return 'Adding executable bit to problem attachments.';
+    }
+
+    public function up(Schema $schema): void
+    {
+        $this->addSql('ALTER TABLE problem_attachment_content ADD is_executable TINYINT(1) DEFAULT 0 NOT NULL COMMENT \'Whether this file gets an executable bit.\'');
+    }
+
+    public function down(Schema $schema): void
+    {
+        $this->addSql('ALTER TABLE problem_attachment_content DROP is_executable');
+    }
+
+    public function isTransactional(): bool
+    {
+        return false;
+    }
+}
diff --git a/webapp/src/Entity/ProblemAttachmentContent.php b/webapp/src/Entity/ProblemAttachmentContent.php
index d961a526e6..7dd60b2c83 100644
--- a/webapp/src/Entity/ProblemAttachmentContent.php
+++ b/webapp/src/Entity/ProblemAttachmentContent.php
@@ -3,6 +3,7 @@
 namespace App\Entity;
 
 use Doctrine\ORM\Mapping as ORM;
+use JMS\Serializer\Annotation as Serializer;
 
 #[ORM\Entity]
 #[ORM\Table(options: [
@@ -25,6 +26,10 @@ class ProblemAttachmentContent
     #[ORM\Column(type: 'blobtext', options: ['comment' => 'Attachment content'])]
     private string $content;
 
+    #[ORM\Column(options: ['comment' => 'Whether this file gets an executable bit.', 'default' => 0])]
+    #[Serializer\Exclude]
+    private bool $isExecutable = false;
+
     public function getAttachment(): ProblemAttachment
     {
         return $this->attachment;
@@ -48,4 +53,15 @@ public function setContent(string $content): self
 
         return $this;
     }
+
+    public function setIsExecutable(bool $isExecutable): ProblemAttachmentContent
+    {
+        $this->isExecutable = $isExecutable;
+        return $this;
+    }
+
+    public function isExecutable(): bool
+    {
+        return $this->isExecutable;
+    }
 }
diff --git a/webapp/src/Service/DOMJudgeService.php b/webapp/src/Service/DOMJudgeService.php
index 423f7b3f96..744bfe4201 100644
--- a/webapp/src/Service/DOMJudgeService.php
+++ b/webapp/src/Service/DOMJudgeService.php
@@ -892,6 +892,14 @@ public function getSamplesZipForContest(Contest $contest): StreamedResponse
             foreach ($problem->getProblem()->getAttachments() as $attachment) {
                 $filename = sprintf('%s/attachments/%s', $problem->getShortname(), $attachment->getName());
                 $zip->addFromString($filename, $attachment->getContent()->getContent());
+                if ($attachment->getContent()->isExecutable()) {
+                    // 100755 = regular file, executable
+                    $zip->setExternalAttributesName(
+                        $filename,
+                        ZipArchive::OPSYS_UNIX,
+                        octdec('100755') << 16
+                    );
+                }
             }
         }
 
diff --git a/webapp/src/Service/ImportProblemService.php b/webapp/src/Service/ImportProblemService.php
index 8b58db4f46..64d5059137 100644
--- a/webapp/src/Service/ImportProblemService.php
+++ b/webapp/src/Service/ImportProblemService.php
@@ -539,6 +539,14 @@ public function importZippedProblem(
                 continue;
             }
 
+            // In doubt make files executable, but try to read it from the zip file.
+            $executableBit = true;
+            if ($zip->getExternalAttributesIndex($j, $opsys, $attr)
+                && $opsys==ZipArchive::OPSYS_UNIX
+                && (($attr >> 16) & 0100) === 0) {
+                $executableBit = false;
+            }
+
             $name = basename($filename);
 
             $fileParts = explode('.', $name);
@@ -558,6 +566,10 @@ public function importZippedProblem(
                     $messages['info'][] = sprintf("Updated attachment '%s'", $name);
                     $numAttachments++;
                 }
+                if ($executableBit !== $attachmentContent->isExecutable()) {
+                    $attachmentContent->setIsExecutable($executableBit);
+                    $messages['info'][] = sprintf("Updated executable bit of attachment '%s'", $name);
+                }
             } else {
                 $attachment = new ProblemAttachment();
                 $attachmentContent = new ProblemAttachmentContent();
@@ -567,7 +579,9 @@ public function importZippedProblem(
                     ->setType($type)
                     ->setContent($attachmentContent);
 
-                $attachmentContent->setContent($content);
+                $attachmentContent
+                    ->setContent($content)
+                    ->setIsExecutable($executableBit);
 
                 $this->em->persist($attachment);