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diff --git a/public/img/legacy/confused_smile.png b/public/img/legacy/confused_smile.png
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diff --git a/public/img/legacy/envelope.png b/public/img/legacy/envelope.png
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diff --git a/public/img/legacy/whatchutalkingabout_smile.png b/public/img/legacy/whatchutalkingabout_smile.png
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diff --git a/src/CoreBundle/Migrations/Schema/V200/Version20240924120200.php b/src/CoreBundle/Migrations/Schema/V200/Version20240924120200.php
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index 0000000000..1fadf7657a
--- /dev/null
+++ b/src/CoreBundle/Migrations/Schema/V200/Version20240924120200.php
@@ -0,0 +1,80 @@
+<?php
+
+declare(strict_types=1);
+
+/* For licensing terms, see /license.txt */
+
+namespace Chamilo\CoreBundle\Migrations\Schema\V200;
+
+use Chamilo\CoreBundle\Migrations\AbstractMigrationChamilo;
+use Doctrine\DBAL\Schema\Schema;
+
+final class Version20240924120200 extends AbstractMigrationChamilo
+{
+    public function getDescription(): string
+    {
+        return 'Update HTML content blocks to replace old CKEditor image paths with new ones and convert .gif references to .png';
+    }
+
+    public function up(Schema $schema): void
+    {
+        $this->entityManager->clear();
+
+        // Define the content fields to update
+        $updateConfigurations = [
+            ['table' => 'c_tool_intro', 'field' => 'intro_text'],
+            ['table' => 'c_course_description', 'field' => 'content'],
+            ['table' => 'c_quiz', 'fields' => ['description', 'text_when_finished']],
+            ['table' => 'c_quiz_question', 'fields' => ['description', 'question']],
+            ['table' => 'c_quiz_answer', 'fields' => ['answer', 'comment']],
+            ['table' => 'c_student_publication', 'field' => 'description'],
+            ['table' => 'c_student_publication_comment', 'field' => 'comment'],
+            ['table' => 'c_forum_post', 'field' => 'post_text'],
+            ['table' => 'c_glossary', 'field' => 'description'],
+            ['table' => 'c_survey', 'fields' => ['title', 'subtitle']],
+            ['table' => 'c_survey_question', 'fields' => ['survey_question', 'survey_question_comment']],
+            ['table' => 'c_survey_question_option', 'field' => 'option_text'],
+        ];
+
+        foreach ($updateConfigurations as $config) {
+            $this->updateContent($config);
+        }
+    }
+
+    private function updateContent(array $config): void
+    {
+        $fields = isset($config['field']) ? [$config['field']] : $config['fields'] ?? [];
+
+        foreach ($fields as $field) {
+            $sql = "SELECT iid, {$field} FROM {$config['table']}";
+            $result = $this->connection->executeQuery($sql);
+            $items = $result->fetchAllAssociative();
+
+            foreach ($items as $item) {
+                $originalText = $item[$field];
+                if (!empty($originalText)) {
+                    $updatedText = $this->replaceGifWithPng($originalText);
+                    if ($originalText !== $updatedText) {
+                        $updateSql = "UPDATE {$config['table']} SET {$field} = :newText WHERE iid = :id";
+                        $this->connection->executeQuery($updateSql, ['newText' => $updatedText, 'id' => $item['iid']]);
+                    }
+                }
+            }
+        }
+    }
+
+    private function replaceGifWithPng(string $content): string
+    {
+        $pattern = '/(src=["\'])(https?:\/\/[^\/]+\/)?(\/?web\/assets\/ckeditor\/plugins\/smiley\/images\/([a-zA-Z0-9_\-]+))\.(gif|png)(["\'])/i';
+
+        $content = preg_replace_callback($pattern, function ($matches) {
+            $prefix = $matches[1];
+            $filename = $matches[4];
+            $extension = 'png';
+
+            return "{$prefix}/img/legacy/{$filename}.{$extension}{$matches[6]}";
+        }, $content);
+
+        return $content;
+    }
+}