diff --git a/.idea/libraries/jsoup.xml b/.idea/libraries/jsoup.xml
index ad4c47fe6d58..5c8a9ee9c537 100644
--- a/.idea/libraries/jsoup.xml
+++ b/.idea/libraries/jsoup.xml
@@ -1,9 +1,9 @@
 <component name="libraryTable">
   <library name="jsoup" type="repository">
-    <properties maven-id="org.jsoup:jsoup:1.19.1">
+    <properties maven-id="org.jsoup:jsoup:1.21.2">
       <verification>
-        <artifact url="file://$MAVEN_REPOSITORY$/org/jsoup/jsoup/1.19.1/jsoup-1.19.1.jar">
-          <sha256sum>7b850eb00f2f77f606a343b2e4effe4107f3c1faa183729d85fbe16baf606096</sha256sum>
+        <artifact url="file://$MAVEN_REPOSITORY$/org/jsoup/jsoup/1.21.2/jsoup-1.21.2.jar">
+          <sha256sum>f05496e255734759f0d4b5632da7b24f81313147c78c69e90ad045d096191344</sha256sum>
         </artifact>
       </verification>
     </properties>
@@ -11,13 +11,13 @@
       <root url="file://$PROJECT_DIR$/lib/annotations/jsoup" />
     </ANNOTATIONS>
     <CLASSES>
-      <root url="jar://$MAVEN_REPOSITORY$/org/jsoup/jsoup/1.19.1/jsoup-1.19.1.jar!/" />
+      <root url="jar://$MAVEN_REPOSITORY$/org/jsoup/jsoup/1.21.2/jsoup-1.21.2.jar!/" />
     </CLASSES>
     <JAVADOC>
-      <root url="jar://$MAVEN_REPOSITORY$/org/jsoup/jsoup/1.19.1/jsoup-1.19.1-javadoc.jar!/" />
+      <root url="jar://$MAVEN_REPOSITORY$/org/jsoup/jsoup/1.21.2/jsoup-1.21.2-javadoc.jar!/" />
     </JAVADOC>
     <SOURCES>
-      <root url="jar://$MAVEN_REPOSITORY$/org/jsoup/jsoup/1.19.1/jsoup-1.19.1-sources.jar!/" />
+      <root url="jar://$MAVEN_REPOSITORY$/org/jsoup/jsoup/1.21.2/jsoup-1.21.2-sources.jar!/" />
     </SOURCES>
   </library>
 </component>
\ No newline at end of file
diff --git a/java/java-tests/testSrc/com/intellij/java/codeInsight/JavaDocumentationTest.kt b/java/java-tests/testSrc/com/intellij/java/codeInsight/JavaDocumentationTest.kt
index 47f6358465de..29df96e65f29 100644
--- a/java/java-tests/testSrc/com/intellij/java/codeInsight/JavaDocumentationTest.kt
+++ b/java/java-tests/testSrc/com/intellij/java/codeInsight/JavaDocumentationTest.kt
@@ -14,6 +14,7 @@ import com.intellij.testFramework.fixtures.LightJavaCodeInsightFixtureTestCase
 import com.intellij.util.concurrency.AppExecutorUtil
 import com.intellij.util.ui.UIUtil
 import junit.framework.TestCase
+import org.assertj.core.api.Assertions.assertThat
 import java.util.concurrent.Callable
 import kotlin.test.assertContains
 import kotlin.test.assertFails
@@ -327,8 +328,7 @@ class JavaDocumentationTest : LightJavaCodeInsightFixtureTestCase() {
       }
 
       // Here we check that the covering module (SDK in this case) is rendered in decorated info
-      assertTrue(
-        component.decoratedText.contains("<div class=\"bottom\"><icon src=\"AllIcons.Nodes.PpLibFolder\" />&nbsp;&lt; java 1.7 &gt;</div>"))
+      assertThat(component.decoratedText).contains("""<div class="bottom"><icon src="AllIcons.Nodes.PpLibFolder"></icon>&nbsp;&lt; java 1.7 &gt;</div>""")
       return@getDocumentationText null
     }
   }
diff --git a/lib/BUILD.bazel b/lib/BUILD.bazel
index 71dd811893fd..c91cef62f864 100644
--- a/lib/BUILD.bazel
+++ b/lib/BUILD.bazel
@@ -3059,8 +3059,8 @@ jvm_import(
 
 jvm_import(
   name = "jsoup",
-  jar = "@jsoup-1_19_1_http//file",
-  source_jar = "@jsoup-1_19_1-sources_http//file",
+  jar = "@jsoup-1_21_2_http//file",
+  source_jar = "@jsoup-1_21_2-sources_http//file",
   visibility = ["//visibility:public"]
 )
 
diff --git a/lib/MODULE.bazel b/lib/MODULE.bazel
index ca6a35238c10..2f5b9967114f 100644
--- a/lib/MODULE.bazel
+++ b/lib/MODULE.bazel
@@ -4354,17 +4354,17 @@ http_file(
 )
 
 http_file(
-  name = "jsoup-1_19_1_http",
-  url = "https://cache-redirector.jetbrains.com/repo1.maven.org/maven2/org/jsoup/jsoup/1.19.1/jsoup-1.19.1.jar",
-  sha256 = "7b850eb00f2f77f606a343b2e4effe4107f3c1faa183729d85fbe16baf606096",
-  downloaded_file_path = "jsoup-1.19.1.jar"
+  name = "jsoup-1_21_2_http",
+  url = "https://cache-redirector.jetbrains.com/repo1.maven.org/maven2/org/jsoup/jsoup/1.21.2/jsoup-1.21.2.jar",
+  sha256 = "f05496e255734759f0d4b5632da7b24f81313147c78c69e90ad045d096191344",
+  downloaded_file_path = "jsoup-1.21.2.jar"
 )
 
 http_file(
-  name = "jsoup-1_19_1-sources_http",
-  url = "https://cache-redirector.jetbrains.com/repo1.maven.org/maven2/org/jsoup/jsoup/1.19.1/jsoup-1.19.1-sources.jar",
-  sha256 = "54838f69298a69e4b1f5f45b659f5206978b41bcc2a4e13438220f1a1d601ab1",
-  downloaded_file_path = "jsoup-1.19.1-sources.jar"
+  name = "jsoup-1_21_2-sources_http",
+  url = "https://cache-redirector.jetbrains.com/repo1.maven.org/maven2/org/jsoup/jsoup/1.21.2/jsoup-1.21.2-sources.jar",
+  sha256 = "2cbf6a46b1af6bace17f25b3bedb1b0e5d56882083918c30c27608e188870a73",
+  downloaded_file_path = "jsoup-1.21.2-sources.jar"
 )
 
 http_file(
diff --git a/plugins/markdown/core/src/org/intellij/plugins/markdown/ui/preview/jcef/impl/IncrementalDOMBuilder.kt b/plugins/markdown/core/src/org/intellij/plugins/markdown/ui/preview/jcef/impl/IncrementalDOMBuilder.kt
index 654159c4e3e9..7df415ba5314 100644
--- a/plugins/markdown/core/src/org/intellij/plugins/markdown/ui/preview/jcef/impl/IncrementalDOMBuilder.kt
+++ b/plugins/markdown/core/src/org/intellij/plugins/markdown/ui/preview/jcef/impl/IncrementalDOMBuilder.kt
@@ -18,6 +18,9 @@ import org.jsoup.nodes.Comment
 import org.jsoup.nodes.DataNode
 import org.jsoup.nodes.Node
 import org.jsoup.nodes.TextNode
+import org.jsoup.parser.Parser
+import org.jsoup.parser.Tag
+import org.jsoup.parser.TagSet
 import java.net.URLDecoder
 import java.nio.charset.Charset
 
@@ -29,7 +32,7 @@ class IncrementalDOMBuilder(
   private val fileSchemeResourceProcessor: ResourceProvider? = null,
 ) {
 
-  private val document = Jsoup.parse(html)
+  private val document = Jsoup.parse(html, createSelfClosingSpanAwareParser())
   private val builder = StringBuilder()
 
   fun generateRenderClosure(): String {
@@ -163,3 +166,11 @@ class IncrementalDOMBuilder(
     }
   }
 }
+
+// https://jsoup.org/news/release-1.20.1
+private fun createSelfClosingSpanAwareParser(): Parser {
+  val tags = TagSet.Html()
+  val span = tags.valueOf("span", Parser.NamespaceHtml)
+  span.set(Tag.SelfClose)
+  return Parser.htmlParser().tagSet(tags)
+}