diff --git a/features/messages/impl/src/main/kotlin/io/element/android/features/messages/impl/timeline/factories/event/TimelineItemContentMessageFactory.kt b/features/messages/impl/src/main/kotlin/io/element/android/features/messages/impl/timeline/factories/event/TimelineItemContentMessageFactory.kt
index a3c8a1bb26..3d8467729a 100644
--- a/features/messages/impl/src/main/kotlin/io/element/android/features/messages/impl/timeline/factories/event/TimelineItemContentMessageFactory.kt
+++ b/features/messages/impl/src/main/kotlin/io/element/android/features/messages/impl/timeline/factories/event/TimelineItemContentMessageFactory.kt
@@ -9,7 +9,6 @@
 package io.element.android.features.messages.impl.timeline.factories.event
 
 import android.text.style.URLSpan
-import androidx.core.text.buildSpannedString
 import androidx.core.text.getSpans
 import androidx.core.text.toSpannable
 import dev.zacsweers.metro.Inject
@@ -35,11 +34,9 @@ import io.element.android.libraries.matrix.api.permalink.PermalinkParser
 import io.element.android.libraries.matrix.api.timeline.item.event.AudioMessageType
 import io.element.android.libraries.matrix.api.timeline.item.event.EmoteMessageType
 import io.element.android.libraries.matrix.api.timeline.item.event.FileMessageType
-import io.element.android.libraries.matrix.api.timeline.item.event.FormattedBody
 import io.element.android.libraries.matrix.api.timeline.item.event.ImageMessageType
 import io.element.android.libraries.matrix.api.timeline.item.event.LocationMessageType
 import io.element.android.libraries.matrix.api.timeline.item.event.MessageContent
-import io.element.android.libraries.matrix.api.timeline.item.event.MessageFormat
 import io.element.android.libraries.matrix.api.timeline.item.event.NoticeMessageType
 import io.element.android.libraries.matrix.api.timeline.item.event.OtherMessageType
 import io.element.android.libraries.matrix.api.timeline.item.event.StickerMessageType
@@ -50,6 +47,7 @@ import io.element.android.libraries.matrix.ui.messages.toHtmlDocument
 import io.element.android.libraries.mediaviewer.api.util.FileExtensionExtractor
 import kotlinx.collections.immutable.persistentListOf
 import kotlinx.collections.immutable.toImmutableList
+import org.jsoup.nodes.Document
 import kotlin.time.Duration
 
 @Inject
@@ -60,7 +58,7 @@ class TimelineItemContentMessageFactory(
     private val permalinkParser: PermalinkParser,
     private val textPillificationHelper: TextPillificationHelper,
 ) {
-    suspend fun create(
+    fun create(
         content: MessageContent,
         senderDisambiguatedDisplayName: String,
         eventId: EventId?,
@@ -68,26 +66,29 @@ class TimelineItemContentMessageFactory(
         return when (val messageType = content.type) {
             is EmoteMessageType -> {
                 val emoteBody = "* $senderDisambiguatedDisplayName ${messageType.body.trimEnd()}"
-                val formattedBody = parseHtml(messageType.formatted, prefix = "* $senderDisambiguatedDisplayName") ?: textPillificationHelper.pillify(
-                    emoteBody
-                ).safeLinkify()
+                val dom = messageType.formatted?.toHtmlDocument(
+                    permalinkParser = permalinkParser,
+                    prefix = "* $senderDisambiguatedDisplayName",
+                )
+                val formattedBody = dom?.let(::parseHtml)
+                    ?: textPillificationHelper.pillify(emoteBody).safeLinkify()
                 TimelineItemEmoteContent(
                     body = emoteBody,
-                    htmlDocument = messageType.formatted?.toHtmlDocument(
-                        permalinkParser = permalinkParser,
-                        prefix = "* $senderDisambiguatedDisplayName",
-                    ),
+                    htmlDocument = dom,
                     formattedBody = formattedBody,
                     isEdited = content.isEdited,
                 )
             }
             is ImageMessageType -> {
+                val dom = messageType.formattedCaption?.toHtmlDocument(permalinkParser = permalinkParser)
+                val formattedCaption = dom?.let(::parseHtml)
+                    ?: messageType.caption?.withLinks()
                 val aspectRatio = aspectRatioOf(messageType.info?.width, messageType.info?.height)
                 TimelineItemImageContent(
                     filename = messageType.filename,
                     fileSize = messageType.info?.size ?: 0,
                     caption = messageType.caption?.trimEnd(),
-                    formattedCaption = parseHtml(messageType.formattedCaption) ?: messageType.caption?.withLinks(),
+                    formattedCaption = formattedCaption,
                     isEdited = content.isEdited,
                     mediaSource = messageType.source,
                     thumbnailSource = messageType.info?.thumbnailSource,
@@ -103,12 +104,15 @@ class TimelineItemContentMessageFactory(
                 )
             }
             is StickerMessageType -> {
+                val dom = messageType.formattedCaption?.toHtmlDocument(permalinkParser = permalinkParser)
+                val formattedCaption = dom?.let(::parseHtml)
+                    ?: messageType.caption?.withLinks()
                 val aspectRatio = aspectRatioOf(messageType.info?.width, messageType.info?.height)
                 TimelineItemStickerContent(
                     filename = messageType.filename,
                     fileSize = messageType.info?.size ?: 0,
                     caption = messageType.caption?.trimEnd(),
-                    formattedCaption = parseHtml(messageType.formattedCaption) ?: messageType.caption?.withLinks(),
+                    formattedCaption = formattedCaption,
                     isEdited = content.isEdited,
                     mediaSource = messageType.source,
                     thumbnailSource = messageType.info?.thumbnailSource,
@@ -140,12 +144,15 @@ class TimelineItemContentMessageFactory(
                 }
             }
             is VideoMessageType -> {
+                val dom = messageType.formattedCaption?.toHtmlDocument(permalinkParser = permalinkParser)
+                val formattedCaption = dom?.let(::parseHtml)
+                    ?: messageType.caption?.withLinks()
                 val aspectRatio = aspectRatioOf(messageType.info?.width, messageType.info?.height)
                 TimelineItemVideoContent(
                     filename = messageType.filename,
                     fileSize = messageType.info?.size ?: 0,
                     caption = messageType.caption?.trimEnd(),
-                    formattedCaption = parseHtml(messageType.formattedCaption) ?: messageType.caption?.withLinks(),
+                    formattedCaption = formattedCaption,
                     isEdited = content.isEdited,
                     thumbnailSource = messageType.info?.thumbnailSource,
                     mediaSource = messageType.source,
@@ -162,11 +169,14 @@ class TimelineItemContentMessageFactory(
                 )
             }
             is AudioMessageType -> {
+                val dom = messageType.formattedCaption?.toHtmlDocument(permalinkParser = permalinkParser)
+                val formattedCaption = dom?.let(::parseHtml)
+                    ?: messageType.caption?.withLinks()
                 TimelineItemAudioContent(
                     filename = messageType.filename,
                     fileSize = messageType.info?.size ?: 0,
                     caption = messageType.caption?.trimEnd(),
-                    formattedCaption = parseHtml(messageType.formattedCaption) ?: messageType.caption?.withLinks(),
+                    formattedCaption = formattedCaption,
                     isEdited = content.isEdited,
                     mediaSource = messageType.source,
                     duration = messageType.info?.duration ?: Duration.ZERO,
@@ -176,12 +186,15 @@ class TimelineItemContentMessageFactory(
                 )
             }
             is VoiceMessageType -> {
+                val dom = messageType.formattedCaption?.toHtmlDocument(permalinkParser = permalinkParser)
+                val formattedCaption = dom?.let(::parseHtml)
+                    ?: messageType.caption?.withLinks()
                 TimelineItemVoiceContent(
                     eventId = eventId,
                     filename = messageType.filename,
                     fileSize = messageType.info?.size ?: 0,
                     caption = messageType.caption?.trimEnd(),
-                    formattedCaption = parseHtml(messageType.formattedCaption) ?: messageType.caption?.withLinks(),
+                    formattedCaption = formattedCaption,
                     isEdited = content.isEdited,
                     mediaSource = messageType.source,
                     duration = messageType.info?.duration ?: Duration.ZERO,
@@ -192,12 +205,15 @@ class TimelineItemContentMessageFactory(
                 )
             }
             is FileMessageType -> {
+                val dom = messageType.formattedCaption?.toHtmlDocument(permalinkParser = permalinkParser)
+                val formattedCaption = dom?.let(::parseHtml)
+                    ?: messageType.caption?.withLinks()
                 val fileExtension = fileExtensionExtractor.extractFromName(messageType.filename)
                 TimelineItemFileContent(
                     filename = messageType.filename,
                     fileSize = messageType.info?.size ?: 0,
                     caption = messageType.caption?.trimEnd(),
-                    formattedCaption = parseHtml(messageType.formattedCaption) ?: messageType.caption?.withLinks(),
+                    formattedCaption = formattedCaption,
                     isEdited = content.isEdited,
                     thumbnailSource = messageType.info?.thumbnailSource,
                     mediaSource = messageType.source,
@@ -208,9 +224,9 @@ class TimelineItemContentMessageFactory(
             }
             is NoticeMessageType -> {
                 val body = messageType.body.trimEnd()
-                val formattedBody = parseHtml(messageType.formatted) ?: textPillificationHelper.pillify(
-                    body
-                ).safeLinkify()
+                val dom = messageType.formatted?.toHtmlDocument(permalinkParser = permalinkParser)
+                val formattedBody = dom?.let(::parseHtml)
+                    ?: textPillificationHelper.pillify(body).safeLinkify()
                 val htmlDocument = messageType.formatted?.toHtmlDocument(permalinkParser = permalinkParser)
                 TimelineItemNoticeContent(
                     body = body,
@@ -221,12 +237,13 @@ class TimelineItemContentMessageFactory(
             }
             is TextMessageType -> {
                 val body = messageType.body.trimEnd()
-                val formattedBody = parseHtml(messageType.formatted) ?: textPillificationHelper.pillify(
-                    body
-                ).safeLinkify()
+                val dom = messageType.formatted?.toHtmlDocument(permalinkParser = permalinkParser)
+                val formattedBody = dom?.let(::parseHtml)
+                    ?: textPillificationHelper.pillify(body).safeLinkify()
+                val htmlDocument = messageType.formatted?.toHtmlDocument(permalinkParser = permalinkParser)
                 TimelineItemTextContent(
                     body = body,
-                    htmlDocument = messageType.formatted?.toHtmlDocument(permalinkParser = permalinkParser),
+                    htmlDocument = htmlDocument,
                     formattedBody = formattedBody,
                     isEdited = content.isEdited,
                 )
@@ -253,21 +270,11 @@ class TimelineItemContentMessageFactory(
         return result?.takeIf { it.isFinite() }
     }
 
-    private fun parseHtml(formattedBody: FormattedBody?, prefix: String? = null): CharSequence? {
-        if (formattedBody == null || formattedBody.format != MessageFormat.HTML) return null
-        val result = htmlConverterProvider.provide()
-            .fromHtmlToSpans(formattedBody.body.trimEnd())
+    private fun parseHtml(document: Document): CharSequence? {
+        return htmlConverterProvider.provide()
+            .fromDocumentToSpans(document)
             .let { textPillificationHelper.pillify(it) }
             .safeLinkify()
-        return if (prefix != null) {
-            buildSpannedString {
-                append(prefix)
-                append(" ")
-                append(result)
-            }
-        } else {
-            result
-        }
     }
 }
 
diff --git a/features/messages/impl/src/test/kotlin/io/element/android/features/messages/impl/timeline/factories/event/TimelineItemContentMessageFactoryTest.kt b/features/messages/impl/src/test/kotlin/io/element/android/features/messages/impl/timeline/factories/event/TimelineItemContentMessageFactoryTest.kt
index 160e368916..9f23388ecb 100644
--- a/features/messages/impl/src/test/kotlin/io/element/android/features/messages/impl/timeline/factories/event/TimelineItemContentMessageFactoryTest.kt
+++ b/features/messages/impl/src/test/kotlin/io/element/android/features/messages/impl/timeline/factories/event/TimelineItemContentMessageFactoryTest.kt
@@ -67,6 +67,7 @@ import io.element.android.libraries.mediaviewer.test.util.FileExtensionExtractor
 import kotlinx.collections.immutable.persistentListOf
 import kotlinx.collections.immutable.toImmutableList
 import kotlinx.coroutines.test.runTest
+import org.jsoup.nodes.Document
 import org.junit.Assert.fail
 import org.junit.Test
 import org.junit.runner.RunWith
@@ -187,7 +188,7 @@ class TimelineItemContentMessageFactoryTest {
             }
         }.toSpannable()
         val sut = createTimelineItemContentMessageFactory(
-            htmlConverterTransform = { expected }
+            domConverterTransform = { expected }
         )
         val result = sut.create(
             content = createMessageContent(
@@ -679,7 +680,7 @@ class TimelineItemContentMessageFactoryTest {
             }
         }.toSpannable()
         val sut = createTimelineItemContentMessageFactory(
-            htmlConverterTransform = { expectedSpanned },
+            domConverterTransform = { expectedSpanned },
             permalinkParser = FakePermalinkParser { PermalinkData.FallbackLink(Uri.EMPTY) }
         )
         val result = sut.create(
@@ -765,11 +766,12 @@ class TimelineItemContentMessageFactoryTest {
 
     private fun createTimelineItemContentMessageFactory(
         htmlConverterTransform: (String) -> CharSequence = { it },
+        domConverterTransform: (Document) -> CharSequence = { it.body().html() },
         permalinkParser: FakePermalinkParser = FakePermalinkParser(),
     ) = TimelineItemContentMessageFactory(
         fileSizeFormatter = FakeFileSizeFormatter(),
         fileExtensionExtractor = FileExtensionExtractorWithoutValidation(),
-        htmlConverterProvider = FakeHtmlConverterProvider(htmlConverterTransform),
+        htmlConverterProvider = FakeHtmlConverterProvider(htmlConverterTransform, domConverterTransform),
         permalinkParser = permalinkParser,
         textPillificationHelper = FakeTextPillificationHelper(),
     )
diff --git a/features/messages/test/src/main/kotlin/io/element/android/features/messages/test/timeline/FakeHtmlConverterProvider.kt b/features/messages/test/src/main/kotlin/io/element/android/features/messages/test/timeline/FakeHtmlConverterProvider.kt
index 75b700b58d..1277783f6a 100644
--- a/features/messages/test/src/main/kotlin/io/element/android/features/messages/test/timeline/FakeHtmlConverterProvider.kt
+++ b/features/messages/test/src/main/kotlin/io/element/android/features/messages/test/timeline/FakeHtmlConverterProvider.kt
@@ -11,9 +11,11 @@ package io.element.android.features.messages.test.timeline
 import androidx.compose.runtime.Composable
 import io.element.android.features.messages.api.timeline.HtmlConverterProvider
 import io.element.android.wysiwyg.utils.HtmlConverter
+import org.jsoup.nodes.Document
 
 class FakeHtmlConverterProvider(
     private val transform: (String) -> CharSequence = { it },
+    private val transformDom: (Document) -> CharSequence = { it.html() },
 ) : HtmlConverterProvider {
     @Composable
     override fun Update() = Unit
@@ -23,6 +25,10 @@ class FakeHtmlConverterProvider(
             override fun fromHtmlToSpans(html: String): CharSequence {
                 return transform(html)
             }
+
+            override fun fromDocumentToSpans(dom: Document): CharSequence {
+                return transformDom(dom)
+            }
         }
     }
 }
diff --git a/gradle/libs.versions.toml b/gradle/libs.versions.toml
index 424f7a5620..ffabfc9446 100644
--- a/gradle/libs.versions.toml
+++ b/gradle/libs.versions.toml
@@ -44,7 +44,7 @@ coil = "3.3.0"
 showkase = "1.0.5"
 appyx = "1.7.1"
 sqldelight = "2.2.1"
-wysiwyg = "2.40.0"
+wysiwyg = "2.41.0"
 telephoto = "0.18.0"
 haze = "1.7.1"
 
diff --git a/libraries/matrixui/build.gradle.kts b/libraries/matrixui/build.gradle.kts
index 94aa388c0c..5513dc240e 100644
--- a/libraries/matrixui/build.gradle.kts
+++ b/libraries/matrixui/build.gradle.kts
@@ -36,7 +36,7 @@ dependencies {
     implementation(projects.libraries.uiStrings)
     implementation(projects.libraries.testtags)
     implementation(libs.coil.compose)
-    implementation(libs.jsoup)
+    implementation(libs.matrix.richtexteditor)
     implementation(projects.libraries.previewutils)
 
     testCommonDependencies(libs, true)
diff --git a/libraries/matrixui/src/main/kotlin/io/element/android/libraries/matrix/ui/messages/ToHtmlDocument.kt b/libraries/matrixui/src/main/kotlin/io/element/android/libraries/matrix/ui/messages/ToHtmlDocument.kt
index 5a2297ec1f..ee9de51681 100644
--- a/libraries/matrixui/src/main/kotlin/io/element/android/libraries/matrix/ui/messages/ToHtmlDocument.kt
+++ b/libraries/matrixui/src/main/kotlin/io/element/android/libraries/matrix/ui/messages/ToHtmlDocument.kt
@@ -12,7 +12,7 @@ import io.element.android.libraries.matrix.api.permalink.PermalinkData
 import io.element.android.libraries.matrix.api.permalink.PermalinkParser
 import io.element.android.libraries.matrix.api.timeline.item.event.FormattedBody
 import io.element.android.libraries.matrix.api.timeline.item.event.MessageFormat
-import org.jsoup.Jsoup
+import io.element.android.wysiwyg.utils.HtmlToDomParser
 import org.jsoup.nodes.Document
 
 /**
@@ -34,9 +34,9 @@ fun FormattedBody.toHtmlDocument(
         ?.trimEnd()
         ?.let { formattedBody ->
             val dom = if (prefix != null) {
-                Jsoup.parse("$prefix $formattedBody")
+                HtmlToDomParser.document("$prefix $formattedBody")
             } else {
-                Jsoup.parse(formattedBody)
+                HtmlToDomParser.document(formattedBody)
             }
 
             // Prepend `@` to mentions
diff --git a/libraries/matrixui/src/main/kotlin/io/element/android/libraries/matrix/ui/messages/ToPlainText.kt b/libraries/matrixui/src/main/kotlin/io/element/android/libraries/matrix/ui/messages/ToPlainText.kt
index 2fc371c71b..d58d12b785 100644
--- a/libraries/matrixui/src/main/kotlin/io/element/android/libraries/matrix/ui/messages/ToPlainText.kt
+++ b/libraries/matrixui/src/main/kotlin/io/element/android/libraries/matrix/ui/messages/ToPlainText.kt
@@ -55,8 +55,15 @@ private class PlainTextNodeVisitor : NodeVisitor {
     private val builder = StringBuilder()
 
     override fun head(node: Node, depth: Int) {
-        if (node is TextNode && node.text().isNotBlank()) {
-            builder.append(node.text())
+        if (node is TextNode) {
+            // If the text node is blank, only add a single whitespace char if there wasn't already one
+            if (node.text().isBlank()) {
+                if (builder.lastOrNull()?.isWhitespace() == false) {
+                    builder.append(" ")
+                }
+            } else {
+                builder.append(node.text())
+            }
         } else if (node is Element && node.tagName() == "li") {
             val index = node.elementSiblingIndex() + 1
             val isOrdered = node.parent()?.nodeName()?.lowercase() == "ol"
diff --git a/libraries/matrixui/src/test/kotlin/io/element/android/libraries/matrix/ui/messages/ToPlainTextTest.kt b/libraries/matrixui/src/test/kotlin/io/element/android/libraries/matrix/ui/messages/ToPlainTextTest.kt
index 5345113dc2..607f825401 100644
--- a/libraries/matrixui/src/test/kotlin/io/element/android/libraries/matrix/ui/messages/ToPlainTextTest.kt
+++ b/libraries/matrixui/src/test/kotlin/io/element/android/libraries/matrix/ui/messages/ToPlainTextTest.kt
@@ -45,7 +45,7 @@ class ToPlainTextTest {
         val formattedBody = FormattedBody(
             format = MessageFormat.HTML,
             body = """
-                Hello world
+                Hello <strong>formatted</strong> <em>world</em>
                 <ul><li>This is an unordered list.</li></ul>
                 <ol><li>This is an ordered list.</li></ol>
                 <br />
@@ -53,7 +53,7 @@ class ToPlainTextTest {
         )
         assertThat(formattedBody.toPlainText(permalinkParser = FakePermalinkParser())).isEqualTo(
             """
-            Hello world 
+            Hello formatted world 
             • This is an unordered list.
             1. This is an ordered list.
             """.trimIndent()