diff --git a/matrix/services/sync/src/main/kotlin/app/dapk/st/matrix/sync/internal/sync/message/AccumulatingRichTextContentParser.kt b/matrix/services/sync/src/main/kotlin/app/dapk/st/matrix/sync/internal/sync/message/AccumulatingRichTextContentParser.kt
new file mode 100644
index 0000000..17afd8f
--- /dev/null
+++ b/matrix/services/sync/src/main/kotlin/app/dapk/st/matrix/sync/internal/sync/message/AccumulatingRichTextContentParser.kt
@@ -0,0 +1,85 @@
+package app.dapk.st.matrix.sync.internal.sync.message
+
+import app.dapk.st.matrix.sync.internal.sync.message.html.HtmlProcessor
+import app.dapk.st.matrix.sync.internal.sync.message.url.UrlParser
+
+private const val MAX_NESTING_LIMIT = 20
+
+class AccumulatingRichTextContentParser : AccumulatingContentParser {
+
+    private val urlParser = UrlParser()
+    private val tagProcessor = HtmlProcessor()
+
+    override fun parse(input: String, accumulator: ContentAccumulator, nestingLevel: Int): ContentAccumulator {
+        if (nestingLevel >= MAX_NESTING_LIMIT) {
+            accumulator.appendText(input)
+        } else {
+            iterate { index ->
+                process(
+                    input,
+                    index,
+                    processTag = {
+                        prependTextBeforeCapture(input, index, it, accumulator)
+                        tagProcessor.process(input, it, accumulator, nestingLevel, nestedParser = this)
+                    },
+                    processUrl = {
+                        prependTextBeforeCapture(input, index, it, accumulator)
+                        urlParser.parseUrl(input, it, accumulator)
+                    }
+                ).also {
+                    if (it == -1) {
+                        appendRemainingText(index, input, accumulator)
+                    }
+                }
+            }
+        }
+        return accumulator
+    }
+
+    private inline fun iterate(action: (Int) -> Int) {
+        var result = 0
+        while (result != -1) {
+            result = action(result)
+        }
+    }
+
+    private fun process(input: String, searchIndex: Int, processTag: (Int) -> Int, processUrl: (Int) -> Int): Int {
+        val tagOpen = input.indexOf('<', startIndex = searchIndex)
+        val httpOpen = input.indexOf("http", startIndex = searchIndex)
+        return selectProcessor(
+            tagOpen,
+            httpOpen,
+            processTag = { processTag(tagOpen) },
+            processUrl = { processUrl(httpOpen) }
+        )
+    }
+
+    private inline fun selectProcessor(tagOpen: Int, httpOpen: Int, processTag: () -> Int, processUrl: () -> Int) = when {
+        tagOpen == -1 && httpOpen == -1 -> -1
+        tagOpen != -1 && httpOpen == -1 -> processTag()
+        tagOpen == -1 && httpOpen != -1 -> processUrl()
+        tagOpen == httpOpen -> {
+            // favour tags as urls can existing within tags
+            processTag()
+        }
+
+        else -> {
+            when (tagOpen < httpOpen) {
+                true -> processTag()
+                false -> processUrl()
+            }
+        }
+    }
+
+    private fun prependTextBeforeCapture(input: String, index: Int, captureIndex: Int, accumulator: ContentAccumulator) {
+        if (index < captureIndex) {
+            accumulator.appendText(input.substring(index, captureIndex))
+        }
+    }
+
+    private fun appendRemainingText(index: Int, input: String, accumulator: ContentAccumulator) {
+        if (index < input.length) {
+            accumulator.appendText(input.substring(index, input.length))
+        }
+    }
+}
diff --git a/matrix/services/sync/src/main/kotlin/app/dapk/st/matrix/sync/internal/sync/message/HtmlParser.kt b/matrix/services/sync/src/main/kotlin/app/dapk/st/matrix/sync/internal/sync/message/HtmlParser.kt
deleted file mode 100644
index e43ab24..0000000
--- a/matrix/services/sync/src/main/kotlin/app/dapk/st/matrix/sync/internal/sync/message/HtmlParser.kt
+++ /dev/null
@@ -1,248 +0,0 @@
-package app.dapk.st.matrix.sync.internal.sync.message
-
-import app.dapk.st.matrix.common.UserId
-
-private const val TAG_OPEN = '<'
-private const val TAG_CLOSE = '>'
-private const val NO_RESULT_FOUND = -1
-private val SKIPPED_TAGS = setOf("mx-reply")
-
-internal class HtmlParser {
-
-    fun test(startingFrom: Int, input: String) = input.indexOf(TAG_OPEN, startingFrom)
-
-    fun parseHtmlTags(input: String, searchIndex: Int, builder: PartBuilder, nestingLevel: Int = 0): SearchIndex = input.findTag(
-        fromIndex = searchIndex,
-        onInvalidTag = { builder.appendText(input[it].toString()) },
-        onTag = { tagOpen, tagClose ->
-            val (wholeTag, tagName) = parseTag(input, tagOpen, tagClose)
-
-            when {
-                tagName.startsWith('@') -> {
-                    appendTextBeforeTag(searchIndex, tagOpen, builder, input)
-                    builder.appendPerson(UserId(tagName), tagName)
-                    tagClose.next()
-                }
-
-                tagName == "br" -> {
-                    appendTextBeforeTag(searchIndex, tagOpen, builder, input)
-                    builder.appendNewline()
-                    tagClose.next()
-                }
-
-                else -> parseTagWithContent(input, tagName, tagClose, searchIndex, tagOpen, wholeTag, builder, nestingLevel)
-            }
-        }
-    )
-
-    private fun parseTagWithContent(
-        input: String,
-        tagName: String,
-        tagClose: Int,
-        searchIndex: Int,
-        tagOpen: Int,
-        wholeTag: String,
-        builder: PartBuilder,
-        nestingLevel: Int
-    ): Int {
-        val exitTag = "</$tagName>"
-        val exitIndex = input.indexOf(exitTag, startIndex = tagClose)
-        val exitTagCloseIndex = exitIndex + exitTag.length
-        return when {
-            exitIndex == NO_RESULT_FOUND -> {
-                builder.appendText(input[searchIndex].toString())
-                searchIndex.next()
-            }
-
-            SKIPPED_TAGS.contains(tagName) -> exitTagCloseIndex
-
-            else -> {
-                appendTextBeforeTag(searchIndex, tagOpen, builder, input)
-                val tagContent = input.substring(tagClose + 1, exitIndex)
-                handleTagWithContent(input, tagName, wholeTag, builder, tagContent, exitTagCloseIndex, nestingLevel)
-            }
-        }
-    }
-
-    private fun handleTagWithContent(
-        input: String,
-        tagName: String,
-        wholeTag: String,
-        builder: PartBuilder,
-        tagContent: String,
-        exitTagCloseIndex: Int,
-        nestingLevel: Int,
-    ) = when (tagName) {
-        "a" -> {
-            val findHrefUrl = wholeTag.findTagAttribute("href")
-            when {
-                findHrefUrl == null -> {
-                    builder.appendText(tagContent)
-                    exitTagCloseIndex
-                }
-
-                findHrefUrl.startsWith("https://matrix.to/#/@") -> {
-                    val userId = UserId(findHrefUrl.substringAfter("https://matrix.to/#/").substringBeforeLast("\""))
-                    builder.appendPerson(userId, "@${tagContent.removePrefix("@")}")
-                    ignoreMatrixColonMentionSuffix(input, exitTagCloseIndex)
-                }
-
-                else -> {
-                    builder.appendLink(findHrefUrl, label = tagContent)
-                    exitTagCloseIndex
-                }
-            }
-        }
-
-        "b", "strong" -> {
-            builder.appendBold(tagContent)
-            exitTagCloseIndex
-        }
-
-        "blockquote" -> {
-            if (tagContent.isNotEmpty() && nestingLevel < 3) {
-                var lastIndex = 0
-                val trimmedTagContent = tagContent.trim()
-                builder.appendText("> ")
-                iterateSearchIndex { searchIndex ->
-                    lastIndex = searchIndex
-                    parseHtmlTags(trimmedTagContent, searchIndex, builder, nestingLevel = nestingLevel + 1)
-                }
-
-                if (lastIndex < trimmedTagContent.length) {
-                    builder.appendText(trimmedTagContent.substring(lastIndex))
-                }
-            }
-
-            builder.appendNewline()
-            exitTagCloseIndex
-        }
-
-        "p" -> {
-            if (tagContent.isNotEmpty() && nestingLevel < 2) {
-                var lastIndex = 0
-                iterateSearchIndex { searchIndex ->
-                    lastIndex = searchIndex
-                    parseHtmlTags(tagContent, searchIndex, builder, nestingLevel = nestingLevel + 1)
-                }
-
-                if (lastIndex < tagContent.length) {
-                    builder.appendText(tagContent.substring(lastIndex))
-                }
-            }
-
-            builder.appendNewline()
-            exitTagCloseIndex
-        }
-
-        "ul", "ol" -> {
-            parseList(tagName, tagContent, builder)
-            exitTagCloseIndex
-        }
-
-        "h1", "h2", "h3", "h4", "h5" -> {
-            builder.appendBold(tagContent.trim())
-            builder.appendNewline()
-            exitTagCloseIndex
-        }
-
-        "i", "em" -> {
-            builder.appendItalic(tagContent)
-            exitTagCloseIndex
-        }
-
-        else -> {
-            builder.appendText(tagContent)
-            exitTagCloseIndex
-        }
-    }
-
-    private fun ignoreMatrixColonMentionSuffix(input: String, exitTagCloseIndex: Int) = if (input.getOrNull(exitTagCloseIndex) == ':') {
-        exitTagCloseIndex.next()
-    } else {
-        exitTagCloseIndex
-    }
-
-    private fun appendTextBeforeTag(searchIndex: Int, tagOpen: Int, builder: PartBuilder, input: String) {
-        if (searchIndex != tagOpen) {
-            builder.appendText(input.substring(searchIndex, tagOpen))
-        }
-    }
-
-    private fun String.findTag(fromIndex: Int, onInvalidTag: (Int) -> Unit, onTag: (Int, Int) -> Int): Int {
-        return when (val foundIndex = this.indexOf(TAG_OPEN, startIndex = fromIndex)) {
-            NO_RESULT_FOUND -> END_SEARCH
-
-            else -> when (val closeIndex = indexOf(TAG_CLOSE, startIndex = foundIndex)) {
-                NO_RESULT_FOUND -> {
-                    onInvalidTag(fromIndex)
-                    fromIndex + 1
-                }
-
-                else -> onTag(foundIndex, closeIndex)
-            }
-        }
-    }
-
-    private fun parseList(parentTag: String, parentContent: String, builder: PartBuilder) {
-        var listIndex = 1
-        iterateSearchIndex { nextIndex ->
-            singleTagParser(parentContent, "li", nextIndex, builder) { wholeTag, tagContent ->
-                val content = when (parentTag) {
-                    "ol" -> {
-                        listIndex = wholeTag.findTagAttribute("value")?.toInt() ?: listIndex
-                        "$listIndex. $tagContent".also { listIndex++ }
-                    }
-
-                    else -> "- $tagContent"
-                }
-                builder.appendText(content)
-                builder.appendNewline()
-            }
-        }
-    }
-
-    private fun singleTagParser(content: String, wantedTagName: String, searchIndex: Int, builder: PartBuilder, onTag: (String, String) -> Unit): SearchIndex {
-        return content.findTag(
-            fromIndex = searchIndex,
-            onInvalidTag = { builder.appendText(content[it].toString()) },
-            onTag = { tagOpen, tagClose ->
-                val (wholeTag, tagName) = parseTag(content, tagOpen, tagClose)
-
-                if (tagName == wantedTagName) {
-                    val exitTag = "</$tagName>"
-                    val exitIndex = content.indexOf(exitTag, startIndex = tagClose)
-                    val exitTagCloseIndex = exitIndex + exitTag.length
-                    if (exitIndex == END_SEARCH) {
-                        builder.appendText(content[searchIndex].toString())
-                        searchIndex.next()
-                    } else {
-                        val tagContent = content.substring(tagClose + 1, exitIndex)
-                        onTag(wholeTag, tagContent)
-                        exitTagCloseIndex
-                    }
-                } else {
-                    END_SEARCH
-                }
-            }
-        )
-    }
-
-    private fun parseTag(input: String, tagOpen: Int, tagClose: Int): Pair<String, String> {
-        val wholeTag = input.substring(tagOpen, tagClose + 1)
-        val tagName = wholeTag.substring(1, wholeTag.indexOfFirst { it == '>' || it == ' ' })
-        return wholeTag to tagName
-    }
-}
-
-private fun String.findTagAttribute(name: String): String? {
-    val attribute = "$name="
-    return this.indexOf(attribute).let {
-        if (it == NO_RESULT_FOUND) {
-            null
-        } else {
-            val start = it + attribute.length
-            this.substring(start).substringAfter('\"').substringBefore('\"')
-        }
-    }
-}
diff --git a/matrix/services/sync/src/main/kotlin/app/dapk/st/matrix/sync/internal/sync/message/ParserScope.kt b/matrix/services/sync/src/main/kotlin/app/dapk/st/matrix/sync/internal/sync/message/ParserScope.kt
deleted file mode 100644
index 8674f47..0000000
--- a/matrix/services/sync/src/main/kotlin/app/dapk/st/matrix/sync/internal/sync/message/ParserScope.kt
+++ /dev/null
@@ -1,13 +0,0 @@
-package app.dapk.st.matrix.sync.internal.sync.message
-
-internal typealias SearchIndex = Int
-
-internal fun Int.next() = this + 1
-
-
-internal interface ParserScope {
-    fun appendTextBeforeTag(searchIndex: Int, tagOpen: Int, builder: PartBuilder, input: String)
-
-    fun SearchIndex.next(): SearchIndex
-
-}
\ No newline at end of file
diff --git a/matrix/services/sync/src/main/kotlin/app/dapk/st/matrix/sync/internal/sync/message/RichMessageParser.kt b/matrix/services/sync/src/main/kotlin/app/dapk/st/matrix/sync/internal/sync/message/RichMessageParser.kt
deleted file mode 100644
index 97960b2..0000000
--- a/matrix/services/sync/src/main/kotlin/app/dapk/st/matrix/sync/internal/sync/message/RichMessageParser.kt
+++ /dev/null
@@ -1,71 +0,0 @@
-package app.dapk.st.matrix.sync.internal.sync.message
-
-import app.dapk.st.matrix.common.RichText
-import kotlin.math.max
-
-internal const val END_SEARCH = -1
-
-class RichMessageParser {
-
-    private val htmlParser = HtmlParser()
-    private val urlParser = UrlParser()
-
-    fun parse(source: String): RichText {
-        val input = source
-            .removeHtmlEntities()
-            .dropTextFallback()
-        return RichText(collectRichText(input).build())
-    }
-
-    private fun collectRichText(input: String) = PartBuilder().also { builder ->
-        iterateSearchIndex { nextIndex ->
-            val htmlStart = htmlParser.test(nextIndex, input)
-            val urlStart = urlParser.test(nextIndex, input)
-
-            val firstResult = if (htmlStart < urlStart) {
-                htmlParser.parseHtmlTags(input, nextIndex, builder)
-            } else {
-                urlParser.parseUrl(input, nextIndex, builder)
-            }
-
-            val secondStartIndex = findUrlStartIndex(firstResult, nextIndex)
-            val secondResult = if (htmlStart < urlStart) {
-                urlParser.parseUrl(input, secondStartIndex, builder)
-            } else {
-                htmlParser.parseHtmlTags(input, secondStartIndex, builder)
-            }
-
-            val hasReachedEnd = hasReachedEnd(firstResult, secondResult, input)
-            if (hasReachedEnd && hasUnprocessedText(firstResult, secondResult, input)) {
-                builder.appendText(input.substring(nextIndex))
-            }
-            if (hasReachedEnd) END_SEARCH else max(firstResult, secondResult)
-        }
-    }
-
-    private fun hasUnprocessedText(htmlResult: Int, urlResult: Int, input: String) = htmlResult < input.length && urlResult < input.length
-
-    private fun findUrlStartIndex(htmlResult: Int, searchIndex: Int) = when {
-        htmlResult == END_SEARCH && searchIndex == 0 -> 0
-        htmlResult == END_SEARCH -> searchIndex
-        else -> htmlResult
-    }
-
-    private fun hasReachedEnd(htmlResult: SearchIndex, urlResult: Int, input: String) =
-        (htmlResult == END_SEARCH && urlResult == END_SEARCH) || (htmlResult >= input.length || urlResult >= input.length)
-
-}
-
-private fun String.removeHtmlEntities() = this.replace("&quot;", "\"").replace("&#39;", "'").replace("&apos;", "'").replace("&amp;", "&")
-
-private fun String.dropTextFallback() = this.lines()
-    .dropWhile { it.startsWith("> ") || it.isEmpty() }
-    .joinToString(separator = "\n")
-
-internal fun iterateSearchIndex(action: (SearchIndex) -> SearchIndex): SearchIndex {
-    var nextIndex = 0
-    while (nextIndex != END_SEARCH) {
-        nextIndex = action(nextIndex)
-    }
-    return nextIndex
-}
\ No newline at end of file
diff --git a/matrix/services/sync/src/main/kotlin/app/dapk/st/matrix/sync/internal/sync/message/RichTextMessageParser.kt b/matrix/services/sync/src/main/kotlin/app/dapk/st/matrix/sync/internal/sync/message/RichTextMessageParser.kt
new file mode 100644
index 0000000..45719e3
--- /dev/null
+++ b/matrix/services/sync/src/main/kotlin/app/dapk/st/matrix/sync/internal/sync/message/RichTextMessageParser.kt
@@ -0,0 +1,34 @@
+package app.dapk.st.matrix.sync.internal.sync.message
+
+import app.dapk.st.matrix.common.RichText
+
+fun interface NestedParser {
+    fun parse(content: String, accumulator: ContentAccumulator)
+}
+
+fun interface TagParser {
+    fun parse(tagName: String, attributes: Map<String, String>, content: String, accumulator: ContentAccumulator, parser: NestedParser)
+}
+
+fun interface AccumulatingContentParser {
+    fun parse(input: String, accumulator: ContentAccumulator, nestingLevel: Int): ContentAccumulator
+}
+
+class RichMessageParser(
+    private val accumulatingParser: AccumulatingContentParser = AccumulatingRichTextContentParser()
+) {
+
+    fun parse(source: String): RichText {
+        val input = source
+            .removeHtmlEntities()
+            .dropTextFallback()
+        return RichText(accumulatingParser.parse(input, RichTextPartBuilder(), nestingLevel = 0).build())
+    }
+
+}
+
+private fun String.removeHtmlEntities() = this.replace("&quot;", "\"").replace("&#39;", "'").replace("&apos;", "'").replace("&amp;", "&")
+
+private fun String.dropTextFallback() = this.lines()
+    .dropWhile { it.startsWith("> ") || it.isEmpty() }
+    .joinToString(separator = "\n")
diff --git a/matrix/services/sync/src/main/kotlin/app/dapk/st/matrix/sync/internal/sync/message/PartBuilder.kt b/matrix/services/sync/src/main/kotlin/app/dapk/st/matrix/sync/internal/sync/message/RichTextPartBuilder.kt
similarity index 67%
rename from matrix/services/sync/src/main/kotlin/app/dapk/st/matrix/sync/internal/sync/message/PartBuilder.kt
rename to matrix/services/sync/src/main/kotlin/app/dapk/st/matrix/sync/internal/sync/message/RichTextPartBuilder.kt
index e71a548..c7499e5 100644
--- a/matrix/services/sync/src/main/kotlin/app/dapk/st/matrix/sync/internal/sync/message/PartBuilder.kt
+++ b/matrix/services/sync/src/main/kotlin/app/dapk/st/matrix/sync/internal/sync/message/RichTextPartBuilder.kt
@@ -3,41 +3,50 @@ package app.dapk.st.matrix.sync.internal.sync.message
 import app.dapk.st.matrix.common.RichText
 import app.dapk.st.matrix.common.UserId
 
-internal class PartBuilder {
+interface ContentAccumulator {
+    fun appendText(value: String)
+    fun appendItalic(value: String)
+    fun appendBold(value: String)
+    fun appendPerson(userId: UserId, displayName: String)
+    fun appendLink(url: String, label: String?)
+    fun build(): List<RichText.Part>
+}
+
+class RichTextPartBuilder : ContentAccumulator {
 
     private var normalBuffer = StringBuilder()
 
     private val parts = mutableListOf<RichText.Part>()
 
-    fun appendText(value: String) {
+    override fun appendText(value: String) {
         normalBuffer.append(value.cleanFirstTextLine())
     }
 
-    fun appendItalic(value: String) {
+    override fun appendItalic(value: String) {
         flushNormalBuffer()
         parts.add(RichText.Part.Italic(value.cleanFirstTextLine()))
     }
 
-    fun appendBold(value: String) {
+    override fun appendBold(value: String) {
         flushNormalBuffer()
         parts.add(RichText.Part.Bold(value.cleanFirstTextLine()))
     }
 
     private fun String.cleanFirstTextLine() = if (parts.isEmpty() && normalBuffer.isEmpty()) this.trimStart() else this
 
-    fun appendPerson(userId: UserId, displayName: String) {
+    override fun appendPerson(userId: UserId, displayName: String) {
         flushNormalBuffer()
         parts.add(RichText.Part.Person(userId, displayName))
     }
 
-    fun appendLink(url: String, label: String?) {
+    override fun appendLink(url: String, label: String?) {
         flushNormalBuffer()
         parts.add(RichText.Part.Link(url, label ?: url))
     }
 
-    fun build(): List<RichText.Part> {
+    override fun build(): List<RichText.Part> {
         flushNormalBuffer()
-        return when(parts.isEmpty()) {
+        return when (parts.isEmpty()) {
             true -> parts
             else -> {
                 val last = parts.last()
@@ -59,16 +68,9 @@ internal class PartBuilder {
             normalBuffer.clear()
         }
     }
-
 }
 
-internal fun PartBuilder.appendTextBeforeTag(previousIndex: Int, tagOpenIndex: Int, input: String) {
-    if (previousIndex != tagOpenIndex) {
-        this.appendText(input.substring(previousIndex, tagOpenIndex))
-    }
-}
-
-internal fun PartBuilder.appendNewline() {
+internal fun ContentAccumulator.appendNewline() {
     this.appendText("\n")
 }
 
diff --git a/matrix/services/sync/src/main/kotlin/app/dapk/st/matrix/sync/internal/sync/message/html/HtmlProcessor.kt b/matrix/services/sync/src/main/kotlin/app/dapk/st/matrix/sync/internal/sync/message/html/HtmlProcessor.kt
new file mode 100644
index 0000000..98856d1
--- /dev/null
+++ b/matrix/services/sync/src/main/kotlin/app/dapk/st/matrix/sync/internal/sync/message/html/HtmlProcessor.kt
@@ -0,0 +1,27 @@
+package app.dapk.st.matrix.sync.internal.sync.message.html
+
+import app.dapk.st.matrix.sync.internal.sync.message.AccumulatingContentParser
+import app.dapk.st.matrix.sync.internal.sync.message.ContentAccumulator
+
+class HtmlProcessor {
+
+    private val tagCaptor = TagCaptor()
+    private val htmlTagParser = RichTextHtmlTagParser()
+
+    fun process(input: String, tagOpen: Int, partBuilder: ContentAccumulator, nestingLevel: Int, nestedParser: AccumulatingContentParser): Int {
+        val afterTagCaptureIndex = tagCaptor.tagCapture(input, tagOpen) { tagName, attributes, tagContent ->
+            htmlTagParser.parse(tagName, attributes, tagContent, partBuilder) { nestedContent, accumulator ->
+                nestedParser.parse(nestedContent, accumulator, nestingLevel + 1)
+            }
+        }
+        return when (afterTagCaptureIndex) {
+            -1 -> {
+                partBuilder.appendText(input[tagOpen].toString())
+                tagOpen + 1
+            }
+
+            else -> afterTagCaptureIndex
+        }
+    }
+
+}
\ No newline at end of file
diff --git a/matrix/services/sync/src/main/kotlin/app/dapk/st/matrix/sync/internal/sync/message/html/ListAccumulator.kt b/matrix/services/sync/src/main/kotlin/app/dapk/st/matrix/sync/internal/sync/message/html/ListAccumulator.kt
new file mode 100644
index 0000000..4d6dbc1
--- /dev/null
+++ b/matrix/services/sync/src/main/kotlin/app/dapk/st/matrix/sync/internal/sync/message/html/ListAccumulator.kt
@@ -0,0 +1,23 @@
+package app.dapk.st.matrix.sync.internal.sync.message.html
+
+import app.dapk.st.matrix.sync.internal.sync.message.ContentAccumulator
+
+internal interface ListAccumulator {
+    fun appendLinePrefix(index: Int?)
+}
+
+internal class OrderedListAccumulator(delegate: ContentAccumulator) : ContentAccumulator by delegate, ListAccumulator {
+
+    private var currentIndex = 1
+
+    override fun appendLinePrefix(index: Int?) {
+        currentIndex = index ?: currentIndex
+        appendText("$currentIndex. ")
+        currentIndex++
+    }
+}
+
+internal class UnorderedListAccumulator(delegate: ContentAccumulator) : ContentAccumulator by delegate, ListAccumulator {
+    override fun appendLinePrefix(index: Int?) = appendText("- ")
+}
+
diff --git a/matrix/services/sync/src/main/kotlin/app/dapk/st/matrix/sync/internal/sync/message/html/RichTextHtmlTagParser.kt b/matrix/services/sync/src/main/kotlin/app/dapk/st/matrix/sync/internal/sync/message/html/RichTextHtmlTagParser.kt
new file mode 100644
index 0000000..a3e3366
--- /dev/null
+++ b/matrix/services/sync/src/main/kotlin/app/dapk/st/matrix/sync/internal/sync/message/html/RichTextHtmlTagParser.kt
@@ -0,0 +1,95 @@
+package app.dapk.st.matrix.sync.internal.sync.message.html
+
+import app.dapk.st.matrix.common.UserId
+import app.dapk.st.matrix.sync.internal.sync.message.*
+
+class RichTextHtmlTagParser : TagParser {
+
+    override fun parse(
+        tagName: String,
+        attributes: Map<String, String>,
+        content: String,
+        accumulator: ContentAccumulator,
+        parser: NestedParser
+    ) {
+        when {
+            tagName.startsWith('@') -> {
+                accumulator.appendPerson(UserId(tagName), tagName)
+            }
+
+            else -> when (tagName) {
+                "br" -> {
+                    accumulator.appendNewline()
+                }
+
+                "a" -> {
+                    attributes["href"]?.let { url ->
+                        when {
+                            url.startsWith("https://matrix.to/#/@") -> {
+                                val userId = UserId(url.substringAfter("https://matrix.to/#/").substringBeforeLast("\""))
+                                accumulator.appendPerson(userId, "@${content.removePrefix("@")}")
+                            }
+
+                            else -> accumulator.appendLink(url, content)
+
+                        }
+                    } ?: accumulator.appendText(content)
+                }
+
+                "p" -> {
+                    parser.parse(content.trim(), accumulator)
+                    accumulator.appendNewline()
+                }
+
+                "blockquote" -> {
+                    accumulator.appendText("> ")
+                    parser.parse(content.trim(), accumulator)
+                }
+
+                "strong", "b" -> {
+                    accumulator.appendBold(content)
+                }
+
+                "em", "i" -> {
+                    accumulator.appendItalic(content)
+                }
+
+                "h1", "h2", "h3", "h4", "h5" -> {
+                    accumulator.appendBold(content)
+                    accumulator.appendNewline()
+                }
+
+                "ul", "ol" -> {
+                    when (tagName) {
+                        "ol" -> parser.parse(content, OrderedListAccumulator(accumulator))
+                        "ul" -> parser.parse(content, UnorderedListAccumulator(accumulator))
+                    }
+                }
+
+                "li" -> {
+                    (accumulator as ListAccumulator).appendLinePrefix(attributes["value"]?.toInt())
+
+                    val nestedList = when {
+                        content.contains("<ul>") -> "<ul>"
+                        content.contains("<ol>") -> "<ol>"
+                        else -> null
+                    }
+
+                    if (nestedList == null) {
+                        parser.parse(content.trim(), accumulator)
+                        accumulator.appendNewline()
+                    } else {
+                        val firstItemInNested = content.substringBefore(nestedList)
+                        parser.parse(firstItemInNested.trim(), accumulator)
+                        accumulator.appendNewline()
+                        parser.parse(content.substring(content.indexOf(nestedList)).trim(), accumulator)
+                    }
+                }
+
+                else -> {
+                    // skip tag
+                }
+            }
+        }
+    }
+}
\ No newline at end of file
diff --git a/matrix/services/sync/src/main/kotlin/app/dapk/st/matrix/sync/internal/sync/message/html/TagCaptor.kt b/matrix/services/sync/src/main/kotlin/app/dapk/st/matrix/sync/internal/sync/message/html/TagCaptor.kt
new file mode 100644
index 0000000..37b756a
--- /dev/null
+++ b/matrix/services/sync/src/main/kotlin/app/dapk/st/matrix/sync/internal/sync/message/html/TagCaptor.kt
@@ -0,0 +1,78 @@
+package app.dapk.st.matrix.sync.internal.sync.message.html
+
+class TagCaptor {
+
+    fun tagCapture(input: String, startIndex: Int, tagFactory: (String, Map<String, String>, String) -> Unit): Int {
+        return when (val closeIndex = input.indexOf('>', startIndex = startIndex)) {
+            -1 -> -1
+            else -> {
+                val fullTag = input.substring(startIndex, closeIndex + 1)
+                val tagName = input.substring(startIndex + 1, closeIndex)
+                when {
+                    fullTag.isExitlessTag() -> {
+                        val trim = fullTag.removeSurrounding("<", ">").trim()
+                        tagFactory(trim, emptyMap(), "")
+                        closeIndex + 1
+                    }
+
+                    fullTag.isSelfClosing() -> {
+                        val trim = fullTag.removeSuffix("/>").removePrefix("<").trim()
+                        tagFactory(trim, emptyMap(), "")
+                        closeIndex + 1
+                    }
+
+                    else -> {
+                        val exitTag = if (tagName.contains(' ')) {
+                            "</${tagName.substringBefore(' ')}>"
+                        } else {
+                            "</$tagName>"
+                        }
+
+                        val exitIndex = input.findTagClose(tagName, exitTag, searchIndex = closeIndex + 1)
+                        if (exitIndex == -1) {
+                            -1
+                        } else {
+                            val exitTagCloseIndex = exitIndex + exitTag.length
+                            if (tagName.contains(' ')) {
+                                val parts = tagName.split(' ')
+                                val attributes = parts.drop(1).associate {
+                                    val (key, value) = it.split("=")
+                                    key to value.removeSurrounding("\"")
+                                }
+                                tagFactory(parts.first(), attributes, input.substring(closeIndex + 1, exitIndex))
+                            } else {
+                                tagFactory(tagName, emptyMap(), input.substring(closeIndex + 1, exitIndex))
+                            }
+                            exitTagCloseIndex
+                        }
+                    }
+                }
+            }
+        }
+    }
+
+    private fun String.findTagClose(tagName: String, exitTag: String, searchIndex: Int, open: Int = 1): Int {
+        val exitIndex = this.indexOf(exitTag, startIndex = searchIndex)
+        val nextOpen = this.indexOf("<$tagName", startIndex = searchIndex)
+        return when {
+            open == 1 && (nextOpen == -1 || exitIndex < nextOpen) -> exitIndex
+            open > 8 || open < 1 -> {
+                // something has gone wrong, lets exit
+                -1
+            }
+
+            exitIndex == -1 -> -1
+            nextOpen == -1 || nextOpen > exitIndex -> this.findTagClose(tagName, exitTag, exitIndex + 1, open - 1)
+
+            nextOpen < exitIndex -> {
+                this.findTagClose(tagName, exitTag, nextOpen + 1, open + 1)
+            }
+
+            else -> -1
+        }
+    }
+}
+
+private fun String.isExitlessTag() = this == "<br>" || (this.startsWith("<@") && this.endsWith('>'))
+
+private fun String.isSelfClosing() = this.endsWith("/>")
diff --git a/matrix/services/sync/src/main/kotlin/app/dapk/st/matrix/sync/internal/sync/message/UrlParser.kt b/matrix/services/sync/src/main/kotlin/app/dapk/st/matrix/sync/internal/sync/message/url/UrlParser.kt
similarity index 59%
rename from matrix/services/sync/src/main/kotlin/app/dapk/st/matrix/sync/internal/sync/message/UrlParser.kt
rename to matrix/services/sync/src/main/kotlin/app/dapk/st/matrix/sync/internal/sync/message/url/UrlParser.kt
index 9366120..290e05e 100644
--- a/matrix/services/sync/src/main/kotlin/app/dapk/st/matrix/sync/internal/sync/message/UrlParser.kt
+++ b/matrix/services/sync/src/main/kotlin/app/dapk/st/matrix/sync/internal/sync/message/url/UrlParser.kt
@@ -1,18 +1,14 @@
-package app.dapk.st.matrix.sync.internal.sync.message
+package app.dapk.st.matrix.sync.internal.sync.message.url
 
+import app.dapk.st.matrix.sync.internal.sync.message.ContentAccumulator
+
+private const val END_SEARCH = -1
 private const val INVALID_TRAILING_CHARS = ",.:;?<>"
 
 internal class UrlParser {
 
-    private fun String.hasLookAhead(current: Int, value: String): Boolean {
-        return length > current + value.length && this.substring(current, current + value.length) == value
-    }
-
-    fun parseUrl(input: String, linkStartIndex: Int, builder: PartBuilder): Int {
-        val urlIndex = input.indexOf("http", startIndex = linkStartIndex)
+    fun parseUrl(input: String, urlIndex: Int, accumulator: ContentAccumulator): Int {
         return if (urlIndex == END_SEARCH) END_SEARCH else {
-            builder.appendTextBeforeTag(linkStartIndex, urlIndex, input)
-
             val originalUrl = input.substring(urlIndex)
             var index = 0
             val maybeUrl = originalUrl.takeWhile {
@@ -25,29 +21,27 @@ internal class UrlParser {
             when {
                 urlContinuesUntilEnd -> {
                     val cleanedUrl = originalUrl.bestGuessStripTrailingUrlChar()
-                    builder.appendLink(url = cleanedUrl, label = null)
+                    accumulator.appendLink(url = cleanedUrl, label = null)
                     if (cleanedUrl != originalUrl) {
-                        builder.appendText(originalUrl.last().toString())
+                        accumulator.appendText(originalUrl.last().toString())
                     }
-                    input.length.next()
+                    input.length + 1
                 }
 
                 else -> {
                     val originalUrl = input.substring(urlIndex, urlEndIndex)
                     val cleanedUrl = originalUrl.bestGuessStripTrailingUrlChar()
-                    builder.appendLink(url = cleanedUrl, label = null)
+                    accumulator.appendLink(url = cleanedUrl, label = null)
                     if (originalUrl == cleanedUrl) urlEndIndex else urlEndIndex - 1
                 }
             }
         }
     }
-
-    fun test(startingFrom: Int, input: String): Int {
-        return input.indexOf("http", startingFrom)
-    }
-
 }
 
+private fun String.hasLookAhead(current: Int, value: String): Boolean {
+    return length > current + value.length && this.substring(current, current + value.length) == value
+}
 
 private fun String.bestGuessStripTrailingUrlChar(): String {
     val last = this.last()
diff --git a/matrix/services/sync/src/test/kotlin/app/dapk/st/matrix/sync/internal/sync/RichMessageParserTest.kt b/matrix/services/sync/src/test/kotlin/app/dapk/st/matrix/sync/internal/sync/RichTextMessageParserTest.kt
similarity index 91%
rename from matrix/services/sync/src/test/kotlin/app/dapk/st/matrix/sync/internal/sync/RichMessageParserTest.kt
rename to matrix/services/sync/src/test/kotlin/app/dapk/st/matrix/sync/internal/sync/RichTextMessageParserTest.kt
index 796dcfd..54c8369 100644
--- a/matrix/services/sync/src/test/kotlin/app/dapk/st/matrix/sync/internal/sync/RichMessageParserTest.kt
+++ b/matrix/services/sync/src/test/kotlin/app/dapk/st/matrix/sync/internal/sync/RichTextMessageParserTest.kt
@@ -5,10 +5,9 @@ import app.dapk.st.matrix.common.RichText.Part.*
 import app.dapk.st.matrix.sync.internal.sync.message.RichMessageParser
 import fixture.aUserId
 import org.amshove.kluent.shouldBeEqualTo
-import org.junit.Ignore
 import org.junit.Test
 
-class RichMessageParserTest {
+class RichTextMessageParserTest {
 
     private val parser = RichMessageParser()
 
@@ -18,6 +17,34 @@ class RichMessageParserTest {
         expected = RichText(listOf(Normal("Hello world!")))
     )
 
+    @Test
+    fun `parses strong tags`() = runParserTest(
+        Case(
+            input = """hello <strong>wor</strong>ld""",
+            expected = RichText(
+                listOf(
+                    Normal("hello "),
+                    Bold("wor"),
+                    Normal("ld"),
+                )
+            )
+        ),
+    )
+
+    @Test
+    fun `parses em tags`() = runParserTest(
+        Case(
+            input = """hello <em>wor</em>ld""",
+            expected = RichText(
+                listOf(
+                    Normal("hello "),
+                    Italic("wor"),
+                    Normal("ld"),
+                )
+            )
+        ),
+    )
+
     @Test
     fun `parses p tags`() = runParserTest(
         input = "<p>Hello world!</p><p>foo bar</p>after paragraph",
@@ -63,7 +90,7 @@ class RichMessageParserTest {
     @Test
     fun `replaces matrixdotto with person`() = runParserTest(
         input = """Hello <a href="https://matrix.to/#/@a-name:foo.bar">a-name</a>: world""",
-        expected = RichText(listOf(Normal("Hello "), Person(aUserId("@a-name:foo.bar"), "@a-name"), Normal(" world")))
+        expected = RichText(listOf(Normal("Hello "), Person(aUserId("@a-name:foo.bar"), "@a-name"), Normal(": world")))
     )
 
     @Test
@@ -122,6 +149,21 @@ class RichMessageParserTest {
         ),
     )
 
+
+    @Test
+    fun `parses nested lists`() = runParserTest(
+        input = """
+            <ul>
+            <li>first item
+                <ul>
+                    <li>nested item</li>
+                </ul>
+            </li>
+            </ul>
+        """.trimIndent().lines().joinToString("") { it.trim() },
+        expected = RichText(listOf(Normal("- first item\n- nested item")))
+    )
+
     @Test
     fun `parses urls`() = runParserTest(
         Case(
@@ -178,58 +220,6 @@ class RichMessageParserTest {
         expected = RichText(listOf(Normal(">><foo> ><>> << more content")))
     )
 
-    @Test
-    fun `parses strong tags`() = runParserTest(
-        Case(
-            input = """hello <strong>wor</strong>ld""",
-            expected = RichText(
-                listOf(
-                    Normal("hello "),
-                    Bold("wor"),
-                    Normal("ld"),
-                )
-            )
-        ),
-    )
-
-    @Test
-    fun `parses em tags`() = runParserTest(
-        Case(
-            input = """hello <em>wor</em>ld""",
-            expected = RichText(
-                listOf(
-                    Normal("hello "),
-                    Italic("wor"),
-                    Normal("ld"),
-                )
-            )
-        ),
-    )
-
-    @Ignore // TODO
-    @Test
-    fun `parses nested tags`() = runParserTest(
-        Case(
-            input = """hello <b><i>wor<i/><b/>ld""",
-            expected = RichText(
-                listOf(
-                    Normal("hello "),
-                    BoldItalic("wor"),
-                    Normal("ld"),
-                )
-            )
-        ),
-        Case(
-            input = """<a href="www.google.com"><a href="www.google.com">www.google.com<a/><a/>""",
-            expected = RichText(
-                listOf(
-                    Link(url = "www.google.com", label = "www.google.com"),
-                    Link(url = "www.bing.com", label = "www.bing.com"),
-                )
-            )
-        )
-    )
-
     @Test
     fun `parses 'a' tags`() = runParserTest(
         Case(