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
index d855bb2..f9e2e0f 100644
--- 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
@@ -24,68 +24,27 @@ internal class HtmlParser {
 
                 tagName == "br" -> {
                     appendTextBeforeTag(searchIndex, tagOpen, builder, input)
-                    builder.appendText("\n")
+                    builder.appendNewline()
                     tagClose.next()
                 }
 
                 else -> {
                     val exitTag = "</$tagName>"
                     val exitIndex = input.indexOf(exitTag, startIndex = tagClose)
-                    val exitTagClose = exitIndex + exitTag.length
+                    val exitTagCloseIndex = exitIndex + exitTag.length
                     if (exitIndex == END_SEARCH) {
                         builder.appendText(input[searchIndex].toString())
                         searchIndex.next()
                     } else {
                         when (tagName) {
                             "mx-reply" -> {
-                                exitTagClose
+                                exitTagCloseIndex
                             }
 
                             else -> {
                                 appendTextBeforeTag(searchIndex, tagOpen, builder, input)
                                 val tagContent = input.substring(tagClose + 1, exitIndex)
-                                when (tagName) {
-                                    "a" -> {
-                                        val findHrefUrl = wholeTag.substringAfter("href=").replace("\"", "").removeSuffix(">")
-                                        if (findHrefUrl.startsWith("https://matrix.to/#/@")) {
-                                            val userId = UserId(findHrefUrl.substringAfter("https://matrix.to/#/").substringBeforeLast("\""))
-                                            builder.appendPerson(userId, "@${tagContent.removePrefix("@")}")
-                                            if (input.getOrNull(exitTagClose) == ':') {
-                                                exitTagClose.next()
-                                            } else {
-                                                exitTagClose
-                                            }
-                                        } else {
-                                            builder.appendLink(findHrefUrl, label = tagContent)
-                                            exitTagClose
-                                        }
-                                    }
-
-                                    "b" -> {
-                                        builder.appendBold(tagContent)
-                                        exitTagClose
-                                    }
-
-                                    "strong" -> {
-                                        builder.appendBold(tagContent)
-                                        exitTagClose
-                                    }
-
-                                    "i" -> {
-                                        builder.appendItalic(tagContent)
-                                        exitTagClose
-                                    }
-
-                                    "em" -> {
-                                        builder.appendItalic(tagContent)
-                                        exitTagClose
-                                    }
-
-                                    else -> {
-                                        builder.appendText(tagContent)
-                                        exitTagClose
-                                    }
-                                }
+                                handleTagWithContent(input, tagName, wholeTag, builder, tagContent, exitTagCloseIndex)
                             }
                         }
                     }
@@ -94,6 +53,65 @@ internal class HtmlParser {
         }
     )
 
+    private fun handleTagWithContent(
+        input: String,
+        tagName: String,
+        wholeTag: String,
+        builder: PartBuilder,
+        tagContent: String,
+        exitTagCloseIndex: Int
+    ) = when (tagName) {
+        "a" -> {
+            val findHrefUrl = wholeTag.substringAfter("href=").replace("\"", "").removeSuffix(">")
+            if (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" -> {
+            builder.appendBold(tagContent)
+            exitTagCloseIndex
+        }
+
+        "p" -> {
+            builder.appendText(tagContent)
+            builder.appendNewline()
+            builder.appendNewline()
+            exitTagCloseIndex
+        }
+
+        "strong" -> {
+            builder.appendBold(tagContent)
+            exitTagCloseIndex
+        }
+
+        "i" -> {
+            builder.appendItalic(tagContent)
+            exitTagCloseIndex
+        }
+
+        "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))
@@ -115,4 +133,8 @@ internal class HtmlParser {
         }
     }
 
+    fun test(startingFrom: Int, intput: String): Int {
+        return intput.indexOf('<', startingFrom)
+    }
+
 }
\ No newline at end of file
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/PartBuilder.kt
index db3c93b..ab34699 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/PartBuilder.kt
@@ -54,3 +54,8 @@ internal fun PartBuilder.appendTextBeforeTag(previousIndex: Int, tagOpenIndex: I
         this.appendText(input.substring(previousIndex, tagOpenIndex))
     }
 }
+
+internal fun PartBuilder.appendNewline() {
+    this.appendText("\n")
+}
+
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
index 2d68b78..ac537da 100644
--- 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
@@ -17,15 +17,27 @@ class RichMessageParser {
         val builder = PartBuilder()
         var nextIndex = 0
         while (nextIndex != END_SEARCH) {
-            val htmlResult = htmlParser.parseHtmlTags(input, nextIndex, builder)
-            val linkStartIndex = findUrlStartIndex(htmlResult, nextIndex)
-            val urlResult = urlParser.parseUrl(input, linkStartIndex, builder)
+            val htmlStart = htmlParser.test(nextIndex, input)
+            val urlStart = urlParser.test(nextIndex, input)
 
-            val hasReachedEnd = hasReachedEnd(htmlResult, urlResult, input)
-            if (hasReachedEnd && hasUnprocessedText(htmlResult, urlResult, 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))
             }
-            nextIndex = if (hasReachedEnd) END_SEARCH else max(htmlResult, urlResult)
+            nextIndex = if (hasReachedEnd) END_SEARCH else max(firstResult, secondResult)
         }
         return RichText(builder.build())
     }
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/UrlParser.kt
index a37869e..9366120 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/UrlParser.kt
@@ -1,16 +1,25 @@
 package app.dapk.st.matrix.sync.internal.sync.message
 
-private const val INVALID_TRAILING_CHARS = ",.:;?"
+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)
-        val urlResult = if (urlIndex == END_SEARCH) END_SEARCH else {
+        return if (urlIndex == END_SEARCH) END_SEARCH else {
             builder.appendTextBeforeTag(linkStartIndex, urlIndex, input)
 
             val originalUrl = input.substring(urlIndex)
-            val urlEndIndex = originalUrl.indexOfFirst { it == '\n' || it == ' ' }
+            var index = 0
+            val maybeUrl = originalUrl.takeWhile {
+                it != '\n' && it != ' ' && !originalUrl.hasLookAhead(index++, "<br")
+            }
+
+            val urlEndIndex = maybeUrl.length + urlIndex
             val urlContinuesUntilEnd = urlEndIndex == -1
 
             when {
@@ -31,7 +40,10 @@ internal class UrlParser {
                 }
             }
         }
-        return urlResult
+    }
+
+    fun test(startingFrom: Int, input: String): Int {
+        return input.indexOf("http", startingFrom)
     }
 
 }
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/RichMessageParserTest.kt
index 3cf80f8..7f8f01e 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/RichMessageParserTest.kt
@@ -19,9 +19,9 @@ class RichMessageParserTest {
     )
 
     @Test
-    fun `skips p tags`() = runParserTest(
-        input = "Hello world! <p>foo bar</p> after paragraph",
-        expected = RichText(setOf(Normal("Hello world! foo bar after paragraph")))
+    fun `parses p tags`() = runParserTest(
+        input = "<p>Hello world!</p><p>foo bar</p>after paragraph",
+        expected = RichText(setOf(Normal("Hello world!\n\nfoo bar\n\nafter paragraph")))
     )
 
     @Test
@@ -84,6 +84,10 @@ class RichMessageParserTest {
             input = "ending sentence with url https://google.com.",
             expected = RichText(setOf(Normal("ending sentence with url "), Link("https://google.com", "https://google.com"), Normal(".")))
         ),
+        Case(
+            input = "https://google.com<br>html after url",
+            expected = RichText(setOf(Link("https://google.com", "https://google.com"), Normal("\nhtml after url")))
+        ),
     )
 
     @Test
diff --git a/matrix/services/sync/src/test/kotlin/app/dapk/st/matrix/sync/internal/sync/RoomEventCreatorTest.kt b/matrix/services/sync/src/test/kotlin/app/dapk/st/matrix/sync/internal/sync/RoomEventCreatorTest.kt
index 6f11704..9932bc7 100644
--- a/matrix/services/sync/src/test/kotlin/app/dapk/st/matrix/sync/internal/sync/RoomEventCreatorTest.kt
+++ b/matrix/services/sync/src/test/kotlin/app/dapk/st/matrix/sync/internal/sync/RoomEventCreatorTest.kt
@@ -111,7 +111,7 @@ internal class RoomEventCreatorTest {
         result shouldBeEqualTo aMatrixRoomMessageEvent(
             eventId = editEvent.id,
             utcTimestamp = editEvent.utcTimestamp,
-            content = RichText.of(editEvent.asTextContent().body!!),
+            content = RichText.of(editEvent.asTextContent().body!!.trimStart()),
             author = A_SENDER,
             edited = true
         )