diff --git a/autotests/texthandlertest.cpp b/autotests/texthandlertest.cpp
index d56e4c379..2d2eed630 100644
--- a/autotests/texthandlertest.cpp
+++ b/autotests/texthandlertest.cpp
@@ -347,6 +347,9 @@ void TextHandlerTest::receiveStripNewlines()
     const QString testInputStringRich = QStringLiteral("Test<br>many<br />new<br>lines.");
     const QString testOutputString = QStringLiteral("Test many new lines.");
 
+    const QString testInputStringPlain2 = QStringLiteral("* List\n* Items");
+    const QString testOutputString2 = QStringLiteral("List Items");
+
     TextHandler testTextHandler;
     testTextHandler.setData(testInputStringPlain);
 
@@ -354,9 +357,11 @@ void TextHandlerTest::receiveStripNewlines()
     QCOMPARE(testTextHandler.handleRecieveRichText(Qt::PlainText, nullptr, nullptr, true), testOutputString);
 
     testTextHandler.setData(testInputStringRich);
-
     QCOMPARE(testTextHandler.handleRecievePlainText(Qt::RichText, true), testOutputString);
     QCOMPARE(testTextHandler.handleRecieveRichText(Qt::RichText, nullptr, nullptr, true), testOutputString);
+
+    testTextHandler.setData(testInputStringPlain2);
+    QCOMPARE(testTextHandler.handleRecievePlainText(Qt::RichText, true), testOutputString2);
 }
 
 /**
diff --git a/src/neochatroom.cpp b/src/neochatroom.cpp
index c9a655b43..bda530045 100644
--- a/src/neochatroom.cpp
+++ b/src/neochatroom.cpp
@@ -468,7 +468,7 @@ QString NeoChatRoom::eventToString(const RoomEvent &evt, Qt::TextFormat format,
                     fileCaption = e.plainBody() + " | " + fileCaption;
                 }
                 textHandler.setData(fileCaption);
-                return !fileCaption.isEmpty() ? textHandler.handleRecievePlainText() : i18n("a file");
+                return !fileCaption.isEmpty() ? textHandler.handleRecievePlainText(Qt::PlainText, stripNewlines) : i18n("a file");
             }
 
             QString body;
diff --git a/src/texthandler.cpp b/src/texthandler.cpp
index 102116f72..25a9f4eed 100644
--- a/src/texthandler.cpp
+++ b/src/texthandler.cpp
@@ -151,12 +151,6 @@ QString TextHandler::handleRecievePlainText(Qt::TextFormat inputFormat, const bo
     // Strip mx-reply if present.
     m_dataBuffer.remove(TextRegex::removeRichReply);
 
-    if (stripNewlines) {
-        m_dataBuffer.replace(QStringLiteral("<br>"), QStringLiteral(" "));
-        m_dataBuffer.replace(QStringLiteral("<br />"), QStringLiteral(" "));
-        m_dataBuffer.replace(u'\n', QStringLiteral(" "));
-    }
-
     // Escaping then unescaping allows < and > to be maintained in a plain text string
     // otherwise markdownToHTML will strip what it thinks is a bad html tag entirely.
     if (inputFormat == Qt::PlainText) {
@@ -169,6 +163,14 @@ QString TextHandler::handleRecievePlainText(Qt::TextFormat inputFormat, const bo
      */
     m_dataBuffer = markdownToHTML(m_dataBuffer);
 
+    if (stripNewlines) {
+        m_dataBuffer.replace(QStringLiteral("<br>\n"), QStringLiteral(" "));
+        m_dataBuffer.replace(QStringLiteral("<br>"), QStringLiteral(" "));
+        m_dataBuffer.replace(QStringLiteral("<br />\n"), QStringLiteral(" "));
+        m_dataBuffer.replace(QStringLiteral("<br />"), QStringLiteral(" "));
+        m_dataBuffer.replace(u'\n', QStringLiteral(" "));
+    }
+
     // Strip all tags/attributes except code blocks which will be escaped.
     QString outputString;
     nextTokenType();
@@ -193,6 +195,7 @@ QString TextHandler::handleRecievePlainText(Qt::TextFormat inputFormat, const bo
         outputString = unescapeHtml(outputString);
     }
 
+    outputString = outputString.trimmed();
     return outputString;
 }