diff --git a/aztec/src/main/kotlin/org/wordpress/aztec/formatting/BlockFormatter.kt b/aztec/src/main/kotlin/org/wordpress/aztec/formatting/BlockFormatter.kt
index 700def0d6..0a775c95c 100644
--- a/aztec/src/main/kotlin/org/wordpress/aztec/formatting/BlockFormatter.kt
+++ b/aztec/src/main/kotlin/org/wordpress/aztec/formatting/BlockFormatter.kt
@@ -317,8 +317,8 @@ class BlockFormatter(editor: AztecText, val listStyle: ListStyle, val quoteStyle
             if (numberOfLines == numberOfLinesWithSpanApplied) {
                 removeBlockStyle(blockElementType)
             } else {
-                applyBlock(blockElementType, startOfBlock + 1,
-                        (if (endOfBlock == editableText.length) endOfBlock else endOfBlock + 1), nestingLevel)
+                applyBlock(makeBlockSpan(blockElementType, nestingLevel), startOfBlock + 1,
+                        (if (endOfBlock == editableText.length) endOfBlock else endOfBlock + 1))
             }
 
         } else {
@@ -327,31 +327,39 @@ class BlockFormatter(editor: AztecText, val listStyle: ListStyle, val quoteStyle
             val startOfLine = boundsOfSelectedText.start
             val endOfLine = boundsOfSelectedText.endInclusive
 
-            val spanToApply = getOuterBlockSpanType(blockElementType)
+            val nestingLevel = AztecNestable.getNestingLevelAt(editableText, start) + 1
+
+            val spanToApply = makeBlockSpan(blockElementType, nestingLevel)
 
             var startOfBlock: Int = startOfLine
             var endOfBlock: Int = endOfLine
 
 
             if (startOfLine != 0) {
-                val spansOnPreviousLine = editableText.getSpans(startOfLine - 1, startOfLine - 1, spanToApply).firstOrNull()
-                if (spansOnPreviousLine != null) {
+                val spansOnPreviousLine = editableText.getSpans(startOfLine - 1, startOfLine - 1, spanToApply.javaClass)
+                        .firstOrNull()
+                // if same span type is found (also check for heading style equality if a heading) extend the start
+                if (spansOnPreviousLine != null
+                        && (spansOnPreviousLine !is AztecHeadingSpan
+                                || spansOnPreviousLine.heading == (spanToApply as AztecHeadingSpan).heading)) {
                     startOfBlock = editableText.getSpanStart(spansOnPreviousLine)
                     liftBlock(blockElementType, startOfBlock, endOfBlock)
                 }
             }
 
             if (endOfLine != editableText.length) {
-                val spanOnNextLine = editableText.getSpans(endOfLine + 1, endOfLine + 1, spanToApply).firstOrNull()
-                if (spanOnNextLine != null) {
+                val spanOnNextLine = editableText.getSpans(endOfLine + 1, endOfLine + 1, spanToApply.javaClass)
+                        .firstOrNull()
+                // if same span type is found (also check for heading style equality if a heading) extend the end
+                if (spanOnNextLine != null
+                        && (spanOnNextLine !is AztecHeadingSpan
+                                || spanOnNextLine.heading == (spanToApply as AztecHeadingSpan).heading)) {
                     endOfBlock = editableText.getSpanEnd(spanOnNextLine)
                     liftBlock(blockElementType, startOfBlock, endOfBlock)
                 }
             }
 
-            val nestingLevel = AztecNestable.getNestingLevelAt(editableText, start) + 1
-
-            applyBlock(blockElementType, startOfBlock, endOfBlock, nestingLevel)
+            applyBlock(spanToApply, startOfBlock, endOfBlock)
 
             //if the line was empty trigger onSelectionChanged manually to update toolbar buttons status
 //            if (isEmptyLine) {
@@ -360,22 +368,17 @@ class BlockFormatter(editor: AztecText, val listStyle: ListStyle, val quoteStyle
         }
     }
 
-    private fun applyBlock(textFormat: TextFormat, start: Int, end: Int, nestingLevel: Int, attrs: String = "") {
-        when (textFormat) {
-            TextFormat.FORMAT_ORDERED_LIST -> applyListBlock(AztecOrderedListSpan(nestingLevel, attrs, listStyle), start, end, nestingLevel)
-            TextFormat.FORMAT_UNORDERED_LIST -> applyListBlock(AztecUnorderedListSpan(nestingLevel, attrs, listStyle), start, end, nestingLevel)
-            TextFormat.FORMAT_QUOTE -> BlockHandler.set(editableText, AztecQuoteSpan(nestingLevel, attrs, quoteStyle), start, end)
-            TextFormat.FORMAT_HEADING_1,
-            TextFormat.FORMAT_HEADING_2,
-            TextFormat.FORMAT_HEADING_3,
-            TextFormat.FORMAT_HEADING_4,
-            TextFormat.FORMAT_HEADING_5,
-            TextFormat.FORMAT_HEADING_6 -> applyHeadingBlock(AztecHeadingSpan(nestingLevel, textFormat, attrs, headerStyle), start, end, nestingLevel)
-            else -> editableText.setSpan(ParagraphSpan(nestingLevel, attrs), start, end, Spanned.SPAN_PARAGRAPH)
+    private fun applyBlock(blockSpan: AztecBlockSpan, start: Int, end: Int) {
+        when (blockSpan) {
+            is AztecOrderedListSpan -> applyListBlock(blockSpan, start, end)
+            is AztecUnorderedListSpan -> applyListBlock(blockSpan, start, end)
+            is AztecQuoteSpan -> BlockHandler.set(editableText, blockSpan, start, end)
+            is AztecHeadingSpan -> applyHeadingBlock(blockSpan, start, end)
+            else -> editableText.setSpan(blockSpan, start, end, Spanned.SPAN_PARAGRAPH)
         }
     }
 
-    private fun applyListBlock(listSpan: AztecListSpan, start: Int, end: Int, nestingLevel: Int) {
+    private fun applyListBlock(listSpan: AztecListSpan, start: Int, end: Int) {
         BlockHandler.set(editableText, listSpan, start, end)
 
         val lines = TextUtils.split(editableText.substring(start, end), "\n")
@@ -389,23 +392,22 @@ class BlockFormatter(editor: AztecText, val listStyle: ListStyle, val quoteStyle
 
             if (lineLength == 0) continue
 
-            ListItemHandler.newListItem(editableText, start + lineStart, start + lineEnd, nestingLevel + 1)
+            ListItemHandler.newListItem(editableText, start + lineStart, start + lineEnd, listSpan.nestingLevel + 1)
         }
     }
 
-    private fun applyHeadingBlock(headingSpan: AztecHeadingSpan, start: Int, end: Int, nestingLevel: Int) {
+    private fun applyHeadingBlock(headingSpan: AztecHeadingSpan, start: Int, end: Int) {
         val lines = TextUtils.split(editableText.substring(start, end), "\n")
         for (i in lines.indices) {
-            val lineLength = lines[i].length
+            val splitLength = lines[i].length
 
-            val lineStart = (0..i - 1).sumBy { lines[it].length + 1 }
-            val lineEnd = (lineStart + lineLength).let {
-                if ((start + it) != editableText.length) it + 1 else it // include the newline or not
-            }
+            val lineStart = start + (0..i - 1).sumBy { lines[it].length + 1 }
+            val lineEnd = Math.min(lineStart + splitLength + 1, end) // +1 to include the newline
 
+            val lineLength = lineEnd - lineStart
             if (lineLength == 0) continue
 
-            HeadingHandler.cloneHeading(editableText, headingSpan, start + lineStart, start + lineEnd)
+            HeadingHandler.cloneHeading(editableText, headingSpan, lineStart, lineEnd)
         }
     }
 
diff --git a/aztec/src/test/kotlin/org/wordpress/aztec/HeadingTest.kt b/aztec/src/test/kotlin/org/wordpress/aztec/HeadingTest.kt
index e09203d35..247b3f53d 100644
--- a/aztec/src/test/kotlin/org/wordpress/aztec/HeadingTest.kt
+++ b/aztec/src/test/kotlin/org/wordpress/aztec/HeadingTest.kt
@@ -247,4 +247,19 @@ class HeadingTest() {
         editText.text.delete(l - 1, l)
         Assert.assertEquals("<h1></h1>", editText.toHtml())
     }
-}
\ No newline at end of file
+
+    @Test
+    @Throws(Exception::class)
+    fun addHeading_issue289() {
+        editText.fromHtml("<h1>Heading 1</h1>")
+
+        safeAppend(editText, "\n")
+
+        editText.setSelection(safeLength(editText))
+        editText.toggleFormatting(TextFormat.FORMAT_HEADING_2)
+        Assert.assertEquals("<h1>Heading 1</h1><h2></h2>", editText.toHtml())
+
+        safeAppend(editText, "Heading 2")
+        Assert.assertEquals("<h1>Heading 1</h1><h2>Heading 2</h2>", editText.toHtml())
+    }
+}