diff --git a/aztec/src/main/kotlin/org/wordpress/aztec/AztecText.kt b/aztec/src/main/kotlin/org/wordpress/aztec/AztecText.kt
index e07f91646..6e3132543 100644
--- a/aztec/src/main/kotlin/org/wordpress/aztec/AztecText.kt
+++ b/aztec/src/main/kotlin/org/wordpress/aztec/AztecText.kt
@@ -2275,7 +2275,6 @@ open class AztecText : AppCompatEditText, TextWatcher, UnknownHtmlSpan.OnUnknown
         text.getSpans(0, text.length, AztecMediaSpan::class.java).firstOrNull {
             attributePredicate.matches(it.attributes)
         }?.let { mediaSpan ->
-            mediaSpan.beforeMediaDeleted()
             val start = text.getSpanStart(mediaSpan)
             val end = text.getSpanEnd(mediaSpan)
 
@@ -2283,7 +2282,6 @@ open class AztecText : AppCompatEditText, TextWatcher, UnknownHtmlSpan.OnUnknown
 
             text.removeSpan(clickableSpan)
             text.removeSpan(mediaSpan)
-            mediaSpan.onMediaDeleted()
             aztecMediaSpan.onMediaDeletedListener = onMediaDeletedListener
             lineBlockFormatter.insertMediaSpanOverCurrentChar(aztecMediaSpan, start)
             contentChangeWatcher.notifyContentChanged()
diff --git a/build.gradle b/build.gradle
index bf09f0cef..b1570d08d 100644
--- a/build.gradle
+++ b/build.gradle
@@ -70,7 +70,7 @@ ext {
 
 ext {
     gradlePluginVersion = '3.3.1'
-    kotlinCoroutinesVersion = '1.1.0'
+    kotlinCoroutinesVersion = '1.6.4'
     tagSoupVersion = '1.2.1'
     glideVersion = '4.10.0'
     picassoVersion = '2.5.2'
diff --git a/media-placeholders/src/main/java/org/wordpress/aztec/placeholders/ImageWithCaptionAdapter.kt b/media-placeholders/src/main/java/org/wordpress/aztec/placeholders/ImageWithCaptionAdapter.kt
index e3f5d8eff..cae1957d0 100644
--- a/media-placeholders/src/main/java/org/wordpress/aztec/placeholders/ImageWithCaptionAdapter.kt
+++ b/media-placeholders/src/main/java/org/wordpress/aztec/placeholders/ImageWithCaptionAdapter.kt
@@ -81,8 +81,10 @@ class ImageWithCaptionAdapter(
         private const val CAPTION_ATTRIBUTE = "caption"
         private const val SRC_ATTRIBUTE = "src"
 
-        suspend fun insertImageWithCaption(placeholderManager: PlaceholderManager, src: String, caption: String) {
-            placeholderManager.insertOrUpdateItem(ADAPTER_TYPE) { currentAttributes, type, placeAtStart ->
+        suspend fun insertImageWithCaption(placeholderManager: PlaceholderManager, src: String, caption: String, shouldMergePlaceholders: Boolean = true) {
+            placeholderManager.insertOrUpdateItem(ADAPTER_TYPE, {
+                shouldMergePlaceholders
+            }) { currentAttributes, type, placeAtStart ->
                 if (currentAttributes == null || type != ADAPTER_TYPE) {
                     mapOf(SRC_ATTRIBUTE to src, CAPTION_ATTRIBUTE to caption)
                 } else {
diff --git a/media-placeholders/src/main/java/org/wordpress/aztec/placeholders/PlaceholderManager.kt b/media-placeholders/src/main/java/org/wordpress/aztec/placeholders/PlaceholderManager.kt
index c519ef640..c4898c100 100644
--- a/media-placeholders/src/main/java/org/wordpress/aztec/placeholders/PlaceholderManager.kt
+++ b/media-placeholders/src/main/java/org/wordpress/aztec/placeholders/PlaceholderManager.kt
@@ -123,8 +123,19 @@ class PlaceholderManager(
         val targetItem = getTargetItem()
         val targetSpan = targetItem?.span
         val currentType = targetSpan?.attributes?.getValue(TYPE_ATTRIBUTE)
-        if (currentType != null && shouldMergeItem(currentType)) {
-            updateSpan(type, targetItem.span, targetItem.placeAtStart, updateItem, currentType)
+        if (currentType != null) {
+            if (shouldMergeItem(currentType)) {
+                updateSpan(type, targetItem.span, targetItem.placeAtStart, updateItem, currentType)
+            } else {
+                val (newLinePosition, targetSelection) = if (targetItem.placeAtStart) {
+                    targetItem.spanStart to targetItem.spanStart
+                } else {
+                    targetItem.spanEnd to targetItem.spanEnd + 2
+                }
+                aztecText.text.insert(newLinePosition, Constants.NEWLINE_STRING)
+                aztecText.setSelection(targetSelection)
+                insertItem(type, *updateItem(null, null, false).toList().toTypedArray())
+            }
         } else {
             insertItem(type, *updateItem(null, null, false).toList().toTypedArray())
         }
@@ -192,7 +203,7 @@ class PlaceholderManager(
         return true
     }
 
-    private data class TargetItem(val span: AztecPlaceholderSpan, val placeAtStart: Boolean)
+    private data class TargetItem(val span: AztecPlaceholderSpan, val placeAtStart: Boolean, val spanStart: Int, val spanEnd: Int)
 
     private fun getTargetItem(): TargetItem? {
         if (aztecText.length() == 0) {
@@ -224,7 +235,7 @@ class PlaceholderManager(
                 from,
                 to,
                 AztecPlaceholderSpan::class.java
-        ).map { TargetItem(it, placeAtStart) }.lastOrNull()
+        ).map { TargetItem(it, placeAtStart, editableText.getSpanStart(it), editableText.getSpanEnd(it)) }.lastOrNull()
     }
 
     /**
@@ -286,7 +297,6 @@ class PlaceholderManager(
             }
         }
         val targetPosition = aztecText.getElementPosition(predicate) ?: return
-
         insertInPosition(aztecAttributes ?: return, targetPosition)
     }
 
@@ -318,39 +328,51 @@ class PlaceholderManager(
         parentTextViewRect.top += parentTextViewTopAndBottomOffset
         parentTextViewRect.bottom = parentTextViewRect.top + height
 
-        positionToIdMutex.withLock {
-            positionToId.removeAll {
-                it.uuid == uuid
+        var box = container.findViewWithTag<View>(uuid)?.apply {
+            id = uuid.hashCode()
+        }
+        val newWidth = adapter.calculateWidth(attrs, windowWidth) - EDITOR_INNER_PADDING
+        val newHeight = height - EDITOR_INNER_PADDING
+        val padding = 10
+        val newLeftPadding = parentTextViewRect.left + padding + aztecText.paddingStart
+        val newTopPadding = parentTextViewRect.top + padding
+        box?.let { existingView ->
+            val currentParams = existingView.layoutParams as FrameLayout.LayoutParams
+            val widthSame = currentParams.width == newWidth
+            val heightSame = currentParams.height == newHeight
+            val topMarginSame = currentParams.topMargin == newTopPadding
+            val leftMarginSame = currentParams.leftMargin == newLeftPadding
+            if (widthSame && heightSame && topMarginSame && leftMarginSame) {
+                return
+            }
+            container.removeView(box)
+            positionToIdMutex.withLock {
+                positionToId.removeAll {
+                    it.uuid == uuid
+                }
             }
         }
+        box = adapter.createView(container.context, uuid, attrs)
 
-        var box = container.findViewWithTag<View>(uuid)
-        val exists = box != null
-        if (!exists) {
-            box = adapter.createView(container.context, uuid, attrs)
-        }
-        val params = FrameLayout.LayoutParams(
-                adapter.calculateWidth(attrs, windowWidth) - EDITOR_INNER_PADDING,
-                height - EDITOR_INNER_PADDING
-        )
-        val padding = 10
-        params.setMargins(
-                parentTextViewRect.left + padding + aztecText.paddingStart,
-                parentTextViewRect.top + padding,
-                0,
-                0
-        )
-        box.layoutParams = params
-        box.tag = uuid
+        box.id = uuid.hashCode()
         box.setBackgroundColor(Color.TRANSPARENT)
         box.setOnTouchListener(adapter)
+        box.tag = uuid
+        box.layoutParams = FrameLayout.LayoutParams(
+                newWidth,
+                newHeight
+        ).apply {
+            leftMargin = newLeftPadding
+            topMargin = newTopPadding
+        }
+
         positionToIdMutex.withLock {
             positionToId.add(Placeholder(targetPosition, uuid))
         }
-        if (!exists && box.parent == null) {
+        if (box.parent == null) {
             container.addView(box)
-            adapter.onViewCreated(box, uuid)
         }
+        adapter.onViewCreated(box, uuid)
     }
 
     private fun validateAttributes(attributes: AztecAttributes): Boolean {
@@ -418,7 +440,13 @@ class PlaceholderManager(
     /**
      * This method handled a `placeholder` tag found in the HTML. It creates a placeholder and inserts a view over it.
      */
-    override fun handleTag(opening: Boolean, tag: String, output: Editable, attributes: Attributes, nestingLevel: Int): Boolean {
+    override fun handleTag(
+            opening: Boolean,
+            tag: String,
+            output: Editable,
+            attributes: Attributes,
+            nestingLevel: Int
+    ): Boolean {
         if (opening) {
             val type = attributes.getValue(TYPE_ATTRIBUTE)
             attributes.getValue(UUID_ATTRIBUTE)?.also { uuid ->
diff --git a/media-placeholders/src/test/java/org/wordpress/aztec/placeholders/PlaceholderTest.kt b/media-placeholders/src/test/java/org/wordpress/aztec/placeholders/PlaceholderTest.kt
index 1821227d9..a1efec8e3 100644
--- a/media-placeholders/src/test/java/org/wordpress/aztec/placeholders/PlaceholderTest.kt
+++ b/media-placeholders/src/test/java/org/wordpress/aztec/placeholders/PlaceholderTest.kt
@@ -27,7 +27,8 @@ class PlaceholderTest {
     lateinit var toolbar: AztecToolbar
     lateinit var placeholderManager: PlaceholderManager
 
-    private val uuid: String = "uuid123"
+    private val uuid1: String = "uuid1"
+    private val uuid2: String = "uuid2"
 
     /**
      * Initialize variables.
@@ -38,8 +39,9 @@ class PlaceholderTest {
         container = FrameLayout(activity)
         editText = AztecText(activity)
         container.addView(editText, FrameLayout.LayoutParams(MATCH_PARENT, MATCH_PARENT))
+        var counter = 0
         placeholderManager = PlaceholderManager(editText, container, generateUuid = {
-            uuid
+            listOf(uuid1, uuid2)[counter++]
         })
         placeholderManager.registerAdapter(ImageWithCaptionAdapter())
         editText.setCalypsoMode(false)
@@ -65,10 +67,10 @@ class PlaceholderTest {
             editText.setSelection(0)
             ImageWithCaptionAdapter.insertImageWithCaption(placeholderManager, "image.jpg", "Caption 123")
 
-            Assert.assertEquals("<placeholder uuid=\"$uuid\" type=\"image_with_caption\" src=\"image.jpg\" caption=\"Caption 123\" /><p>Line 1</p>", editText.toHtml())
+            Assert.assertEquals("<placeholder uuid=\"$uuid1\" type=\"image_with_caption\" src=\"image.jpg\" caption=\"Caption 123\" /><p>Line 1</p>", editText.toHtml())
 
             placeholderManager.removeItem {
-                it.getValue("uuid") == uuid
+                it.getValue("uuid") == uuid1
             }
 
             Assert.assertEquals(initialHtml, editText.toHtml())
@@ -85,10 +87,10 @@ class PlaceholderTest {
             editText.setSelection(editText.editableText.indexOf("1"))
             ImageWithCaptionAdapter.insertImageWithCaption(placeholderManager, "image.jpg", "Caption 123")
 
-            Assert.assertEquals("<p>Line 123<placeholder uuid=\"uuid123\" type=\"image_with_caption\" src=\"image.jpg\" caption=\"Caption 123\" /></p><p>Line 2</p>", editText.toHtml())
+            Assert.assertEquals("<p>Line 123<placeholder uuid=\"uuid1\" type=\"image_with_caption\" src=\"image.jpg\" caption=\"Caption 123\" /></p><p>Line 2</p>", editText.toHtml())
 
             placeholderManager.removeItem {
-                it.getValue("uuid") == uuid
+                it.getValue("uuid") == uuid1
             }
 
             Assert.assertEquals(initialHtml, editText.toHtml())
@@ -97,7 +99,7 @@ class PlaceholderTest {
 
     @Test
     @Throws(Exception::class)
-    fun insertOrUpdateAPlaceholderAtTheBeginning() {
+    fun updatePlaceholderAtTheBeginning() {
         runBlocking {
             val initialHtml = "<p>Line 1</p>"
             editText.fromHtml(initialHtml)
@@ -109,7 +111,7 @@ class PlaceholderTest {
             Assert.assertEquals("${placeholderWithCaption("Caption 1 - Caption 2")}<p>Line 1</p>", editText.toHtml())
 
             placeholderManager.removeItem {
-                it.getValue("uuid") == uuid
+                it.getValue("uuid") == uuid1
             }
 
             Assert.assertEquals(initialHtml, editText.toHtml())
@@ -118,7 +120,28 @@ class PlaceholderTest {
 
     @Test
     @Throws(Exception::class)
-    fun insertOrUpdateAPlaceholderWhenInsertingBeforeNewLine() {
+    fun doNotUpdatePlaceholderAtTheBeginningWhenMergeDisabled() {
+        runBlocking {
+            val initialHtml = "<p>Line 1</p>"
+            editText.fromHtml(initialHtml)
+
+            editText.setSelection(0)
+            ImageWithCaptionAdapter.insertImageWithCaption(placeholderManager, "image.jpg", "Caption 1")
+            ImageWithCaptionAdapter.insertImageWithCaption(placeholderManager, "image.jpg", "Caption 2", shouldMergePlaceholders = false)
+
+            Assert.assertEquals("<placeholder uuid=\"uuid1\" type=\"image_with_caption\" src=\"image.jpg\" caption=\"Caption 1\" /><br><placeholder uuid=\"uuid2\" type=\"image_with_caption\" src=\"image.jpg\" caption=\"Caption 2\" /><p>Line 1</p>", editText.toHtml())
+
+            placeholderManager.removeItem {
+                it.getValue("uuid") == uuid1
+            }
+
+            Assert.assertEquals("<br><placeholder uuid=\"uuid2\" type=\"image_with_caption\" src=\"image.jpg\" caption=\"Caption 2\" /><p>Line 1</p>", editText.toHtml())
+        }
+    }
+
+    @Test
+    @Throws(Exception::class)
+    fun updatePlaceholderWhenInsertingBeforeNewLine() {
         runBlocking {
             val initialHtml = "<p>Line 1</p>${placeholderWithCaption("First")}<p>Line 2</p>"
             editText.fromHtml(initialHtml)
@@ -132,7 +155,21 @@ class PlaceholderTest {
 
     @Test
     @Throws(Exception::class)
-    fun insertOrUpdateAPlaceholderWhenInsertingRightBefore() {
+    fun doNotUpdatePlaceholderWhenInsertingBeforeNewLineAndMergeDisabled() {
+        runBlocking {
+            val initialHtml = "<p>Line 1</p>${placeholderWithCaption("First")}<p>Line 2</p>"
+            editText.fromHtml(initialHtml)
+
+            editText.setSelection(editText.editableText.indexOf("1"))
+            ImageWithCaptionAdapter.insertImageWithCaption(placeholderManager, "image.jpg", "Second", shouldMergePlaceholders = false)
+
+            Assert.assertEquals("<p>Line 1</p><placeholder uuid=\"uuid2\" type=\"image_with_caption\" src=\"image.jpg\" caption=\"Second\" /><br><placeholder src=\"image.jpg\" caption=\"First\" uuid=\"uuid1\" type=\"image_with_caption\" /><p>Line 2</p>", editText.toHtml())
+        }
+    }
+
+    @Test
+    @Throws(Exception::class)
+    fun updatePlaceholderWhenInsertingRightBefore() {
         runBlocking {
             val initialHtml = "<p>Line 1</p>${placeholderWithCaption("First")}<p>Line 2</p>"
             editText.fromHtml(initialHtml)
@@ -144,18 +181,32 @@ class PlaceholderTest {
         }
     }
 
+    @Test
+    @Throws(Exception::class)
+    fun doNotUpdatePlaceholderWhenInsertingRightBeforeAndMergeDisabled() {
+        runBlocking {
+            val initialHtml = "<p>Line 1</p>${placeholderWithCaption("First")}<p>Line 2</p>"
+            editText.fromHtml(initialHtml)
+
+            editText.setSelection(editText.editableText.indexOf("1") + 1)
+            ImageWithCaptionAdapter.insertImageWithCaption(placeholderManager, "image.jpg", "Second", shouldMergePlaceholders = false)
+
+            Assert.assertEquals("<p>Line 1</p><placeholder uuid=\"uuid2\" type=\"image_with_caption\" src=\"image.jpg\" caption=\"Second\" /><br>${placeholderWithCaption("First")}<p>Line 2</p>", editText.toHtml())
+        }
+    }
+
     private fun placeholderWithCaption(caption: String): String {
-        return "<placeholder src=\"image.jpg\" caption=\"$caption\" uuid=\"uuid123\" type=\"image_with_caption\" />"
+        return "<placeholder src=\"image.jpg\" caption=\"$caption\" uuid=\"uuid1\" type=\"image_with_caption\" />"
     }
 
     @Test
     @Throws(Exception::class)
     fun updatePlaceholderWhenItShouldBe() {
         runBlocking {
-            val initialHtml = "<placeholder uuid=\"uuid123\" type=\"image_with_caption\" src=\"image.jpg;image2.jpg\" caption=\"Caption - 1, 2\" /><p>Line</p>"
+            val initialHtml = "<placeholder uuid=\"uuid1\" type=\"image_with_caption\" src=\"image.jpg;image2.jpg\" caption=\"Caption - 1, 2\" /><p>Line</p>"
             editText.fromHtml(initialHtml)
 
-            placeholderManager.removeOrUpdate("uuid123", shouldUpdateItem = {
+            placeholderManager.removeOrUpdate("uuid1", shouldUpdateItem = {
                 true
             }) { currentAttributes ->
                 val result = mutableMapOf<String, String>()
@@ -164,7 +215,7 @@ class PlaceholderTest {
                 result
             }
 
-            Assert.assertEquals("<placeholder src=\"image.jpg\" caption=\"Updated caption\" uuid=\"uuid123\" type=\"image_with_caption\" /><p>Line</p>", editText.toHtml())
+            Assert.assertEquals("<placeholder src=\"image.jpg\" caption=\"Updated caption\" uuid=\"uuid1\" type=\"image_with_caption\" /><p>Line</p>", editText.toHtml())
         }
     }
 
@@ -172,13 +223,13 @@ class PlaceholderTest {
     @Throws(Exception::class)
     fun updatePlaceholderAtTheEnd() {
         runBlocking {
-            val initialHtml = "<p>First Line</p><placeholder uuid=\"uuid123\" type=\"image_with_caption\" src=\"image.jpg;image2.jpg\" caption=\"Caption - 1, 2\" /><p>Second Line</p>"
+            val initialHtml = "<p>First Line</p><placeholder uuid=\"uuid1\" type=\"image_with_caption\" src=\"image.jpg;image2.jpg\" caption=\"Caption - 1, 2\" /><p>Second Line</p>"
             editText.fromHtml(initialHtml)
             editText.setSelection(editText.editableText.indexOf("First") + 1)
             val initialSelectionStart = editText.selectionStart
             val initialSelectionEnd = editText.selectionEnd
 
-            placeholderManager.removeOrUpdate("uuid123", shouldUpdateItem = {
+            placeholderManager.removeOrUpdate("uuid1", shouldUpdateItem = {
                 true
             }) { currentAttributes ->
                 val result = mutableMapOf<String, String>()
@@ -187,7 +238,7 @@ class PlaceholderTest {
                 result
             }
 
-            Assert.assertEquals("<p>First Line</p><placeholder src=\"image.jpg\" caption=\"Updated caption\" uuid=\"uuid123\" type=\"image_with_caption\" /><p>Second Line</p>", editText.toHtml())
+            Assert.assertEquals("<p>First Line</p><placeholder src=\"image.jpg\" caption=\"Updated caption\" uuid=\"uuid1\" type=\"image_with_caption\" /><p>Second Line</p>", editText.toHtml())
             Assert.assertEquals(initialSelectionStart, editText.selectionStart)
             Assert.assertEquals(initialSelectionEnd, editText.selectionEnd)
         }
@@ -197,10 +248,10 @@ class PlaceholderTest {
     @Throws(Exception::class)
     fun removePlaceholderWhenItShouldNotBeUpdated() {
         runBlocking {
-            val initialHtml = "<placeholder uuid=\"uuid123\" type=\"image_with_caption\" src=\"image.jpg;image2.jpg\" caption=\"Caption - 1, 2\" /><p>Line</p>"
+            val initialHtml = "<placeholder uuid=\"uuid1\" type=\"image_with_caption\" src=\"image.jpg;image2.jpg\" caption=\"Caption - 1, 2\" /><p>Line</p>"
             editText.fromHtml(initialHtml)
 
-            placeholderManager.removeOrUpdate("uuid123", shouldUpdateItem = {
+            placeholderManager.removeOrUpdate("uuid1", shouldUpdateItem = {
                 false
             }) { currentAttributes ->
                 val result = mutableMapOf<String, String>()