diff --git a/app/src/androidTest/kotlin/org/wordpress/aztec/demo/Matchers.kt b/app/src/androidTest/kotlin/org/wordpress/aztec/demo/Matchers.kt
index 71bfc1759..7d7f3500a 100644
--- a/app/src/androidTest/kotlin/org/wordpress/aztec/demo/Matchers.kt
+++ b/app/src/androidTest/kotlin/org/wordpress/aztec/demo/Matchers.kt
@@ -7,16 +7,37 @@ import org.hamcrest.Matcher
 import org.hamcrest.TypeSafeMatcher
 
 object Matchers {
-    fun withRegex(regex: Regex): Matcher<View> {
+    fun withRegex(expected: Regex): Matcher<View> {
 
         return object : TypeSafeMatcher<View>() {
             override fun describeTo(description: Description) {
-                description.appendText("EditText matches $regex")
+                description.appendText("EditText matches $expected")
             }
 
             public override fun matchesSafely(view: View): Boolean {
                 if (view is EditText) {
-                    return view.text.toString().matches(regex)
+                    val regex = Regex(">\\s+<")
+                    val strippedText = view.text.toString().replace(regex, "><")
+                    return strippedText.matches(expected)
+                }
+
+                return false
+            }
+        }
+    }
+
+    fun withStrippedText(expected: String): Matcher<View> {
+
+        return object : TypeSafeMatcher<View>() {
+            override fun describeTo(description: Description) {
+                description.appendText("EditText matches $expected")
+            }
+
+            public override fun matchesSafely(view: View): Boolean {
+                if (view is EditText) {
+                    val regex = Regex(">\\s+<")
+                    val strippedText = view.text.toString().replace(regex, "><")
+                    return strippedText.equals(expected)
                 }
 
                 return false
diff --git a/app/src/androidTest/kotlin/org/wordpress/aztec/demo/pages/EditorPage.kt b/app/src/androidTest/kotlin/org/wordpress/aztec/demo/pages/EditorPage.kt
index 7db8cd579..a40c687ff 100644
--- a/app/src/androidTest/kotlin/org/wordpress/aztec/demo/pages/EditorPage.kt
+++ b/app/src/androidTest/kotlin/org/wordpress/aztec/demo/pages/EditorPage.kt
@@ -26,6 +26,9 @@ class EditorPage : BasePage() {
     private var editor: ViewInteraction
     private var htmlEditor: ViewInteraction
 
+    private var undoButton: ViewInteraction
+    private var redoButton: ViewInteraction
+
     private var insertMediaButton: ViewInteraction
     private var headingButton: ViewInteraction
     private var listButton: ViewInteraction
@@ -50,6 +53,9 @@ class EditorPage : BasePage() {
         editor = onView(withId(R.id.aztec))
         htmlEditor = onView(withId(R.id.source))
 
+        undoButton = onView(withId(R.id.undo))
+        redoButton = onView(withId(R.id.redo))
+
         insertMediaButton = onView(withId(R.id.format_bar_button_media))
         headingButton = onView(withId(R.id.format_bar_button_heading))
         listButton = onView(withId(R.id.format_bar_button_list))
@@ -145,6 +151,20 @@ class EditorPage : BasePage() {
         label("Chose device photos")
     }
 
+    fun undoChange(): EditorPage {
+        undoButton.perform(Actions.invokeClick())
+        label("Performed undo")
+
+        return this
+    }
+
+    fun redoChange(): EditorPage {
+        redoButton.perform(Actions.invokeClick())
+        label("Performed redo")
+
+        return this
+    }
+
     fun makeHeader(style: HeadingStyle): EditorPage {
         headingButton.perform(betterScrollTo(), Actions.invokeClick())
         label("Choosing heading style")
@@ -276,7 +296,7 @@ class EditorPage : BasePage() {
     }
 
     fun verifyHTML(expected: String): EditorPage {
-        htmlEditor.check(matches(withText(expected)))
+        htmlEditor.check(matches(Matchers.withStrippedText(expected)))
         label("Verified expected editor contents")
 
         return this
diff --git a/app/src/androidTest/kotlin/org/wordpress/aztec/demo/tests/ImageTests.kt b/app/src/androidTest/kotlin/org/wordpress/aztec/demo/tests/ImageTests.kt
index 3bd5f899d..525ed0d8d 100644
--- a/app/src/androidTest/kotlin/org/wordpress/aztec/demo/tests/ImageTests.kt
+++ b/app/src/androidTest/kotlin/org/wordpress/aztec/demo/tests/ImageTests.kt
@@ -24,8 +24,28 @@ class ImageTests : BaseTest() {
     @JvmField
     val mActivityIntentsTestRule = IntentsTestRule<MainActivity>(MainActivity::class.java)
 
+    // Simple photo test, also tests the issue described in
+    // https://github.com/wordpress-mobile/AztecEditor-Android/issues/306
     @Test
     fun testAddPhoto() {
+        val regex = Regex("<img src=.+>")
+
+        createImageIntentFilter()
+
+        EditorPage()
+                .tapTop()
+                .insertMedia()
+
+        // Must wait for simulated upload
+        Thread.sleep(10000)
+
+        EditorPage()
+                .toggleHtml()
+                .verifyHTML(regex)
+    }
+
+    @Test
+    fun testAddPhotoAndText() {
         var sampleText = "sample text "
         val regex = Regex(".+<img src=.+>.+")
 
@@ -67,6 +87,25 @@ class ImageTests : BaseTest() {
                 .verifyHTML(regex)
     }
 
+    // Tests the issue described in
+    // https://github.com/wordpress-mobile/AztecEditor-Android/issues/299
+    @Test
+    fun testUndoImageUpload() {
+        createImageIntentFilter()
+
+        EditorPage()
+                .tapTop()
+                .insertMedia()
+
+        // Must wait for simulated upload to start
+        Thread.sleep(1000)
+
+        EditorPage()
+                .undoChange()
+                .toggleHtml()
+                .verifyHTML("")
+    }
+
     private fun addPhotoWithHTML() {
         val imageHtml = "<img src=\"https://examplebloge.files.wordpress.com/2017/02/3def4804-d9b5-11e6-88e6-d7d8864392e0.png\">"
 
diff --git a/app/src/androidTest/kotlin/org/wordpress/aztec/demo/tests/MixedTextFormattingTests.kt b/app/src/androidTest/kotlin/org/wordpress/aztec/demo/tests/MixedTextFormattingTests.kt
index 157cbaf3e..9fcb73533 100644
--- a/app/src/androidTest/kotlin/org/wordpress/aztec/demo/tests/MixedTextFormattingTests.kt
+++ b/app/src/androidTest/kotlin/org/wordpress/aztec/demo/tests/MixedTextFormattingTests.kt
@@ -108,4 +108,104 @@ class MixedTextFormattingTests : BaseTest() {
                 .toggleHtml()
                 .verifyHTML(text)
     }
+
+    @Test
+    fun testTwoHeadings() {
+        val text = "some text"
+        val html = "<h1>$text</h1><h2>$text</h2>"
+
+        EditorPage()
+                .makeHeader(EditorPage.HeadingStyle.ONE)
+                .insertText(text)
+                .insertText("\n")
+                .makeHeader(EditorPage.HeadingStyle.TWO)
+                .insertText(text)
+                .toggleHtml()
+                .verifyHTML(html)
+    }
+
+    @Test
+    fun testEndHeadingFormatting() {
+        val text = "some text"
+        val html = "<h1>$text</h1>\n$text"
+
+        EditorPage()
+                .makeHeader(EditorPage.HeadingStyle.ONE)
+                .insertText(text)
+                .insertText("\n")
+                .insertText(text)
+                .toggleHtml()
+                .verifyHTML(html)
+    }
+
+    @Test
+    fun testEndQuoteFormatting() {
+        val text = "some text"
+        val html = "<blockquote>$text</blockquote>\n$text"
+
+        EditorPage()
+                .toggleQuote()
+                .insertText(text)
+                .insertText("\n\n")
+                .insertText(text)
+                .toggleHtml()
+                .verifyHTML(html)
+    }
+
+    @Test
+    fun testRemoveQuoteFormatting() {
+        val text = "some text"
+        val html = "<blockquote>$text</blockquote>\n$text"
+
+        EditorPage()
+                .toggleQuote()
+                .insertText(text)
+                .insertText("\n")
+                .insertText(text)
+                .toggleQuote()
+                .toggleHtml()
+                .verifyHTML(html)
+    }
+
+    @Test
+    fun testQuotedListFormatting() {
+        val text = "some text\nsome text\nsome text"
+        val html = "<blockquote><ul><li>some text</li><li>some text</li><li>some text</li></ul></blockquote>"
+
+        EditorPage()
+                .toggleQuote()
+                .makeList(EditorPage.ListStyle.UNORDERED)
+                .insertText(text)
+                .toggleHtml()
+                .verifyHTML(html)
+    }
+
+    @Test
+    fun testQuotedListRemoveListFormatting() {
+        val text = "some text\nsome text\nsome text"
+        val html = "<blockquote><ul><li>some text</li><li>some text</li></ul>\nsome text</blockquote>"
+
+        EditorPage()
+                .toggleQuote()
+                .makeList(EditorPage.ListStyle.UNORDERED)
+                .insertText(text)
+                .makeList(EditorPage.ListStyle.UNORDERED)
+                .toggleHtml()
+                .verifyHTML(html)
+    }
+
+    @Test
+    fun testListwithQuoteFormatting() {
+        val text1 = "some text\nsome text\nsome text\n"
+        val text2 = "some text"
+        val html = "<ul><li>some text</li><li>some text</li><li>some text</li><li><blockquote>some text</blockquote></li></ul>"
+
+        EditorPage()
+                .makeList(EditorPage.ListStyle.UNORDERED)
+                .insertText(text1)
+                .toggleQuote()
+                .insertText(text2)
+                .toggleHtml()
+                .verifyHTML(html)
+    }
 }
diff --git a/app/src/androidTest/kotlin/org/wordpress/aztec/demo/tests/SimpleTextFormattingTests.kt b/app/src/androidTest/kotlin/org/wordpress/aztec/demo/tests/SimpleTextFormattingTests.kt
index 92df6d871..06310e3f0 100644
--- a/app/src/androidTest/kotlin/org/wordpress/aztec/demo/tests/SimpleTextFormattingTests.kt
+++ b/app/src/androidTest/kotlin/org/wordpress/aztec/demo/tests/SimpleTextFormattingTests.kt
@@ -88,7 +88,7 @@ class SimpleTextFormattingTests : BaseTest() {
     fun testSimpleUnorderedListFormatting() {
         val text1 = "some\n"
         val text2 = "text"
-        val html = "$text1<ul>\n\t<li>$text2</li>\n</ul>"
+        val html = "$text1<ul><li>$text2</li></ul>"
 
         EditorPage()
                 .insertText(text1)
@@ -102,7 +102,7 @@ class SimpleTextFormattingTests : BaseTest() {
     fun testSimpleOrderedListFormatting() {
         val text1 = "some\n"
         val text2 = "text"
-        val html = "$text1<ol>\n\t<li>$text2</li>\n</ol>"
+        val html = "$text1<ol><li>$text2</li></ol>"
 
         EditorPage()
                 .insertText(text1)
@@ -306,6 +306,29 @@ class SimpleTextFormattingTests : BaseTest() {
                 .verifyHTML(expected2)
     }
 
+    @Test
+    fun testRemoveListFormatting() {
+
+        val text = "some text\nsome text\nsome text"
+        val expected1 = "<ul><li>some text</li><li>some text</li><li>some text</li></ul>"
+        val expected2 = "<ul><li>some text</li><li>some text</li></ul>\nsome text"
+
+        EditorPage()
+                .makeList(EditorPage.ListStyle.UNORDERED)
+                .insertText(text)
+                .toggleHtml()
+                .verifyHTML(expected1)
+                .toggleHtml()
+                .makeList(EditorPage.ListStyle.UNORDERED)
+                .toggleHtml()
+                .verifyHTML(expected2)
+                .toggleHtml()
+                .selectAllText()
+                .makeList(EditorPage.ListStyle.UNORDERED)
+                .toggleHtml()
+                .verifyHTML(text)
+    }
+
     // Test reproducing the issue described in
     // https://github.com/wordpress-mobile/AztecEditor-Android/pull/466#issuecomment-322404363
     @Test