diff --git a/packages/react-native-aztec/android/src/main/kotlin/org/wordpress/mobile/ReactNativeAztec/EnterPressedWatcher.kt b/packages/react-native-aztec/android/src/main/kotlin/org/wordpress/mobile/ReactNativeAztec/EnterPressedWatcher.kt
index cc68aac2e17fd..097ec027fdee6 100644
--- a/packages/react-native-aztec/android/src/main/kotlin/org/wordpress/mobile/ReactNativeAztec/EnterPressedWatcher.kt
+++ b/packages/react-native-aztec/android/src/main/kotlin/org/wordpress/mobile/ReactNativeAztec/EnterPressedWatcher.kt
@@ -24,6 +24,9 @@ class EnterPressedWatcher(aztecText: AztecText, var enterDeleter: EnterDeleter)
     private var selEnd: Int = 0
     var done = false
 
+    private var gboardReplacement: CharSequence? = null
+
+
     override fun beforeTextChanged(text: CharSequence, start: Int, count: Int, after: Int) {
         val aztecText = aztecTextRef.get()
         if (aztecText?.getAztecKeyListener() != null && !aztecText.isTextChangedListenerDisabled()) {
@@ -32,6 +35,13 @@ class EnterPressedWatcher(aztecText: AztecText, var enterDeleter: EnterDeleter)
             this.start = start
             this.selStart = aztecText.selectionStart
             this.selEnd = aztecText.selectionEnd
+
+            if (selStart == selEnd && 0 < count && count < after) {
+                // possible gboard replacement detected
+                gboardReplacement = text.subSequence(start, start + count)
+            } else {
+                gboardReplacement = null
+            }
         }
     }
 
@@ -40,14 +50,25 @@ class EnterPressedWatcher(aztecText: AztecText, var enterDeleter: EnterDeleter)
         val aztecKeyListener = aztecText?.getAztecKeyListener()
         if (aztecText != null && !aztecText.isTextChangedListenerDisabled() && aztecKeyListener != null) {
             val newTextCopy = SpannableStringBuilder(text)
+
+            var gboardOffset = this.start
+            // If gboard replacement is happening, we offset the start position by the length
+            // of the gboard replacement
+            if (gboardReplacement != null) {
+                val gboardRestored = newTextCopy.subSequence(start, start + before)
+                if (gboardRestored.toString() == gboardReplacement.toString()) {
+                    gboardOffset += gboardRestored.length
+                }
+            }
+
             // if new text length is longer than original text by 1
             if (textBefore?.length == newTextCopy.length - 1) {
                 // now check that the inserted character is actually a NEWLINE
-                if (newTextCopy[this.start] == Constants.NEWLINE) {
+                if (newTextCopy[gboardOffset] == Constants.NEWLINE) {
                     done = false
                     aztecText.editableText.setSpan(EnterPressedUnderway(), 0, 0, Spanned.SPAN_USER)
                     aztecKeyListener.onEnterKey(
-                            newTextCopy.replace(this.start, this.start + 1, ""),
+                            newTextCopy.replace(gboardOffset, gboardOffset + 1, ""),
                             true,
                             selStart,
                             selEnd
@@ -61,9 +82,12 @@ class EnterPressedWatcher(aztecText: AztecText, var enterDeleter: EnterDeleter)
         aztecTextRef.get()?.editableText?.getSpans(0, 0, EnterPressedUnderway::class.java)?.forEach {
             if (!done) {
                 done = true
-                if (enterDeleter.shouldDeleteEnter())
-                    text.replace(start, start + 1, "")
+                if (enterDeleter.shouldDeleteEnter()) {
+                    var gboardOffset = start
+                    gboardReplacement?.let { replacement -> gboardOffset += replacement.length }
+                    text.replace(gboardOffset, gboardOffset + 1, "")
                 }
+            }
             aztecTextRef.get()?.editableText?.removeSpan(it)
         }
     }