diff --git a/app/src/main/java/be/scri/helpers/DatabaseHelper.kt b/app/src/main/java/be/scri/helpers/DatabaseHelper.kt
index 10d124d8..56cb41cc 100644
--- a/app/src/main/java/be/scri/helpers/DatabaseHelper.kt
+++ b/app/src/main/java/be/scri/helpers/DatabaseHelper.kt
@@ -63,6 +63,8 @@ class DatabaseHelper(
             getRequiredData(language),
         )
 
+    fun getEmojiMaxKeywordLength(): Int = dbManagers.emojiManager.maxKeywordLength
+
     fun findCaseAnnnotationForPreposition(language: String): HashMap<String, MutableList<String>> =
         if (language != "DE" && language != "RU") {
             hashMapOf()
diff --git a/app/src/main/java/be/scri/helpers/keyboardDBHelper/EmojiDataManager.kt b/app/src/main/java/be/scri/helpers/keyboardDBHelper/EmojiDataManager.kt
index 12027361..31b0055f 100644
--- a/app/src/main/java/be/scri/helpers/keyboardDBHelper/EmojiDataManager.kt
+++ b/app/src/main/java/be/scri/helpers/keyboardDBHelper/EmojiDataManager.kt
@@ -11,6 +11,9 @@ import android.database.sqlite.SQLiteDatabase
 class EmojiDataManager(
     private val context: Context,
 ) {
+    // Track max keyword length.
+    var maxKeywordLength = 0
+
     fun getEmojiKeywords(language: String): HashMap<String, MutableList<String>> {
         val dbFile = context.getDatabasePath("${language}LanguageData.sqlite")
         return processEmojiKeywords(dbFile.path)
@@ -18,10 +21,17 @@ class EmojiDataManager(
 
     private fun processEmojiKeywords(dbPath: String): HashMap<String, MutableList<String>> {
         val hashMap = HashMap<String, MutableList<String>>()
-        val db = SQLiteDatabase.openDatabase(dbPath, null, SQLiteDatabase.OPEN_READONLY)
 
-        db.use { database ->
-            database.rawQuery("SELECT * FROM emoji_keywords", null).use { cursor ->
+        SQLiteDatabase.openDatabase(dbPath, null, SQLiteDatabase.OPEN_READONLY).use { db ->
+            // Get max keyword length.
+            db.rawQuery("SELECT MAX(LENGTH(word)) FROM emoji_keywords", null).use { cursor ->
+                if (cursor.moveToFirst()) {
+                    maxKeywordLength = cursor.getInt(0)
+                }
+            }
+
+            // Keyword processing.
+            db.rawQuery("SELECT * FROM emoji_keywords", null).use { cursor ->
                 processEmojiCursor(cursor, hashMap)
             }
         }
diff --git a/app/src/main/java/be/scri/services/GeneralKeyboardIME.kt b/app/src/main/java/be/scri/services/GeneralKeyboardIME.kt
index 9de7836f..bc630f78 100644
--- a/app/src/main/java/be/scri/services/GeneralKeyboardIME.kt
+++ b/app/src/main/java/be/scri/services/GeneralKeyboardIME.kt
@@ -93,6 +93,7 @@ abstract class GeneralKeyboardIME(
 
     private lateinit var dbHelper: DatabaseHelper
     lateinit var emojiKeywords: HashMap<String, MutableList<String>>
+    var emojiMaxKeywordLength: Int = 0
     lateinit var nounKeywords: HashMap<String, List<String>>
     lateinit var pluralWords: List<String>
     lateinit var caseAnnotation: HashMap<String, MutableList<String>>
@@ -295,6 +296,7 @@ abstract class GeneralKeyboardIME(
         dbHelper = DatabaseHelper(this)
         dbHelper.loadDatabase(languageAlias)
         emojiKeywords = dbHelper.getEmojiKeywords(languageAlias)
+        emojiMaxKeywordLength = dbHelper.getEmojiMaxKeywordLength()
         pluralWords = dbHelper.checkIfWordIsPlural(languageAlias)!!
         nounKeywords = dbHelper.findGenderOfWord(languageAlias)
 
@@ -1229,12 +1231,52 @@ abstract class GeneralKeyboardIME(
 
     /**
      * Inserts the specified emoji into the current input field.
+     * Replaces the last word if there's no trailing space.
      *
      * @param emoji The emoji character to be inserted.
      */
     private fun insertEmoji(emoji: String) {
         val inputConnection = currentInputConnection ?: return
-        inputConnection.commitText(emoji, 1)
+        val maxLookBack = emojiMaxKeywordLength.coerceAtLeast(1)
+
+        inputConnection.beginBatchEdit()
+        try {
+            val previousText = inputConnection.getTextBeforeCursor(maxLookBack, 0)?.toString() ?: ""
+
+            // Find last word boundary efficiently
+            val lastSpaceIndex = previousText.lastIndexOf(' ')
+            val hasSpace = lastSpaceIndex != -1
+
+            when {
+                // Case 1: Ends with space or empty
+                previousText.isEmpty() || hasSpace && lastSpaceIndex == previousText.length - 1 -> {
+                    inputConnection.commitText(emoji, 1)
+                }
+
+                // Case 2: Has previous word
+                hasSpace -> {
+                    val lastWord = previousText.substring(lastSpaceIndex + 1)
+                    if (emojiKeywords.containsKey(lastWord.lowercase())) {
+                        inputConnection.deleteSurroundingText(lastWord.length, 0)
+                        inputConnection.commitText(emoji, 1)
+                    } else {
+                        inputConnection.commitText(emoji, 1)
+                    }
+                }
+
+                // Case 3: Entire text is the word
+                else -> {
+                    if (emojiKeywords.containsKey(previousText.lowercase())) {
+                        inputConnection.deleteSurroundingText(previousText.length, 0)
+                        inputConnection.commitText(emoji, 1)
+                    } else {
+                        inputConnection.commitText(emoji, 1)
+                    }
+                }
+            }
+        } finally {
+            inputConnection.endBatchEdit()
+        }
     }
 
     /**