diff --git a/core/ui/src/main/java/app/myzel394/numberhub/core/ui/common/textfield/SmartDeleteHandler.kt b/core/ui/src/main/java/app/myzel394/numberhub/core/ui/common/textfield/SmartDeleteHandler.kt
index 6876d07b..e067b459 100644
--- a/core/ui/src/main/java/app/myzel394/numberhub/core/ui/common/textfield/SmartDeleteHandler.kt
+++ b/core/ui/src/main/java/app/myzel394/numberhub/core/ui/common/textfield/SmartDeleteHandler.kt
@@ -3,12 +3,24 @@ package app.myzel394.numberhub.core.ui.common.textfield
 import androidx.compose.ui.text.TextRange
 import app.myzel394.numberhub.core.base.Token
 
-// Smartly delete tokens
+/** Smartly delete tokens
+ * @param value the current value of the text field
+ * @param selection the current selection of the text field - Assumed to be a valid selection
+ */
 data class SmartDeleteHandler(
     private val value: String,
     private val selection: TextRange,
 ) {
+    /**
+     * Calculate the range to delete based on the current selection.
+     *
+     * @return the range to delete - [Inclusive, Exclusive]
+     */
     fun calculateDeleteRange(): TextRange {
+        if (value == "") {
+            return TextRange(0, 0)
+        }
+
         if (isSelectionARange()) {
             return selection
         }
@@ -30,14 +42,20 @@ data class SmartDeleteHandler(
 
             return if (rightBracketRelativeToLeftPosition == null) {
                 // 1+2(+5|+6
-                TextRange(leftBracketPosition + 1, position)
+                TextRange((leftBracketPosition + 1).coerceAtMost(position), position)
             } else {
                 // 1+2(6)+5|+6
-                TextRange(takeNextIfIsOperator(rightBracketRelativeToLeftPosition + 1), position)
+                TextRange(
+                    takeNextIfIsOperator(rightBracketRelativeToLeftPosition + 1).coerceAtMost(
+                        position,
+                    ),
+                    position,
+                )
             }
         }
 
-        return TextRange(leftBracketPosition + 1, findClosingParen(leftBracketPosition));
+        val end = findClosingParen(leftBracketPosition)
+        return TextRange((leftBracketPosition + 1).coerceAtMost(end), end);
     }
 
     private fun takeNextIfIsOperator(position: Int): Int {
diff --git a/core/ui/src/test/java/app/myzel394/numberhub/core/ui/SmartDeleteHandlerTest.kt b/core/ui/src/test/java/app/myzel394/numberhub/core/ui/SmartDeleteHandlerTest.kt
new file mode 100644
index 00000000..12a60880
--- /dev/null
+++ b/core/ui/src/test/java/app/myzel394/numberhub/core/ui/SmartDeleteHandlerTest.kt
@@ -0,0 +1,161 @@
+package app.myzel394.numberhub.core.ui
+
+import androidx.compose.ui.text.TextRange
+import app.myzel394.numberhub.core.ui.common.textfield.SmartDeleteHandler
+import org.junit.Test
+
+class SmartDeleteHandlerTest {
+    @Test
+    fun `test simple delete`() {
+        assertDeleteRange(
+            "1+2",
+            TextRange(2, 2),
+            TextRange(0, 2),
+        )
+    }
+
+    @Test
+    fun `test brackets, position in between`() {
+        assertDeleteRange(
+            "1+(2+3)",
+            TextRange(4, 4),
+            TextRange(3, 6),
+        )
+    }
+
+    @Test
+    fun `test brackets, position at the end`() {
+        assertDeleteRange(
+            "1+(2+3)",
+            TextRange(6, 6),
+            TextRange(3, 6),
+        )
+    }
+
+    @Test
+    fun `test brackets, position at the start`() {
+        assertDeleteRange(
+            "1+(2+3)",
+            TextRange(3, 3),
+            TextRange(3, 6),
+        )
+    }
+
+    @Test
+    fun `test brackets, but position outside`() {
+        assertDeleteRange(
+            "1+(2+3)",
+            TextRange(1, 1),
+            TextRange(0, 1),
+        )
+    }
+
+    @Test
+    fun `test brackets, but cursor outside right of it`() {
+        assertDeleteRange(
+            "1+(2+3)54",
+            TextRange(8, 8),
+            TextRange(7, 8),
+        )
+    }
+
+    @Test
+    fun `test brackets, but cursor outside right of it, should go to the operator`() {
+        assertDeleteRange(
+            "1+(2+3)×54",
+            TextRange(9, 9),
+            TextRange(8, 9),
+        )
+    }
+
+    @Test
+    fun `test nested brackets, inside the nested one`() {
+        assertDeleteRange(
+            "1+(2+(3+4))",
+            TextRange(8, 8),
+            TextRange(6, 9),
+        )
+    }
+
+    @Test
+    fun `test nested brackets, inside the outside one`() {
+        assertDeleteRange(
+            "1+(2+(3+4))",
+            TextRange(4, 4),
+            TextRange(3, 10),
+        )
+    }
+
+    @Test
+    fun `test nested empty brackets`() {
+        assertDeleteRange(
+            "1+(2+())",
+            TextRange(4, 4),
+            TextRange(3, 7),
+        )
+    }
+
+    @Test
+    fun `test pure empty nested brackets`() {
+        assertDeleteRange(
+            "1+((()))",
+            TextRange(5, 5),
+            TextRange(5, 5),
+        )
+    }
+
+    @Test
+    fun `test empty string`() {
+        assertDeleteRange(
+            "",
+            TextRange(0, 0),
+            TextRange(0, 0),
+        )
+    }
+
+    @Test
+    fun `test single character with cursor ar 0,0`() {
+        assertDeleteRange(
+            "1",
+            TextRange(0, 0),
+            TextRange(0, 0),
+        )
+    }
+
+    @Test
+    fun `test single bracket with cursor at 0,0`() {
+        assertDeleteRange(
+            "(",
+            TextRange(0, 0),
+            TextRange(0, 0),
+        )
+    }
+
+    @Test
+    fun `test nested brackets with operators`() {
+        assertDeleteRange(
+            "1+(2*(3+4))",
+            TextRange(8, 8),
+            TextRange(6, 9),
+        )
+    }
+
+    @Test
+    fun `test selection range spanning multiple tokens`() {
+        assertDeleteRange(
+            "1+(2+3)*4",
+            TextRange(2, 6),
+            TextRange(2, 6),
+        )
+    }
+
+
+    private fun assertDeleteRange(input: String, selection: TextRange, expected: TextRange) {
+        val smartDeleteHandler =
+            SmartDeleteHandler(input, selection)
+        val actual = smartDeleteHandler.calculateDeleteRange()
+        assert(expected == actual) {
+            "Expected: $expected, actual: $actual"
+        }
+    }
+}
\ No newline at end of file