diff --git a/app/src/main/java/org/mozilla/fenix/library/history/HistoryComponent.kt b/app/src/main/java/org/mozilla/fenix/library/history/HistoryComponent.kt
index ac011f761b..6cb027ed06 100644
--- a/app/src/main/java/org/mozilla/fenix/library/history/HistoryComponent.kt
+++ b/app/src/main/java/org/mozilla/fenix/library/history/HistoryComponent.kt
@@ -48,6 +48,15 @@ class HistoryComponent(
                     state
                 }
             }
+            is HistoryChange.RemoveItemForRemoval -> {
+                val mode = state.mode
+                if (mode is HistoryState.Mode.Editing) {
+                    val items = mode.selectedItems.filter { it.id != change.item.id }
+                    state.copy(mode = mode.copy(selectedItems = items))
+                } else {
+                    state
+                }
+            }
         }
     }
 
@@ -69,10 +78,12 @@ sealed class HistoryAction : Action {
     data class Select(val item: HistoryItem) : HistoryAction()
     data class EnterEditMode(val item: HistoryItem) : HistoryAction()
     data class AddItemForRemoval(val item: HistoryItem) : HistoryAction()
+    data class RemoveItemForRemoval(val item: HistoryItem) : HistoryAction()
 }
 
 sealed class HistoryChange : Change {
     data class Change(val list: List<HistoryItem>) : HistoryChange()
     data class EnterEditMode(val item: HistoryItem) : HistoryChange()
     data class AddItemForRemoval(val item: HistoryItem) : HistoryChange()
+    data class RemoveItemForRemoval(val item: HistoryItem) : HistoryChange()
 }
diff --git a/app/src/main/java/org/mozilla/fenix/library/history/HistoryFragment.kt b/app/src/main/java/org/mozilla/fenix/library/history/HistoryFragment.kt
index 43e1372cbf..0e3b6a777a 100644
--- a/app/src/main/java/org/mozilla/fenix/library/history/HistoryFragment.kt
+++ b/app/src/main/java/org/mozilla/fenix/library/history/HistoryFragment.kt
@@ -62,6 +62,8 @@ class HistoryFragment : Fragment(), CoroutineScope {
                         .onNext(HistoryChange.EnterEditMode(it.item))
                     is HistoryAction.AddItemForRemoval -> getManagedEmitter<HistoryChange>()
                         .onNext(HistoryChange.AddItemForRemoval(it.item))
+                    is HistoryAction.RemoveItemForRemoval -> getManagedEmitter<HistoryChange>()
+                        .onNext(HistoryChange.RemoveItemForRemoval(it.item))
                 }
             }
     }
diff --git a/app/src/main/java/org/mozilla/fenix/library/history/HistoryUIView.kt b/app/src/main/java/org/mozilla/fenix/library/history/HistoryUIView.kt
index 25370527a5..dcf4fbfebc 100644
--- a/app/src/main/java/org/mozilla/fenix/library/history/HistoryUIView.kt
+++ b/app/src/main/java/org/mozilla/fenix/library/history/HistoryUIView.kt
@@ -9,6 +9,7 @@ import android.view.LayoutInflater
 import android.view.View
 import android.view.ViewGroup
 import android.widget.CheckBox
+import android.widget.CompoundButton
 import android.widget.ImageView
 import android.widget.TextView
 import androidx.recyclerview.widget.LinearLayoutManager
@@ -56,9 +57,29 @@ private class HistoryAdapter(
         private val url = view.findViewById<TextView>(R.id.history_url)
         private var item: HistoryItem? = null
         private var mode: HistoryState.Mode = HistoryState.Mode.Normal
+        private val checkListener = object : CompoundButton.OnCheckedChangeListener {
+            override fun onCheckedChanged(buttonView: CompoundButton?, isChecked: Boolean) {
+                if (mode is HistoryState.Mode.Normal) { return }
+
+                item?.apply {
+                    val action = if (isChecked) {
+                        HistoryAction.AddItemForRemoval(this)
+                    } else {
+                        HistoryAction.RemoveItemForRemoval(this)
+                    }
+
+                    actionEmitter.onNext(action)
+                }
+            }
+        }
 
         init {
             view.setOnClickListener {
+                if (mode is HistoryState.Mode.Editing) {
+                    checkbox.isChecked = !checkbox.isChecked
+                    return@setOnClickListener
+                }
+
                 item?.apply {
                     actionEmitter.onNext(HistoryAction.Select(this))
                 }
@@ -72,11 +93,7 @@ private class HistoryAdapter(
                 true
             }
 
-            checkbox.setOnClickListener {
-                item?.apply {
-                    actionEmitter.onNext(HistoryAction.AddItemForRemoval(this))
-                }
-            }
+            checkbox.setOnCheckedChangeListener(checkListener)
         }
 
         fun bind(item: HistoryItem, mode: HistoryState.Mode) {
@@ -91,7 +108,9 @@ private class HistoryAdapter(
             favicon.visibility = if (isEditing) { View.INVISIBLE } else { View.VISIBLE }
 
             if (mode is HistoryState.Mode.Editing) {
+                checkbox.setOnCheckedChangeListener(null)
                 checkbox.isChecked = mode.selectedItems.contains(item)
+                checkbox.setOnCheckedChangeListener(checkListener)
             }
         }