diff --git a/Userland/DevTools/HackStudio/Debugger/Debugger.cpp b/Userland/DevTools/HackStudio/Debugger/Debugger.cpp
index 2a5a193fcec..3f22bfcea88 100644
--- a/Userland/DevTools/HackStudio/Debugger/Debugger.cpp
+++ b/Userland/DevTools/HackStudio/Debugger/Debugger.cpp
@@ -1,5 +1,6 @@
 /*
  * Copyright (c) 2020, Itamar S. <itamar8910@gmail.com>
+ * Copyright (c) 2024, Sam Atkins <atkinssj@serenityos.org>
  *
  * SPDX-License-Identifier: BSD-2-Clause
  */
@@ -48,36 +49,44 @@ Debugger::Debugger(
     pthread_cond_init(&m_ui_action_cond, nullptr);
 }
 
-void Debugger::on_breakpoint_change(ByteString const& file, size_t line, BreakpointChange change_type)
+bool Debugger::change_breakpoint(ByteString const& file, size_t line, BreakpointChange change_type)
 {
     auto position = create_source_position(file, line);
-
-    if (change_type == BreakpointChange::Added) {
-        m_breakpoints.append(position);
-    } else {
-        m_breakpoints.remove_all_matching([&](Debug::DebugInfo::SourcePosition const& val) { return val == position; });
-    }
-
     auto session = Debugger::the().session();
-    if (!session)
-        return;
+    if (session) {
+        auto address = session->get_address_from_source_position(position.file_path, position.line_number);
+        if (!address.has_value()) {
+            dbgln("Warning: couldn't get instruction address from source");
+            return false;
+        }
 
-    auto address = session->get_address_from_source_position(position.file_path, position.line_number);
-    if (!address.has_value()) {
-        dbgln("Warning: couldn't get instruction address from source");
-        // TODO: Currently, the GUI will indicate that a breakpoint was inserted/removed at this line,
-        // regardless of whether we actually succeeded to insert it. (For example a breakpoint on a comment, or an include statement).
-        // We should indicate failure via a return value from this function, and not update the breakpoint GUI if we fail.
-        return;
+        switch (change_type) {
+        case BreakpointChange::Added:
+            if (session->insert_breakpoint(address.value().address)) {
+                m_breakpoints.append(position);
+                return true;
+            }
+            break;
+        case BreakpointChange::Removed:
+            if (session->remove_breakpoint(address.value().address)) {
+                m_breakpoints.remove_all_matching([&](Debug::DebugInfo::SourcePosition const& val) { return val == position; });
+                return true;
+            }
+            break;
+        }
+        return false;
     }
 
-    if (change_type == BreakpointChange::Added) {
-        bool success = session->insert_breakpoint(address.value().address);
-        VERIFY(success);
-    } else {
-        bool success = session->remove_breakpoint(address.value().address);
-        VERIFY(success);
+    // No active session, so just modify our internal list of breakpoints
+    switch (change_type) {
+    case BreakpointChange::Added:
+        m_breakpoints.append(position);
+        return true;
+    case BreakpointChange::Removed:
+        m_breakpoints.remove_all_matching([&](Debug::DebugInfo::SourcePosition const& val) { return val == position; });
+        return true;
     }
+    VERIFY_NOT_REACHED();
 }
 
 bool Debugger::set_execution_position(ByteString const& file, size_t line)
@@ -125,6 +134,7 @@ void Debugger::start()
             bool success = m_debug_session->insert_breakpoint(address.value().address);
             VERIFY(success);
         } else {
+            // FIXME: Report the invalid breakpoint to the GUI somehow.
             dbgln("couldn't insert breakpoint");
         }
     }
diff --git a/Userland/DevTools/HackStudio/Debugger/Debugger.h b/Userland/DevTools/HackStudio/Debugger/Debugger.h
index c6b833b005c..10873a8c013 100644
--- a/Userland/DevTools/HackStudio/Debugger/Debugger.h
+++ b/Userland/DevTools/HackStudio/Debugger/Debugger.h
@@ -34,7 +34,7 @@ public:
 
     static bool is_initialized();
 
-    void on_breakpoint_change(ByteString const& file, size_t line, BreakpointChange change_type);
+    [[nodiscard]] bool change_breakpoint(ByteString const& file, size_t line, BreakpointChange change_type);
     bool set_execution_position(ByteString const& file, size_t line);
 
     void set_executable_path(ByteString const& path) { m_executable_path = path; }
diff --git a/Userland/DevTools/HackStudio/Editor.cpp b/Userland/DevTools/HackStudio/Editor.cpp
index 043ba7fa09c..14789139fb8 100644
--- a/Userland/DevTools/HackStudio/Editor.cpp
+++ b/Userland/DevTools/HackStudio/Editor.cpp
@@ -1,6 +1,7 @@
 /*
  * Copyright (c) 2018-2021, Andreas Kling <kling@serenityos.org>
  * Copyright (c) 2018-2022, the SerenityOS developers.
+ * Copyright (c) 2023-2024, Sam Atkins <atkinssj@serenityos.org>
  *
  * SPDX-License-Identifier: BSD-2-Clause
  */
@@ -774,9 +775,10 @@ void Editor::set_semantic_syntax_highlighting(bool value)
 ErrorOr<void> Editor::add_breakpoint(size_t line_number)
 {
     if (!breakpoint_lines().contains_slow(line_number)) {
-        add_gutter_indicator(m_breakpoint_indicator_id, line_number);
-        TRY(breakpoint_lines().try_append(line_number));
-        Debugger::the().on_breakpoint_change(wrapper().filename_title(), line_number, BreakpointChange::Added);
+        if (Debugger::the().change_breakpoint(wrapper().filename_title(), line_number, BreakpointChange::Added)) {
+            add_gutter_indicator(m_breakpoint_indicator_id, line_number);
+            TRY(breakpoint_lines().try_append(line_number));
+        }
     }
 
     return {};
@@ -784,9 +786,10 @@ ErrorOr<void> Editor::add_breakpoint(size_t line_number)
 
 void Editor::remove_breakpoint(size_t line_number)
 {
-    remove_gutter_indicator(m_breakpoint_indicator_id, line_number);
-    breakpoint_lines().remove_first_matching([&](size_t line) { return line == line_number; });
-    Debugger::the().on_breakpoint_change(wrapper().filename_title(), line_number, BreakpointChange::Removed);
+    if (Debugger::the().change_breakpoint(wrapper().filename_title(), line_number, BreakpointChange::Removed)) {
+        remove_gutter_indicator(m_breakpoint_indicator_id, line_number);
+        breakpoint_lines().remove_first_matching([&](size_t line) { return line == line_number; });
+    }
 }
 
 ErrorOr<void> Editor::update_git_diff_indicators()