diff --git a/Userland/DevTools/HackStudio/Debugger/Debugger.cpp b/Userland/DevTools/HackStudio/Debugger/Debugger.cpp
index 55bc4faef3..7f8ef8eada 100644
--- a/Userland/DevTools/HackStudio/Debugger/Debugger.cpp
+++ b/Userland/DevTools/HackStudio/Debugger/Debugger.cpp
@@ -70,9 +70,9 @@ void Debugger::on_breakpoint_change(const String& file, size_t line, BreakpointC
     auto position = create_source_position(file, line);
 
     if (change_type == BreakpointChange::Added) {
-        Debugger::the().m_breakpoints.append(position);
+        m_breakpoints.append(position);
     } else {
-        Debugger::the().m_breakpoints.remove_all_matching([&](Debug::DebugInfo::SourcePosition val) { return val == position; });
+        m_breakpoints.remove_all_matching([&](const Debug::DebugInfo::SourcePosition& val) { return val == position; });
     }
 
     auto session = Debugger::the().session();
@@ -99,9 +99,9 @@ void Debugger::on_breakpoint_change(const String& file, size_t line, BreakpointC
 
 Debug::DebugInfo::SourcePosition Debugger::create_source_position(const String& file, size_t line)
 {
-    if (!file.starts_with('/') && !file.starts_with("./"))
-        return { String::formatted("./{}", file), line + 1 };
-    return { file, line + 1 };
+    if (file.starts_with("/"))
+        return { file, line + 1 };
+    return { LexicalPath::canonicalized_path(String::formatted("{}/{}", m_source_root, file)), line + 1 };
 }
 
 int Debugger::start_static()
diff --git a/Userland/DevTools/HackStudio/Debugger/Debugger.h b/Userland/DevTools/HackStudio/Debugger/Debugger.h
index 0d2371f86e..1228a1ac0e 100644
--- a/Userland/DevTools/HackStudio/Debugger/Debugger.h
+++ b/Userland/DevTools/HackStudio/Debugger/Debugger.h
@@ -28,6 +28,7 @@
 
 #include "BreakpointCallback.h"
 #include <AK/Function.h>
+#include <AK/LexicalPath.h>
 #include <AK/Vector.h>
 #include <LibDebug/DebugSession.h>
 #include <LibThread/Lock.h>
@@ -52,9 +53,10 @@ public:
 
     static bool is_initialized();
 
-    static void on_breakpoint_change(const String& file, size_t line, BreakpointChange change_type);
+    void on_breakpoint_change(const String& file, size_t line, BreakpointChange change_type);
 
     void set_executable_path(const String& path) { m_executable_path = path; }
+    void set_source_root(const String& source_root) { m_source_root = source_root; }
 
     Debug::DebugSession* session() { return m_debug_session.ptr(); }
 
@@ -108,7 +110,7 @@ private:
         Function<void()> on_continue_callback,
         Function<void()> on_exit_callback);
 
-    static Debug::DebugInfo::SourcePosition create_source_position(const String& file, size_t line);
+    Debug::DebugInfo::SourcePosition create_source_position(const String& file, size_t line);
 
     void start();
     int debugger_loop();
diff --git a/Userland/DevTools/HackStudio/Editor.cpp b/Userland/DevTools/HackStudio/Editor.cpp
index e4b1c8bf74..6cdbca9cfa 100644
--- a/Userland/DevTools/HackStudio/Editor.cpp
+++ b/Userland/DevTools/HackStudio/Editor.cpp
@@ -272,10 +272,10 @@ void Editor::mousedown_event(GUI::MouseEvent& event)
     if (event.button() == GUI::MouseButton::Left && event.position().x() < ruler_line_rect.width()) {
         if (!breakpoint_lines().contains_slow(text_position.line())) {
             breakpoint_lines().append(text_position.line());
-            Debugger::on_breakpoint_change(wrapper().filename_label().text(), text_position.line(), BreakpointChange::Added);
+            Debugger::the().on_breakpoint_change(wrapper().filename_label().text(), text_position.line(), BreakpointChange::Added);
         } else {
             breakpoint_lines().remove_first_matching([&](size_t line) { return line == text_position.line(); });
-            Debugger::on_breakpoint_change(wrapper().filename_label().text(), text_position.line(), BreakpointChange::Removed);
+            Debugger::the().on_breakpoint_change(wrapper().filename_label().text(), text_position.line(), BreakpointChange::Removed);
         }
     }
 
diff --git a/Userland/DevTools/HackStudio/HackStudioWidget.cpp b/Userland/DevTools/HackStudio/HackStudioWidget.cpp
index 9529edb9d8..5d64f8a5d8 100644
--- a/Userland/DevTools/HackStudio/HackStudioWidget.cpp
+++ b/Userland/DevTools/HackStudio/HackStudioWidget.cpp
@@ -198,7 +198,9 @@ void HackStudioWidget::open_project(const String& root_path)
         m_project_tree_view->update();
     }
     if (Debugger::is_initialized()) {
-        Debugger::the().reset_breakpoints();
+        auto& debugger = Debugger::the();
+        debugger.reset_breakpoints();
+        debugger.set_source_root(m_project->root_path());
     }
 }