diff --git a/platformio/commands/debug.py b/platformio/commands/debug.py
index 7abb1976..44e3302a 100644
--- a/platformio/commands/debug.py
+++ b/platformio/commands/debug.py
@@ -120,8 +120,9 @@ def cli(ctx, project_dir, project_conf, environment, verbose, interface, __unpro
         rebuild_prog = helpers.is_prog_obsolete(
             debug_config.program_path
         ) or not helpers.has_debug_symbols(debug_config.program_path)
-    else:
-        rebuild_prog = not os.path.isfile(debug_config.program_path)
+
+    if not (debug_config.program_path and os.path.isfile(debug_config.program_path)):
+        rebuild_prog = True
 
     if preload or (not rebuild_prog and load_mode != "always"):
         # don't load firmware through debug server
diff --git a/platformio/debug/config/base.py b/platformio/debug/config/base.py
index 4143117d..13fd804f 100644
--- a/platformio/debug/config/base.py
+++ b/platformio/debug/config/base.py
@@ -88,7 +88,12 @@ class DebugConfigBase:  # pylint: disable=too-many-instance-attributes
 
     @property
     def init_break(self):
-        result = self.env_options.get("debug_init_break")
+        missed = object()
+        result = self.env_options.get("debug_init_break", missed)
+        if result != missed:
+            return result
+        else:
+            result = None
         if not result:
             result = self.tool_settings.get("init_break")
         return result or ProjectOptions["env.debug_init_break"].default
@@ -196,13 +201,14 @@ class DebugConfigBase:  # pylint: disable=too-many-instance-attributes
             raise NotImplementedError
 
     def reveal_patterns(self, source, recursive=True):
+        program_path = self.program_path or ""
         patterns = {
             "PLATFORMIO_CORE_DIR": get_project_core_dir(),
             "PYTHONEXE": proc.get_pythonexe_path(),
             "PROJECT_DIR": self.project_config.path,
-            "PROG_PATH": self.program_path,
-            "PROG_DIR": os.path.dirname(self.program_path),
-            "PROG_NAME": os.path.basename(os.path.splitext(self.program_path)[0]),
+            "PROG_PATH": program_path,
+            "PROG_DIR": os.path.dirname(program_path),
+            "PROG_NAME": os.path.basename(os.path.splitext(program_path)[0]),
             "DEBUG_PORT": self.port,
             "UPLOAD_PROTOCOL": self.upload_protocol,
             "INIT_BREAK": self.init_break or "",