diff --git a/platformio/commands/debug/helpers.py b/platformio/commands/debug/helpers.py
index 0ec7d447..4604a861 100644
--- a/platformio/commands/debug/helpers.py
+++ b/platformio/commands/debug/helpers.py
@@ -125,7 +125,8 @@ def validate_debug_options(cmd_ctx, env_options):
         server_options["executable"] = server_options["arguments"][0]
         server_options["arguments"] = server_options["arguments"][1:]
     elif "server" in tool_settings:
-        server_package = tool_settings["server"].get("package")
+        server_options = tool_settings["server"]
+        server_package = server_options.get("package")
         server_package_dir = (
             platform.get_package_dir(server_package) if server_package else None
         )
@@ -134,15 +135,17 @@ def validate_debug_options(cmd_ctx, env_options):
                 with_packages=[server_package], skip_default_package=True, silent=True
             )
             server_package_dir = platform.get_package_dir(server_package)
-        server_options = dict(
-            cwd=server_package_dir if server_package else None,
-            executable=tool_settings["server"].get("executable"),
-            arguments=[
-                a.replace("$PACKAGE_DIR", server_package_dir)
-                if server_package_dir
-                else a
-                for a in tool_settings["server"].get("arguments", [])
-            ],
+        server_options.update(
+            dict(
+                cwd=server_package_dir if server_package else None,
+                executable=server_options.get("executable"),
+                arguments=[
+                    a.replace("$PACKAGE_DIR", server_package_dir)
+                    if server_package_dir
+                    else a
+                    for a in server_options.get("arguments", [])
+                ],
+            )
         )
 
     extra_cmds = _cleanup_cmds(env_options.get("debug_extra_cmds"))
diff --git a/platformio/commands/debug/server.py b/platformio/commands/debug/server.py
index a74b1684..d50ac9d0 100644
--- a/platformio/commands/debug/server.py
+++ b/platformio/commands/debug/server.py
@@ -35,6 +35,7 @@ class DebugServer(BaseProcess):
         self._debug_port = ":3333"
         self._transport = None
         self._process_ended = False
+        self._ready = False
 
     @defer.inlineCallbacks
     def spawn(self, patterns):  # pylint: disable=too-many-branches
@@ -126,15 +127,7 @@ class DebugServer(BaseProcess):
         timeout = 10
         elapsed = 0
         delay = 1
-        ready_delay = 0.5
-        while (
-            not self._process_ended
-            and elapsed < timeout
-            and (
-                not self._last_activity
-                or not (self._last_activity < (time.time() - ready_delay))
-            )
-        ):
+        while not self._ready and not self._process_ended and elapsed < timeout:
             yield self.async_sleep(delay)
             elapsed += delay
 
@@ -151,6 +144,14 @@ class DebugServer(BaseProcess):
         super(DebugServer, self).outReceived(
             escape_gdbmi_stream("@", data) if is_gdbmi_mode() else data
         )
+        if self._ready:
+            return
+        ready_pattern = self.debug_options.get("server", {}).get("ready_pattern")
+        if ready_pattern:
+            self._ready = ready_pattern.encode() in data
+        else:
+            ready_delay = 0.5
+            self._ready = self._last_activity < (time.time() - ready_delay)
 
     def processEnded(self, reason):
         self._process_ended = True