diff --git a/pwnlib/data/templates/pwnup.mako b/pwnlib/data/templates/pwnup.mako
index 81307d12b..4e85cd88e 100644
--- a/pwnlib/data/templates/pwnup.mako
+++ b/pwnlib/data/templates/pwnup.mako
@@ -132,9 +132,9 @@ def start(argv=[], *a, **kw):
 gdbscript = '''
 %if ctx.binary:
   %if 'main' in ctx.binary.symbols:
-break *0x{exe.symbols.main:x}
-  %else:
-break *0x{exe.entry:x}
+tbreak main
+  %elif 'DYN' != ctx.binary.elftype:
+tbreak *0x{exe.entry:x}
   %endif
 %endif
 continue
diff --git a/pwnlib/gdb.py b/pwnlib/gdb.py
index 5bd866a58..b0a15b364 100644
--- a/pwnlib/gdb.py
+++ b/pwnlib/gdb.py
@@ -464,9 +464,9 @@ def debug(args, gdbscript=None, exe=None, ssh=None, env=None, sysroot=None, **kw
 
     # gdbserver outputs a message when a client connects
     garbage = gdbserver.recvline(timeout=1)
-
-    if "Remote debugging from host" not in garbage:
-        gdbserver.unrecv(garbage)
+    
+    # Some versions of gdbserver output an additional message
+    garbage2 = gdbserver.recvline_startswith("Remote debugging from host ", timeout=1)
 
     return gdbserver