diff --git a/src/AddIns/Debugger/Debugger.AddIn/Service/WindowsDebugger.cs b/src/AddIns/Debugger/Debugger.AddIn/Service/WindowsDebugger.cs
index cf22243d57..584dae0642 100644
--- a/src/AddIns/Debugger/Debugger.AddIn/Service/WindowsDebugger.cs
+++ b/src/AddIns/Debugger/Debugger.AddIn/Service/WindowsDebugger.cs
@@ -201,6 +201,9 @@ namespace ICSharpCode.SharpDevelop.Services
 					} else {
 						throw;
 					}
+				} finally {
+					// starting a process by "stepping into main" should only break once and not always.
+					BreakAtBeginning = false;
 				}
 			}
 		}