diff --git a/src/Debug.cc b/src/Debug.cc
index ea9c52f77e..a1e2000bea 100644
--- a/src/Debug.cc
+++ b/src/Debug.cc
@@ -721,7 +721,6 @@ static char* get_prompt(bool reset_counter = false)
 
 string get_context_description(const Stmt* stmt, const Frame* frame)
 	{
-	char buf[1024];
 	ODesc d;
 	const BroFunc* func = frame->GetFunction();
 
@@ -739,10 +738,14 @@ string get_context_description(const Stmt* stmt, const Frame* frame)
 		loc.last_line = 0;
 		}
 
-	safe_snprintf(buf, sizeof(buf), "In %s at %s:%d",
+	size_t buf_size = strlen(d.Description()) + strlen(loc.filename) + 1024;
+	char* buf = new char[buf_size];
+	safe_snprintf(buf, buf_size, "In %s at %s:%d",
 		      d.Description(), loc.filename, loc.last_line);
 
-	return string(buf);
+	string retval(buf);
+	delete [] buf;
+	return retval;
 	}
 
 int dbg_handle_debug_input()
@@ -924,6 +927,8 @@ bool post_execute_stmt(Stmt* stmt, Frame* f, Val* result, stmt_flow_type* flow)
 // Evaluates the given expression in the context of the currently selected
 // frame.  Returns the resulting value, or nil if none (or there was an error).
 Expr* g_curr_debug_expr = 0;
+const char* g_curr_debug_error = 0;
+bool in_debug = false;
 
 // ### fix this hardwired access to external variables etc.
 struct yy_buffer_state;
@@ -969,6 +974,10 @@ Val* dbg_eval_expr(const char* expr)
 	Val* result = 0;
 	if ( yyparse() )
 		{
+		if ( g_curr_debug_error )
+			debug_msg("Parsing expression '%s' failed: %s\n", expr, g_curr_debug_error);
+		else
+			debug_msg("Parsing expression '%s' failed\n", expr);
 		if ( g_curr_debug_expr )
 			{
 			delete g_curr_debug_expr;
@@ -983,6 +992,9 @@ Val* dbg_eval_expr(const char* expr)
 
 	delete g_curr_debug_expr;
 	g_curr_debug_expr = 0;
+	delete [] g_curr_debug_error;
+	g_curr_debug_error = 0;
+	in_debug = false;
 
 	return result;
 	}
diff --git a/src/DebugCmds.cc b/src/DebugCmds.cc
index 1d3b9dd220..bfb4d6ecc8 100644
--- a/src/DebugCmds.cc
+++ b/src/DebugCmds.cc
@@ -553,7 +553,8 @@ int dbg_cmd_print(DebugCmd cmd, const vector<string>& args)
 	for ( int i = 0; i < int(args.size()); ++i )
 		{
 		expr += args[i];
-		expr += " ";
+		if ( i < int(args.size()) - 1 )
+			expr += " ";
 		}
 
 	Val* val = dbg_eval_expr(expr.c_str());
@@ -566,8 +567,7 @@ int dbg_cmd_print(DebugCmd cmd, const vector<string>& args)
 		}
 	else
 		{
-		// ### Print something?
-		// debug_msg("<expression has no value>\n");
+		debug_msg("<expression has no value>\n");
 		}
 
 	return 1;
diff --git a/src/parse.y b/src/parse.y
index f78003f08b..6875f07668 100644
--- a/src/parse.y
+++ b/src/parse.y
@@ -112,13 +112,14 @@ bool is_export = false; // true if in an export {} block
  * (obviously not reentrant).
  */
 extern Expr* g_curr_debug_expr;
+extern bool in_debug;
+extern const char* g_curr_debug_error;
 
 #define YYLTYPE yyltype
 
 Expr* bro_this = 0;
 int in_init = 0;
 int in_record = 0;
-bool in_debug = false;
 bool resolving_global_ID = false;
 bool defining_global_ID = false;
 
@@ -249,7 +250,6 @@ bro:
 		TOK_DEBUG { in_debug = true; } expr
 			{
 			g_curr_debug_expr = $3;
-			in_debug = false;
 			}
 	;
 
@@ -1685,6 +1685,9 @@ int yyerror(const char msg[])
 		strcat(msgbuf, "\nDocumentation mode is enabled: "
 		       "remember to check syntax of ## style comments\n");
 
+	if ( in_debug )
+		g_curr_debug_error = copy_string(msg);
+
 	reporter->Error("%s", msgbuf);
 
 	return 0;