diff --git a/pysnooper/tracer.py b/pysnooper/tracer.py
index b05b0f9..3245e8a 100644
--- a/pysnooper/tracer.py
+++ b/pysnooper/tracer.py
@@ -100,8 +100,11 @@ def get_source_from_frame(frame):
     return source
 
 
-def get_write_and_truncate_functions(output):
-    truncate = None
+def get_write_function(output, overwrite):
+    is_path = isinstance(output, (pycompat.PathLike, str))
+    if overwrite and not is_path:
+        raise Exception('`overwrite=True` can only be used when writing '
+                        'content to file.')
     if output is None:
         def write(s):
             stderr = sys.stderr
@@ -110,14 +113,8 @@ def get_write_and_truncate_functions(output):
             except UnicodeEncodeError:
                 # God damn Python 2
                 stderr.write(utils.shitcode(s))
-    elif isinstance(output, (pycompat.PathLike, str)):
-        def write(s):
-            with open(six.text_type(output), 'a') as output_file:
-                output_file.write(s)
-
-        def truncate():
-            with open(six.text_type(output), 'w'):
-                pass
+    elif is_path:
+        return FileWriter(output, overwrite).write
     elif callable(output):
         write = output
     else:
@@ -125,7 +122,18 @@ def get_write_and_truncate_functions(output):
 
         def write(s):
             output.write(s)
-    return write, truncate
+    return write
+
+
+class FileWriter(object):
+    def __init__(self, path, overwrite):
+        self.path = six.text_type(path)
+        self.overwrite = overwrite
+
+    def write(self, s):
+        with open(self.path, 'w' if self.overwrite else 'a') as output_file:
+            output_file.write(s)
+        self.overwrite = False
 
 
 thread_global = threading.local()
@@ -180,11 +188,7 @@ class Tracer:
             overwrite=False,
             thread_info=False,
     ):
-        self._write, self.truncate = get_write_and_truncate_functions(output)
-
-        if self.truncate is None and overwrite:
-            raise Exception("`overwrite=True` can only be used when writing "
-                            "content to file.")
+        self._write = get_write_function(output, overwrite)
 
         self.watch = [
             v if isinstance(v, BaseVariable) else CommonVariable(v)
@@ -196,8 +200,6 @@ class Tracer:
         self.frame_to_local_reprs = {}
         self.depth = depth
         self.prefix = prefix
-        self.overwrite = overwrite
-        self._did_overwrite = False
         self.thread_info = thread_info
         self.thread_info_padding = 0
         assert self.depth >= 1
@@ -237,9 +239,6 @@ class Tracer:
             return simple_wrapper
 
     def write(self, s):
-        if self.overwrite and not self._did_overwrite:
-            self.truncate()
-            self._did_overwrite = True
         s = u'{self.prefix}{s}\n'.format(**locals())
         self._write(s)