diff --git a/trains/backend_interface/metrics/reporter.py b/trains/backend_interface/metrics/reporter.py
index ea5a172b..04e8cd56 100644
--- a/trains/backend_interface/metrics/reporter.py
+++ b/trains/backend_interface/metrics/reporter.py
@@ -55,6 +55,7 @@ class Reporter(InterfaceBase, AbstractContextManager, SetupUploadMixin, AsyncMan
         self._thread = Thread(target=self._daemon)
         self._thread.daemon = True
         self._thread.start()
+        self._max_iteration = 0
 
     def _set_storage_uri(self, value):
         value = '/'.join(x for x in (value.rstrip('/'), self._metrics.storage_key_prefix) if x)
@@ -78,6 +79,10 @@ class Reporter(InterfaceBase, AbstractContextManager, SetupUploadMixin, AsyncMan
     def async_enable(self, value):
         self._async_enable = bool(value)
 
+    @property
+    def max_iteration(self):
+        return self._max_iteration
+
     def _daemon(self):
         while not self._exit_flag:
             self._flush_event.wait(self._flush_frequency)
@@ -92,6 +97,9 @@ class Reporter(InterfaceBase, AbstractContextManager, SetupUploadMixin, AsyncMan
             self.wait_for_results()
 
     def _report(self, ev):
+        ev_iteration = ev.get_iteration()
+        if ev_iteration is not None:
+            self._max_iteration = max(self._max_iteration, ev_iteration)
         self._events.append(ev)
         if len(self._events) >= self._flush_threshold:
             self.flush()
diff --git a/trains/backend_interface/task/task.py b/trains/backend_interface/task/task.py
index 05c835ab..cdcd8e0e 100644
--- a/trains/backend_interface/task/task.py
+++ b/trains/backend_interface/task/task.py
@@ -389,7 +389,7 @@ class Task(IdObjectBase, AccessMixin, SetupUploadMixin):
         return self._reporter
 
     def _get_output_destination_suffix(self, extra_path=None):
-        return '/'.join(quote(x, safe='[]{}()$^,.; -_+-=') for x in
+        return '/'.join(quote(x, safe="'[]{}()$^,.; -_+-=") for x in
                         (self.get_project_name(), '%s.%s' % (self.name, self.data.id), extra_path) if x)
 
     def _reload(self):
diff --git a/trains/binding/frameworks/tensorflow_bind.py b/trains/binding/frameworks/tensorflow_bind.py
index ab263bb8..c68637d3 100644
--- a/trains/binding/frameworks/tensorflow_bind.py
+++ b/trains/binding/frameworks/tensorflow_bind.py
@@ -66,6 +66,15 @@ class EventTrainsWriter(object):
     _title_series_writers_lookup = {}
     _event_writers_id_to_logdir = {}
 
+    # Protect against step (iteration) reuse, for example,
+    # steps counter inside an epoch, but wrapping around when epoch ends
+    # i.e. step = 0..100 then epoch ends and again step = 0..100
+    # We store the first report per title/series combination, and if wraparound occurs
+    # we synthetically continue to increase the step/iteration based on the previous epoch counter
+    # example: _title_series_wraparound_counter[('title', 'series')] =
+    #           {'first_step':None, 'last_step':None, 'adjust_counter':0,}
+    _title_series_wraparound_counter = {}
+
     @property
     def variants(self):
         return self._variants
@@ -111,8 +120,8 @@ class EventTrainsWriter(object):
                 org_series = series
                 org_title = title
                 other_logdir = self._event_writers_id_to_logdir[event_writer_id]
-                split_logddir = self._logdir.split(os.path.sep)
-                unique_logdir = set(split_logddir) - set(other_logdir.split(os.path.sep))
+                split_logddir = self._logdir.split('/')
+                unique_logdir = set(split_logddir) - set(other_logdir.split('/'))
                 header = '/'.join(s for s in split_logddir if s in unique_logdir)
                 if logdir_header == 'series_last':
                     series = header + ': ' + series
@@ -160,6 +169,9 @@ class EventTrainsWriter(object):
         # We are the events_writer, so that's what we'll pass
         IsTensorboardInit.set_tensorboard_used()
         self._logdir = logdir or ('unknown %d' % len(self._event_writers_id_to_logdir))
+        # conform directory structure to unix
+        if os.path.sep == '\\':
+            self._logdir = self._logdir.replace('\\', '/')
         self._id = hash(self._logdir)
         self._event_writers_id_to_logdir[self._id] = self._logdir
         self.max_keep_images = max_keep_images
@@ -220,6 +232,8 @@ class EventTrainsWriter(object):
 
         title, series = self.tag_splitter(tag, num_split_parts=3, default_title='Images', logdir_header='title',
                                           auto_reduce_num_split=True)
+        step = self._fix_step_counter(title, series, step)
+
         if img_data_np.dtype != np.uint8:
             # assume scale 0-1
             img_data_np = (img_data_np * 255).astype(np.uint8)
@@ -259,6 +273,7 @@ class EventTrainsWriter(object):
         default_title = tag if not self._logger._get_tensorboard_auto_group_scalars() else 'Scalars'
         title, series = self.tag_splitter(tag, num_split_parts=1,
                                           default_title=default_title, logdir_header='series_last')
+        step = self._fix_step_counter(title, series, step)
 
         # update scalar cache
         num, value = self._scalar_report_cache.get((title, series), (0, 0))
@@ -310,6 +325,7 @@ class EventTrainsWriter(object):
         # Z-axis actual value (interpolated 'bucket')
         title, series = self.tag_splitter(tag, num_split_parts=1, default_title='Histograms',
                                           logdir_header='series')
+        step = self._fix_step_counter(title, series, step)
 
         # get histograms from cache
         hist_list, hist_iters, minmax = self._hist_report_cache.get((title, series), ([], np.array([]), None))
@@ -418,6 +434,23 @@ class EventTrainsWriter(object):
         except Exception:
             pass
 
+    def _fix_step_counter(self, title, series, step):
+        key = (title, series)
+        if key not in EventTrainsWriter._title_series_wraparound_counter:
+            EventTrainsWriter._title_series_wraparound_counter[key] = {'first_step': step, 'last_step': step,
+                                                                       'adjust_counter': 0}
+            return step
+        wraparound_counter = EventTrainsWriter._title_series_wraparound_counter[key]
+        # we decide on wrap around if the current step is less than 10% of the previous step
+        # notice since counter is int and we want to avoid rounding error, we have double check in the if
+        if step < wraparound_counter['last_step'] and step < 0.9*wraparound_counter['last_step']:
+            # adjust step base line
+            wraparound_counter['adjust_counter'] += wraparound_counter['last_step'] + (1 if step <= 0 else step)
+
+        # return adjusted step
+        wraparound_counter['last_step'] = step
+        return step + wraparound_counter['adjust_counter']
+
     def add_event(self, event, step=None, walltime=None, **kwargs):
         supported_metrics = {
             'simpleValue', 'image', 'histo', 'tensor'
diff --git a/trains/binding/matplotlib_bind.py b/trains/binding/matplotlib_bind.py
index d1507152..f4e083c6 100644
--- a/trains/binding/matplotlib_bind.py
+++ b/trains/binding/matplotlib_bind.py
@@ -21,6 +21,8 @@ class PatchedMatplotlib:
     __patched_draw_all_recursion_guard = False
     _global_plot_counter = -1
     _global_image_counter = -1
+    _global_image_counter_limit = None
+    _last_iteration_plot_titles = (-1, [])
     _current_task = None
     _support_image_plot = False
     _matplotlylib = None
@@ -125,6 +127,9 @@ class PatchedMatplotlib:
     def update_current_task(task):
         if PatchedMatplotlib.patch_matplotlib():
             PatchedMatplotlib._current_task = task
+            if PatchedMatplotlib._global_image_counter_limit is None:
+                from ..config import config
+                PatchedMatplotlib._global_image_counter_limit = config.get('metric.matplotlib_untitled_history_size', 100)
 
     @staticmethod
     def patched_imshow(*args, **kw):
@@ -310,8 +315,13 @@ class PatchedMatplotlib:
 
                 # remove borders and size, we should let the web take care of that
                 if plotly_fig:
-                    PatchedMatplotlib._global_plot_counter += 1
-                    title = plot_title or 'untitled %d' % PatchedMatplotlib._global_plot_counter
+                    last_iteration = PatchedMatplotlib._current_task.get_last_iteration()
+                    if plot_title:
+                        title = PatchedMatplotlib._enforce_unique_title_per_iteration(plot_title, last_iteration)
+                    else:
+                        PatchedMatplotlib._global_plot_counter += 1
+                        title = 'untitled %d' % PatchedMatplotlib._global_plot_counter
+
                     plotly_fig.layout.margin = {}
                     plotly_fig.layout.autosize = True
                     plotly_fig.layout.height = None
@@ -321,38 +331,59 @@ class PatchedMatplotlib:
                     if not plotly_dict.get('layout'):
                         plotly_dict['layout'] = {}
                     plotly_dict['layout']['title'] = title
-                    reporter.report_plot(title=title, series='plot', plot=plotly_dict,
-                                         iter=PatchedMatplotlib._global_plot_counter if plot_title else 0)
+                    reporter.report_plot(title=title, series='plot', plot=plotly_dict, iter=last_iteration)
                 else:
                     logger = PatchedMatplotlib._current_task.get_logger()
 
                     # this is actually a failed plot, we should put it under plots:
                     # currently disabled
                     if force_save_as_image or not PatchedMatplotlib._support_image_plot:
+                        last_iteration = PatchedMatplotlib._current_task.get_last_iteration()
                         # send the plot as image
-                        PatchedMatplotlib._global_image_counter += 1
-                        title = plot_title or 'untitled %d' % PatchedMatplotlib._global_image_counter
+                        if plot_title:
+                            title = PatchedMatplotlib._enforce_unique_title_per_iteration(plot_title, last_iteration)
+                        else:
+                            PatchedMatplotlib._global_image_counter += 1
+                            title = 'untitled %d' % (PatchedMatplotlib._global_image_counter %
+                                                     PatchedMatplotlib._global_image_counter_limit)
 
                         logger.report_image(title=title, series='plot image', local_path=image,
-                                            delete_after_upload=True,
-                                            iteration=PatchedMatplotlib._global_image_counter
-                                            if plot_title else 0)
+                                            delete_after_upload=True, iteration=last_iteration)
                     else:
                         # send the plot as plotly with embedded image
-                        PatchedMatplotlib._global_plot_counter += 1
-                        title = plot_title or 'untitled %d' % PatchedMatplotlib._global_plot_counter
+                        last_iteration = PatchedMatplotlib._current_task.get_last_iteration()
+                        if plot_title:
+                            title = PatchedMatplotlib._enforce_unique_title_per_iteration(plot_title, last_iteration)
+                        else:
+                            PatchedMatplotlib._global_plot_counter += 1
+                            title = 'untitled %d' % (PatchedMatplotlib._global_plot_counter %
+                                                     PatchedMatplotlib._global_image_counter_limit)
 
                         logger._report_image_plot_and_upload(title=title, series='plot image', path=image,
-                                                             delete_after_upload=True,
-                                                             iteration=PatchedMatplotlib._global_plot_counter
-                                                             if plot_title else 0)
-
+                                                             delete_after_upload=True, iteration=last_iteration)
         except Exception:
             # plotly failed
             pass
 
         return
 
+    @staticmethod
+    def _enforce_unique_title_per_iteration(title, last_iteration):
+        if last_iteration != PatchedMatplotlib._last_iteration_plot_titles[0]:
+            PatchedMatplotlib._last_iteration_plot_titles = (last_iteration, [title])
+        elif title not in PatchedMatplotlib._last_iteration_plot_titles[1]:
+            PatchedMatplotlib._last_iteration_plot_titles[1].append(title)
+        else:
+            base_title = title
+            counter = 1
+            while title in PatchedMatplotlib._last_iteration_plot_titles[1]:
+                # we already used this title in this iteration, we should change the title
+                title = base_title + ' %d' % counter
+                counter += 1
+            # store the new title
+            PatchedMatplotlib._last_iteration_plot_titles[1].append(title)
+        return title
+
     @staticmethod
     def _get_output_figures(stored_figure, all_figures):
         try:
diff --git a/trains/config/default/sdk.conf b/trains/config/default/sdk.conf
index 96ddf0b4..d181c4e3 100644
--- a/trains/config/default/sdk.conf
+++ b/trains/config/default/sdk.conf
@@ -21,6 +21,11 @@
         # X files are stored in the upload destination for each metric/variant combination.
         file_history_size: 100
 
+        # Max history size for matplotlib imshow files per plot title.
+        # File names for the uploaded images will be recycled in such a way that no more than
+        # X images are stored in the upload destination for each matplotlib plot title.
+        matplotlib_untitled_history_size: 100
+
         # Settings for generated debug images
         images {
             format: JPEG