diff --git a/src/develop/develop.h b/src/develop/develop.h
index 9218201f466d..8e4836c9eb4b 100644
--- a/src/develop/develop.h
+++ b/src/develop/develop.h
@@ -289,11 +289,16 @@ typedef struct dt_develop_t
 
   dt_dev_chroma_t chroma;
 
-  // for exposing the crop
+  // for exposing and handling the crop
   struct
   {
     // set by dt_dev_pixelpipe_synch() if an enabled crop module is included in history
     struct dt_iop_module_t *exposer;
+
+    // proxy to change crop settings via flip module
+    struct dt_iop_module_t *flip_handler;
+    void (*flip_callback)(struct dt_iop_module_t *crop,
+                          const dt_image_orientation_t flipmode);
   } cropping;
 
   // for the overexposure indicator
diff --git a/src/iop/crop.c b/src/iop/crop.c
index 07e065c8a32a..231908faf449 100644
--- a/src/iop/crop.c
+++ b/src/iop/crop.c
@@ -236,8 +236,7 @@ static gboolean _set_max_clip(dt_iop_module_t *self)
 
   // we want to know the size of the actual buffer
   dt_dev_pixelpipe_t *fpipe = self->dev->full.pipe;
-  dt_dev_pixelpipe_iop_t *piece =
-    dt_dev_distort_get_iop_pipe(self->dev, fpipe, self);
+  const dt_dev_pixelpipe_iop_t *piece = dt_dev_distort_get_iop_pipe(self->dev, fpipe, self);
   if(!piece) return FALSE;
 
   const float wp = piece->buf_out.width;
@@ -536,8 +535,7 @@ static float _aspect_ratio_get(dt_iop_module_t *self, GtkWidget *combo)
   }
 
   // we want to know the size of the actual buffer
-  dt_dev_pixelpipe_iop_t *piece =
-    dt_dev_distort_get_iop_pipe(self->dev, self->dev->preview_pipe, self);
+  const dt_dev_pixelpipe_iop_t *piece = dt_dev_distort_get_iop_pipe(self->dev, self->dev->preview_pipe, self);
   if(!piece) return 0.0f;
 
   const int iwd = piece->buf_in.width, iht = piece->buf_in.height;
@@ -1117,6 +1115,23 @@ static gchar *_aspect_format(gchar *original,
     return g_strdup_printf("%s  %4.2f", original, (float)adim / (float)bdim);
 }
 
+static void _crop_handle_flip(dt_iop_module_t *self, const dt_image_orientation_t mode)
+{
+  dt_iop_crop_params_t *p = self ? self->params : NULL;
+  if(!p || (p->cx == 0.f && p->cy == 0.f && p->cw == 1.f && p->ch == 1.f))
+    return;
+
+  const float ocx = p->cx;
+  const float ocy = p->cy;
+  if(mode == ORIENTATION_FLIP_HORIZONTALLY)      {p->cx = 1.f-p->cw; p->cw = 1.f-ocx;}
+  else if(mode == ORIENTATION_FLIP_VERTICALLY)   {p->cy = 1.f-p->ch; p->ch = 1.f-ocy;}
+  else if(mode == ORIENTATION_ROTATE_CW_90_DEG)  {p->cx = 1.f-p->ch; p->ch = p->cw;     p->cw = 1.f-p->cy; p->cy = ocx;}
+  else if(mode == ORIENTATION_ROTATE_CCW_90_DEG) {p->cx = p->cy;     p->cy = 1.f-p->cw; p->cw = p->ch;     p->ch = 1.f-ocx;}
+
+  dt_iop_gui_update(self);
+  dt_dev_add_history_item(darktable.develop, self, self->enabled);
+}
+
 void gui_init(dt_iop_module_t *self)
 {
   dt_iop_crop_gui_data_t *g = IOP_GUI_ALLOC(crop);
@@ -1308,6 +1323,9 @@ void gui_init(dt_iop_module_t *self)
                               _("the bottom margin cannot overlap with the top margin"));
 
   self->widget = box_enabled;
+
+  darktable.develop->cropping.flip_handler = self;
+  darktable.develop->cropping.flip_callback = _crop_handle_flip;
 }
 
 static void _aspect_free(gpointer data)
diff --git a/src/iop/flip.c b/src/iop/flip.c
index 12750303dad2..6d76a931871a 100644
--- a/src/iop/flip.c
+++ b/src/iop/flip.c
@@ -431,7 +431,7 @@ void commit_params(dt_iop_module_t *self,
     d->orientation = p->orientation;
 
   if(d->orientation == ORIENTATION_NONE)
-    piece->enabled = 0;
+    piece->enabled = FALSE;
 }
 
 void init_pipe(dt_iop_module_t *self,
@@ -518,6 +518,20 @@ void reload_defaults(dt_iop_module_t *self)
   }
 }
 
+static void _crop_callback(dt_iop_module_t *self,
+                           const dt_image_orientation_t mode)
+{
+  dt_develop_t *dev = darktable.develop;
+  dt_iop_module_t *cropper = dev->cropping.flip_handler;
+
+  // FIXME: can we "compress" history here by checking for a flip/crop pair on top of history
+  // and a) drop the crop on top of history and b) compress flip in one step
+
+  dt_dev_add_history_item(dev, self, TRUE);
+  if(cropper && dev->cropping.flip_callback)
+    dev->cropping.flip_callback(cropper, mode);
+}
+
 static void do_rotate(dt_iop_module_t *self, uint32_t cw)
 {
   dt_iop_flip_params_t *p = self->params;
@@ -543,7 +557,7 @@ static void do_rotate(dt_iop_module_t *self, uint32_t cw)
   orientation ^= ORIENTATION_SWAP_XY;
 
   p->orientation = orientation;
-  dt_dev_add_history_item(darktable.develop, self, TRUE);
+  _crop_callback(self, cw ? ORIENTATION_ROTATE_CW_90_DEG : ORIENTATION_ROTATE_CCW_90_DEG);
 }
 
 static void rotate_cw(GtkWidget *widget, dt_iop_module_t *self)
@@ -569,7 +583,7 @@ static void _flip_h(GtkWidget *widget, dt_iop_module_t *self)
   else
     p->orientation = orientation ^ ORIENTATION_FLIP_HORIZONTALLY;
 
-  dt_dev_add_history_item(darktable.develop, self, TRUE);
+  _crop_callback(self, ORIENTATION_FLIP_HORIZONTALLY);
 }
 
 static void _flip_v(GtkWidget *widget, dt_iop_module_t *self)
@@ -586,7 +600,7 @@ static void _flip_v(GtkWidget *widget, dt_iop_module_t *self)
   else
     p->orientation = orientation ^ ORIENTATION_FLIP_VERTICALLY;
 
-  dt_dev_add_history_item(darktable.develop, self, TRUE);
+  _crop_callback(self, ORIENTATION_FLIP_VERTICALLY);
 }
 
 void gui_init(dt_iop_module_t *self)