diff --git a/printing/page_setup.cc b/printing/page_setup.cc
index b870323e04cc3c..ad0156eda455dc 100644
--- a/printing/page_setup.cc
+++ b/printing/page_setup.cc
@@ -19,6 +19,14 @@ PageMargins::PageMargins()
       bottom(0) {
 }
 
+void PageMargins::Rotate() {
+  int temp_right = right;
+  right = bottom;
+  bottom = left;
+  left = top;
+  top = temp_right;
+}
+
 void PageMargins::Clear() {
   header = 0;
   footer = 0;
@@ -50,6 +58,7 @@ void PageSetup::Clear() {
   content_area_.SetRect(0, 0, 0, 0);
   effective_margins_.Clear();
   text_height_ = 0;
+  forced_margins_ = false;
 }
 
 bool PageSetup::Equals(const PageSetup& rhs) const {
@@ -76,19 +85,17 @@ void PageSetup::Init(const gfx::Size& physical_size,
   printable_area_ = printable_area;
   text_height_ = text_height;
 
-  CalculateSizesWithinRect(printable_area_, text_height_);
+  SetRequestedMarginsAndCalculateSizes(requested_margins_);
 }
 
 void PageSetup::SetRequestedMargins(const PageMargins& requested_margins) {
-  requested_margins_ = requested_margins;
-  if (printable_area_.width() && printable_area_.height())
-    CalculateSizesWithinRect(printable_area_, text_height_);
+  forced_margins_ = false;
+  SetRequestedMarginsAndCalculateSizes(requested_margins);
 }
 
 void PageSetup::ForceRequestedMargins(const PageMargins& requested_margins) {
-  requested_margins_ = requested_margins;
-  if (physical_size_.width() && physical_size_.height())
-    CalculateSizesWithinRect(gfx::Rect(physical_size_), 0);
+  forced_margins_ = true;
+  SetRequestedMarginsAndCalculateSizes(requested_margins);
 }
 
 void PageSetup::FlipOrientation() {
@@ -100,10 +107,22 @@ void PageSetup::FlipOrientation() {
                                  new_y,
                                  printable_area_.height(),
                                  printable_area_.width());
+    requested_margins_.Rotate();
     Init(new_size, new_printable_area, text_height_);
   }
 }
 
+void PageSetup::SetRequestedMarginsAndCalculateSizes(
+    const PageMargins& requested_margins) {
+  requested_margins_ = requested_margins;
+  if (physical_size_.width() && physical_size_.height()) {
+    if (forced_margins_)
+      CalculateSizesWithinRect(gfx::Rect(physical_size_), 0);
+    else
+      CalculateSizesWithinRect(printable_area_, text_height_);
+  }
+}
+
 void PageSetup::CalculateSizesWithinRect(const gfx::Rect& bounds,
                                          int text_height) {
   // Calculate the effective margins. The tricky part.
diff --git a/printing/page_setup.h b/printing/page_setup.h
index 91734753acaacd..8ed342ab683a2f 100644
--- a/printing/page_setup.h
+++ b/printing/page_setup.h
@@ -15,6 +15,9 @@ class PRINTING_EXPORT PageMargins {
  public:
   PageMargins();
 
+  // Rotates the margin values in anti-clockwise direction.
+  void Rotate();
+
   void Clear();
 
   // Equality operator.
@@ -64,6 +67,10 @@ class PRINTING_EXPORT PageSetup {
   }
 
  private:
+  // Store |requested_margins_| and update page setup values.
+  void SetRequestedMarginsAndCalculateSizes(
+      const PageMargins& requested_margins);
+
   // Calculate overlay_area_, effective_margins_, and content_area_, based on
   // a constraint of |bounds| and |text_height|.
   void CalculateSizesWithinRect(const gfx::Rect& bounds, int text_height);
@@ -87,6 +94,9 @@ class PRINTING_EXPORT PageSetup {
   // Requested margins.
   PageMargins requested_margins_;
 
+  // True when |effective_margins_| respects |printable_area_| else false.
+  bool forced_margins_;
+
   // Space that must be kept free for the overlays.
   int text_height_;
 };
diff --git a/printing/page_setup_unittest.cc b/printing/page_setup_unittest.cc
index 54e436c27d28a3..00c8f2a0c9f6b0 100644
--- a/printing/page_setup_unittest.cc
+++ b/printing/page_setup_unittest.cc
@@ -190,3 +190,87 @@ TEST(PageSetupTest, OutOfRangeMargins) {
   EXPECT_EQ(setup.effective_margins().right, 0);
   EXPECT_EQ(setup.effective_margins().bottom, 0);
 }
+
+TEST(PageSetupTest, FlipOrientation) {
+  // Margins.
+  printing::PageMargins margins;
+  margins.header = 2;
+  margins.footer = 3;
+  margins.left = 4;
+  margins.top = 14;
+  margins.right = 6;
+  margins.bottom = 7;
+  int kTextHeight = 5;
+
+  // Page description.
+  gfx::Size page_size(100, 70);
+  gfx::Rect printable_area(8, 9, 92, 50);
+
+  // Make the calculations.
+  printing::PageSetup setup;
+  setup.SetRequestedMargins(margins);
+  setup.Init(page_size, printable_area, kTextHeight);
+
+  gfx::Rect overlay_area(8, 9, 86, 50);
+  gfx::Rect content_area(8, 14, 86, 40);
+
+  EXPECT_EQ(page_size, setup.physical_size());
+  EXPECT_EQ(overlay_area, setup.overlay_area());
+  EXPECT_EQ(content_area, setup.content_area());
+
+  EXPECT_EQ(setup.effective_margins().left, 8);
+  EXPECT_EQ(setup.effective_margins().top, 14);
+  EXPECT_EQ(setup.effective_margins().right, 6);
+  EXPECT_EQ(setup.effective_margins().bottom, 16);
+
+  // Flip the orientation
+  setup.FlipOrientation();
+
+  // Expected values.
+  gfx::Size flipped_page_size(70, 100);
+  gfx::Rect flipped_printable_area(9, 0, 50, 92);
+  gfx::Rect flipped_overlay_area(14, 2, 45, 90);
+  gfx::Rect flipped_content_area(14, 7, 45, 80);
+
+  // Test values.
+  EXPECT_EQ(flipped_page_size, setup.physical_size());
+  EXPECT_EQ(flipped_overlay_area, setup.overlay_area()) << " " <<
+      flipped_page_size.ToString() << " " << flipped_printable_area.ToString();
+  EXPECT_EQ(flipped_content_area, setup.content_area()) << " " <<
+      flipped_page_size.ToString() << " " << flipped_printable_area.ToString();
+  EXPECT_EQ(flipped_printable_area, setup.printable_area());
+
+  // Margin values are updated as per the flipped values.
+  EXPECT_EQ(setup.effective_margins().left, 14);
+  EXPECT_EQ(setup.effective_margins().top, 7);
+  EXPECT_EQ(setup.effective_margins().right, 11);
+  EXPECT_EQ(setup.effective_margins().bottom, 13);
+
+  // Force requested margins and flip the orientation.
+  setup.Init(page_size, printable_area, kTextHeight);
+  setup.ForceRequestedMargins(margins);
+  EXPECT_EQ(setup.effective_margins().left, 4);
+  EXPECT_EQ(setup.effective_margins().top, 14);
+  EXPECT_EQ(setup.effective_margins().right, 6);
+  EXPECT_EQ(setup.effective_margins().bottom, 7);
+
+  // Flip the orientation
+  setup.FlipOrientation();
+
+  // Expected values.
+  gfx::Rect new_printable_area(9, 0, 50, 92);
+  gfx::Rect new_overlay_area(14, 2, 49, 95);
+  gfx::Rect new_content_area(14, 6, 49, 90);
+
+  // Test values.
+  EXPECT_EQ(flipped_page_size, setup.physical_size());
+  EXPECT_EQ(new_overlay_area, setup.overlay_area());
+  EXPECT_EQ(new_content_area, setup.content_area());
+  EXPECT_EQ(new_printable_area, setup.printable_area());
+
+  // Margins values are changed respectively.
+  EXPECT_EQ(setup.effective_margins().left,14);
+  EXPECT_EQ(setup.effective_margins().top, 6);
+  EXPECT_EQ(setup.effective_margins().right, 7);
+  EXPECT_EQ(setup.effective_margins().bottom, 4);
+}
diff --git a/printing/print_settings.cc b/printing/print_settings.cc
index 70ace6dcf9da36..ddf3108e229e29 100644
--- a/printing/print_settings.cc
+++ b/printing/print_settings.cc
@@ -153,9 +153,6 @@ void PrintSettings::SetPrinterPrintableArea(
     header_footer_text_height = ConvertUnit(kSettingHeaderFooterInterstice,
                                             kPointsPerInch, units_per_inch);
   }
-  page_setup_device_units_.Init(physical_size_device_units,
-                                printable_area_device_units,
-                                header_footer_text_height);
 
   PageMargins margins;
   switch (margin_type) {
@@ -211,6 +208,10 @@ void PrintSettings::SetPrinterPrintableArea(
     page_setup_device_units_.SetRequestedMargins(margins);
   else
     page_setup_device_units_.ForceRequestedMargins(margins);
+
+  page_setup_device_units_.Init(physical_size_device_units,
+                                printable_area_device_units,
+                                header_footer_text_height);
 }
 
 void PrintSettings::SetCustomMargins(