Try and use groups instead

IPython/lib/pretty.py

@@ -196,11 +196,7 b' class PrettyPrinter(_PrettyPrinterBase):'
         self.group_queue = GroupQueue(root_group)
         self.indentation = 0
 
-    def _break_outer_groups(self):
-        while self.max_width < self.output_width + self.buffer_width:
-            group = self.group_queue.deq()
-            if not group:
-                return
+    def _break_one_group(self, group):
             while group.breakables:
                 x = self.buffer.popleft()
                 self.output_width = x.output(self.output, self.output_width)
@@ -210,6 +206,13 b' class PrettyPrinter(_PrettyPrinterBase):'
                 self.output_width = x.output(self.output, self.output_width)
                 self.buffer_width -= x.width
 
+    def _break_outer_groups(self, force=):
+        while self.max_width < self.output_width + self.buffer_width:
+            group = self.group_queue.deq()
+            if not group:
+                return
+            self._break_one_group(group)
+
     def text(self, obj):
         """Add literal text to the output."""
         width = len(obj)
@@ -248,6 +251,9 b' class PrettyPrinter(_PrettyPrinterBase):'
         """
         Explicitly insert a newline into the output, maintaining correct indentation.
         """
+        group = self.group_queue.deq()
+        if group:
+            self._break_one_group(group)
         self.flush()
         self.output.write(self.newline)
         self.output.write(' ' * self.indentation)
@@ -688,9 +694,7 b' def _repr_pprint(obj, p, cycle):'
     # Find newlines and replace them with p.break_()
     output = repr(obj)
     lines = output.splitlines()
-    # insert a leading newline for multi-line objects that are indented
-    if len(lines) > 1 and p.indentation != p.output_width:
-        p.break_()
+    with p.group():
     for idx, output_line in enumerate(lines):
         if idx:
             p.break_()