diff --git a/Lib/test/test_trace.py b/Lib/test/test_trace.py
index 144fc66dcea..7f7db334ed0 100644
--- a/Lib/test/test_trace.py
+++ b/Lib/test/test_trace.py
@@ -252,14 +252,16 @@ class TraceTestCase(unittest.TestCase):
                 "\n".join(difflib.ndiff([str(x) for x in expected_events],
                                         [str(x) for x in events])))
 
-
-    def run_test(self, func):
+    def run_and_compare(self, func, events):
         tracer = Tracer()
         sys.settrace(tracer.trace)
         func()
         sys.settrace(None)
         self.compare_events(func.func_code.co_firstlineno,
-                            tracer.events, func.events)
+                            tracer.events, events)
+
+    def run_test(self, func):
+        self.run_and_compare(func, func.events)
 
     def run_test2(self, func):
         tracer = Tracer()
@@ -321,6 +323,49 @@ class TraceTestCase(unittest.TestCase):
         self.compare_events(generator_example.__code__.co_firstlineno,
                             tracer.events, generator_example.events)
 
+    def test_14_onliner_if(self):
+        def onliners():
+            if True: False
+            else: True
+            return 0
+        self.run_and_compare(
+            onliners,
+            [(0, 'call'),
+             (1, 'line'),
+             (3, 'line'),
+             (3, 'return')])
+
+    def test_15_loops(self):
+        # issue1750076: "while" expression is skipped by debugger
+        def for_example():
+            for x in range(2):
+                pass
+        self.run_and_compare(
+            for_example,
+            [(0, 'call'),
+             (1, 'line'),
+             (2, 'line'),
+             (1, 'line'),
+             (2, 'line'),
+             (1, 'line'),
+             (1, 'return')])
+
+        def while_example():
+            # While expression should be traced on every loop
+            x = 2
+            while x > 0:
+                x -= 1
+        self.run_and_compare(
+            while_example,
+            [(0, 'call'),
+             (2, 'line'),
+             (3, 'line'),
+             (4, 'line'),
+             (3, 'line'),
+             (4, 'line'),
+             (3, 'line'),
+             (3, 'return')])
+
 class RaisingTraceFuncTestCase(unittest.TestCase):
     def trace(self, frame, event, arg):
         """A trace function that raises an exception in response to a
diff --git a/Misc/NEWS b/Misc/NEWS
index 38dc8edcb20..8a4b4492a27 100644
--- a/Misc/NEWS
+++ b/Misc/NEWS
@@ -388,6 +388,10 @@ Core and builtins
 Library
 -------
 
+- #175006: The debugger used to skip the condition of a "while" statement
+  after the first iteration. Now it correctly steps on the expression, and
+  breakpoints on the "while" statement are honored on each loop.
+
 - #1765140: add an optional delay argument to FileHandler and its
   subclasses. Defaults to false (existing behaviour), but if true,
   defers opening the file until the first call to emit().
diff --git a/Python/compile.c b/Python/compile.c
index 0dd1082151e..f9b5ac4a523 100644
--- a/Python/compile.c
+++ b/Python/compile.c
@@ -638,11 +638,16 @@ compiler_next_instr(struct compiler *c, basicblock *b)
 	return b->b_iused++;
 }
 
-/* Set the i_lineno member of the instruction at offse off if the
-   line number for the current expression/statement (?) has not
+/* Set the i_lineno member of the instruction at offset off if the
+   line number for the current expression/statement has not
    already been set.  If it has been set, the call has no effect.
 
-   Every time a new node is b
+   The line number is reset in the following cases:
+   - when entering a new scope
+   - on each statement
+   - on each expression that start a new line
+   - before the "except" clause
+   - before the "for" and "while" expressions
 */
 
 static void
@@ -1611,9 +1616,8 @@ compiler_for(struct compiler *c, stmt_ty s)
 	VISIT(c, expr, s->v.For.iter);
 	ADDOP(c, GET_ITER);
 	compiler_use_next_block(c, start);
-	/* XXX(nnorwitz): is there a better way to handle this?
-	   for loops are special, we want to be able to trace them
-	   each time around, so we need to set an extra line number. */
+	/* for expressions must be traced on each iteration,
+	   so we need to set an extra line number. */
 	c->u->u_lineno_set = false;
 	ADDOP_JREL(c, FOR_ITER, cleanup);
 	VISIT(c, expr, s->v.For.target);
@@ -1660,6 +1664,9 @@ compiler_while(struct compiler *c, stmt_ty s)
 	if (!compiler_push_fblock(c, LOOP, loop))
 		return 0;
 	if (constant == -1) {
+		/* while expressions must be traced on each iteration,
+		   so we need to set an extra line number. */
+		c->u->u_lineno_set = false;
 		VISIT(c, expr, s->v.While.test);
 		ADDOP_JREL(c, JUMP_IF_FALSE, anchor);
 		ADDOP(c, POP_TOP);
@@ -1840,8 +1847,8 @@ compiler_try_except(struct compiler *c, stmt_ty s)
 						s->v.TryExcept.handlers, i);
 		if (!handler->type && i < n-1)
 		    return compiler_error(c, "default 'except:' must be last");
-	c->u->u_lineno_set = false;
-	c->u->u_lineno = handler->lineno;
+		c->u->u_lineno_set = false;
+		c->u->u_lineno = handler->lineno;
 		except = compiler_new_block(c);
 		if (except == NULL)
 			return 0;
@@ -3553,12 +3560,6 @@ assemble_lnotab(struct assembler *a, struct instr *i)
 	assert(d_bytecode >= 0);
 	assert(d_lineno >= 0);
 
-	/* XXX(nnorwitz): is there a better way to handle this?
-	   for loops are special, we want to be able to trace them
-	   each time around, so we need to set an extra line number. */
-	if (d_lineno == 0 && i->i_opcode != FOR_ITER)
-		return 1;
-
 	if (d_bytecode > 255) {
 		int j, nbytes, ncodes = d_bytecode / 255;
 		nbytes = a->a_lnotab_off + 2 * ncodes;