diff --git a/Lib/test/test_sys_settrace.py b/Lib/test/test_sys_settrace.py
index 1f77f9b..57a7839 100644
--- a/Lib/test/test_sys_settrace.py
+++ b/Lib/test/test_sys_settrace.py
@@ -670,6 +670,14 @@
 no_jump_to_non_integers.jump = (2, "Spam")
 no_jump_to_non_integers.output = [True]
 
+def jump_across_with(output):
+    with open(test_support.TESTFN, "wb") as fp:
+        pass
+    with open(test_support.TESTFN, "wb") as fp:
+        pass
+jump_across_with.jump = (1, 3)
+jump_across_with.output = []
+
 # This verifies that you can't set f_lineno via _getframe or similar
 # trickery.
 def no_jump_without_trace_function():
@@ -739,6 +747,9 @@
         self.run_test(no_jump_to_non_integers)
     def test_19_no_jump_without_trace_function(self):
         no_jump_without_trace_function()
+    def test_jump_across_with(self):
+        self.addCleanup(test_support.unlink, test_support.TESTFN)
+        self.run_test(jump_across_with)
 
     def test_20_large_function(self):
         d = {}
diff --git a/Misc/NEWS b/Misc/NEWS
index 71218d7..6b278bd 100644
--- a/Misc/NEWS
+++ b/Misc/NEWS
@@ -9,6 +9,8 @@
 Core and Builtins
 -----------------
 
+- Issue #14612: Fix jumping around with blocks by setting f_lineno.
+
 - Issue #13889: Check and (if necessary) set FPU control word before calling
   any of the dtoa.c string <-> float conversion functions, on MSVC builds of
   Python.  This fixes issues when embedding Python in a Delphi app.
diff --git a/Objects/frameobject.c b/Objects/frameobject.c
index a3476cf..f9e4a0e 100644
--- a/Objects/frameobject.c
+++ b/Objects/frameobject.c
@@ -214,6 +214,7 @@
         case SETUP_LOOP:
         case SETUP_EXCEPT:
         case SETUP_FINALLY:
+        case SETUP_WITH:
             blockstack[blockstack_top++] = addr;
             in_finally[blockstack_top-1] = 0;
             break;
@@ -221,7 +222,7 @@
         case POP_BLOCK:
             assert(blockstack_top > 0);
             setup_op = code[blockstack[blockstack_top-1]];
-            if (setup_op == SETUP_FINALLY) {
+            if (setup_op == SETUP_FINALLY || setup_op == SETUP_WITH) {
                 in_finally[blockstack_top-1] = 1;
             }
             else {
@@ -236,7 +237,7 @@
              * be seeing such an END_FINALLY.) */
             if (blockstack_top > 0) {
                 setup_op = code[blockstack[blockstack_top-1]];
-                if (setup_op == SETUP_FINALLY) {
+                if (setup_op == SETUP_FINALLY || setup_op == SETUP_WITH) {
                     blockstack_top--;
                 }
             }
@@ -298,6 +299,7 @@
         case SETUP_LOOP:
         case SETUP_EXCEPT:
         case SETUP_FINALLY:
+        case SETUP_WITH:
             delta_iblock++;
             break;