diff --git a/Include/cpython/optimizer.h b/Include/cpython/optimizer.h
index 10457afc180a00..2f891a676d2b54 100644
--- a/Include/cpython/optimizer.h
+++ b/Include/cpython/optimizer.h
@@ -14,7 +14,7 @@ typedef struct {
 typedef struct _PyExecutorObject {
     PyObject_VAR_HEAD
     /* WARNING: execute consumes a reference to self. This is necessary to allow executors to tail call into each other. */
-    struct _PyInterpreterFrame *(*execute)(struct _PyExecutorObject *self, struct _PyInterpreterFrame *frame, PyObject **stack_pointer);
+    _Py_CODEUNIT *(*execute)(struct _PyExecutorObject *self, struct _PyInterpreterFrame *frame, PyObject **stack_pointer);
     _PyVMData vm_data; /* Used by the VM, but opaque to the optimizer */
     /* Data needed by the executor goes here, but is opaque to the VM */
 } _PyExecutorObject;
@@ -40,7 +40,7 @@ PyAPI_FUNC(_PyOptimizerObject *) PyUnstable_GetOptimizer(void);
 
 PyAPI_FUNC(_PyExecutorObject *) PyUnstable_GetExecutor(PyCodeObject *code, int offset);
 
-struct _PyInterpreterFrame *
+_Py_CODEUNIT *
 _PyOptimizer_BackEdge(struct _PyInterpreterFrame *frame, _Py_CODEUNIT *src, _Py_CODEUNIT *dest, PyObject **stack_pointer);
 
 extern _PyOptimizerObject _PyOptimizer_Default;
diff --git a/Include/internal/pycore_opcode_metadata.h b/Include/internal/pycore_opcode_metadata.h
index fb5c0465a10021..d0d452f1ef5dc5 100644
--- a/Include/internal/pycore_opcode_metadata.h
+++ b/Include/internal/pycore_opcode_metadata.h
@@ -1372,7 +1372,7 @@ const struct opcode_metadata _PyOpcode_opcode_metadata[OPCODE_METADATA_SIZE] = {
     [JUMP_BACKWARD] = { true, INSTR_FMT_IB, HAS_ARG_FLAG | HAS_JUMP_FLAG | HAS_EVAL_BREAK_FLAG | HAS_ERROR_FLAG },
     [JUMP] = { true, INSTR_FMT_IB, HAS_ARG_FLAG | HAS_JUMP_FLAG },
     [JUMP_NO_INTERRUPT] = { true, INSTR_FMT_IB, HAS_ARG_FLAG | HAS_JUMP_FLAG },
-    [ENTER_EXECUTOR] = { true, INSTR_FMT_IB, HAS_ARG_FLAG | HAS_JUMP_FLAG | HAS_EVAL_BREAK_FLAG | HAS_ERROR_FLAG },
+    [ENTER_EXECUTOR] = { true, INSTR_FMT_IB, HAS_ARG_FLAG | HAS_EVAL_BREAK_FLAG | HAS_ERROR_FLAG },
     [POP_JUMP_IF_FALSE] = { true, INSTR_FMT_IB, HAS_ARG_FLAG | HAS_JUMP_FLAG },
     [POP_JUMP_IF_TRUE] = { true, INSTR_FMT_IB, HAS_ARG_FLAG | HAS_JUMP_FLAG },
     [IS_NONE] = { true, INSTR_FMT_IX, 0 },
diff --git a/Include/internal/pycore_uops.h b/Include/internal/pycore_uops.h
index 249f5c010e0092..4e664632ec73dc 100644
--- a/Include/internal/pycore_uops.h
+++ b/Include/internal/pycore_uops.h
@@ -23,7 +23,7 @@ typedef struct {
     _PyUOpInstruction trace[1];
 } _PyUOpExecutorObject;
 
-_PyInterpreterFrame *_PyUopExecute(
+_Py_CODEUNIT *_PyUopExecute(
     _PyExecutorObject *executor,
     _PyInterpreterFrame *frame,
     PyObject **stack_pointer);
diff --git a/Misc/NEWS.d/next/Core and Builtins/2023-09-07-04-50-19.gh-issue-108866.xbJ-9a.rst b/Misc/NEWS.d/next/Core and Builtins/2023-09-07-04-50-19.gh-issue-108866.xbJ-9a.rst
new file mode 100644
index 00000000000000..96606924d4a3ec
--- /dev/null
+++ b/Misc/NEWS.d/next/Core and Builtins/2023-09-07-04-50-19.gh-issue-108866.xbJ-9a.rst	
@@ -0,0 +1,3 @@
+Change the API and contract of ``_PyExecutorObject`` to return the
+next_instr pointer, instead of the frame, and to always execute at least one
+instruction.
diff --git a/Python/bytecodes.c b/Python/bytecodes.c
index 8820b52774671b..354cffca27333f 100644
--- a/Python/bytecodes.c
+++ b/Python/bytecodes.c
@@ -2218,23 +2218,25 @@ dummy_func(
             JUMPBY(1-oparg);
             #if ENABLE_SPECIALIZATION
             here[1].cache += (1 << OPTIMIZER_BITS_IN_COUNTER);
-            if (here[1].cache > tstate->interp->optimizer_backedge_threshold &&
-                // Double-check that the opcode isn't instrumented or something:
-                here->op.code == JUMP_BACKWARD &&
-                // _PyOptimizer_BackEdge is going to change frame->prev_instr,
-                // which breaks line event calculations:
-                next_instr->op.code != INSTRUMENTED_LINE
-                )
-            {
+            if (here[1].cache > tstate->interp->optimizer_backedge_threshold) {
+                /* We should not be here if the code has been instrumented,
+                 * or already has an attached executor */
+                assert(here->op.code != ENTER_EXECUTOR);
+                assert(here->op.code != INSTRUMENTED_JUMP_BACKWARD);
                 OBJECT_STAT_INC(optimization_attempts);
-                frame = _PyOptimizer_BackEdge(frame, here, next_instr, stack_pointer);
-                if (frame == NULL) {
-                    frame = tstate->current_frame;
+                _Py_CODEUNIT *src = here;
+                while(oparg > 255) {
+                    oparg >>= 8;
+                    src--;
+                    assert(src->op.code == EXTENDED_ARG);
+                }
+                next_instr = _PyOptimizer_BackEdge(frame, src, next_instr, stack_pointer);
+                frame = tstate->current_frame;
+                if (next_instr == NULL) {
                     goto resume_with_error;
                 }
-                assert(frame == tstate->current_frame);
+                stack_pointer = _PyFrame_GetStackPointer(frame);
                 here[1].cache &= ((1 << OPTIMIZER_BITS_IN_COUNTER) -1);
-                goto resume_frame;
             }
             #endif  /* ENABLE_SPECIALIZATION */
         }
@@ -2251,19 +2253,15 @@ dummy_func(
 
         inst(ENTER_EXECUTOR, (--)) {
             CHECK_EVAL_BREAKER();
-
             PyCodeObject *code = _PyFrame_GetCode(frame);
             _PyExecutorObject *executor = (_PyExecutorObject *)code->co_executors->executors[oparg&255];
-            int original_oparg = executor->vm_data.oparg | (oparg & 0xfffff00);
-            JUMPBY(1-original_oparg);
-            frame->prev_instr = next_instr - 1;
             Py_INCREF(executor);
-            frame = executor->execute(executor, frame, stack_pointer);
-            if (frame == NULL) {
-                frame = tstate->current_frame;
+            next_instr = executor->execute(executor, frame, stack_pointer);
+            frame = tstate->current_frame;
+            if (next_instr == NULL) {
                 goto resume_with_error;
             }
-            goto resume_frame;
+            stack_pointer = _PyFrame_GetStackPointer(frame);
         }
 
         inst(POP_JUMP_IF_FALSE, (cond -- )) {
@@ -3821,10 +3819,9 @@ dummy_func(
         }
 
         op(EXIT_TRACE, (--)) {
-            frame->prev_instr--;  // Back up to just before destination
             _PyFrame_SetStackPointer(frame, stack_pointer);
             Py_DECREF(self);
-            return frame;
+            return frame->prev_instr;
         }
 
         op(INSERT, (unused[oparg], top -- top, unused[oparg])) {
diff --git a/Python/executor.c b/Python/executor.c
index ac9104223da8ff..c37f5ffab4ea09 100644
--- a/Python/executor.c
+++ b/Python/executor.c
@@ -34,7 +34,7 @@
 #define ENABLE_SPECIALIZATION 0
 
 
-_PyInterpreterFrame *
+_Py_CODEUNIT *
 _PyUopExecute(_PyExecutorObject *executor, _PyInterpreterFrame *frame, PyObject **stack_pointer)
 {
 #ifdef Py_DEBUG
@@ -122,8 +122,7 @@ _PyUopExecute(_PyExecutorObject *executor, _PyInterpreterFrame *frame, PyObject
     // On DEOPT_IF we just repeat the last instruction.
     // This presumes nothing was popped from the stack (nor pushed).
     DPRINTF(2, "DEOPT: [Opcode %d, operand %" PRIu64 "]\n", opcode, operand);
-    frame->prev_instr--;  // Back up to just before destination
     _PyFrame_SetStackPointer(frame, stack_pointer);
     Py_DECREF(self);
-    return frame;
+    return frame->prev_instr;
 }
diff --git a/Python/executor_cases.c.h b/Python/executor_cases.c.h
index f4c526a5a8c0a2..0edb6c0d17af5c 100644
--- a/Python/executor_cases.c.h
+++ b/Python/executor_cases.c.h
@@ -2874,10 +2874,9 @@
         }
 
         case EXIT_TRACE: {
-            frame->prev_instr--;  // Back up to just before destination
             _PyFrame_SetStackPointer(frame, stack_pointer);
             Py_DECREF(self);
-            return frame;
+            return frame->prev_instr;
             break;
         }
 
diff --git a/Python/generated_cases.c.h b/Python/generated_cases.c.h
index 84f83db128ea50..8e02485532d29b 100644
--- a/Python/generated_cases.c.h
+++ b/Python/generated_cases.c.h
@@ -2966,23 +2966,25 @@
             JUMPBY(1-oparg);
             #if ENABLE_SPECIALIZATION
             here[1].cache += (1 << OPTIMIZER_BITS_IN_COUNTER);
-            if (here[1].cache > tstate->interp->optimizer_backedge_threshold &&
-                // Double-check that the opcode isn't instrumented or something:
-                here->op.code == JUMP_BACKWARD &&
-                // _PyOptimizer_BackEdge is going to change frame->prev_instr,
-                // which breaks line event calculations:
-                next_instr->op.code != INSTRUMENTED_LINE
-                )
-            {
+            if (here[1].cache > tstate->interp->optimizer_backedge_threshold) {
+                /* We should not be here if the code has been instrumented,
+                 * or already has an attached executor */
+                assert(here->op.code != ENTER_EXECUTOR);
+                assert(here->op.code != INSTRUMENTED_JUMP_BACKWARD);
                 OBJECT_STAT_INC(optimization_attempts);
-                frame = _PyOptimizer_BackEdge(frame, here, next_instr, stack_pointer);
-                if (frame == NULL) {
-                    frame = tstate->current_frame;
+                _Py_CODEUNIT *src = here;
+                while(oparg > 255) {
+                    oparg >>= 8;
+                    src--;
+                    assert(src->op.code == EXTENDED_ARG);
+                }
+                next_instr = _PyOptimizer_BackEdge(frame, src, next_instr, stack_pointer);
+                frame = tstate->current_frame;
+                if (next_instr == NULL) {
                     goto resume_with_error;
                 }
-                assert(frame == tstate->current_frame);
+                stack_pointer = _PyFrame_GetStackPointer(frame);
                 here[1].cache &= ((1 << OPTIMIZER_BITS_IN_COUNTER) -1);
-                goto resume_frame;
             }
             #endif  /* ENABLE_SPECIALIZATION */
             DISPATCH();
@@ -2990,19 +2992,16 @@
 
         TARGET(ENTER_EXECUTOR) {
             CHECK_EVAL_BREAKER();
-
             PyCodeObject *code = _PyFrame_GetCode(frame);
             _PyExecutorObject *executor = (_PyExecutorObject *)code->co_executors->executors[oparg&255];
-            int original_oparg = executor->vm_data.oparg | (oparg & 0xfffff00);
-            JUMPBY(1-original_oparg);
-            frame->prev_instr = next_instr - 1;
             Py_INCREF(executor);
-            frame = executor->execute(executor, frame, stack_pointer);
-            if (frame == NULL) {
-                frame = tstate->current_frame;
+            next_instr = executor->execute(executor, frame, stack_pointer);
+            frame = tstate->current_frame;
+            if (next_instr == NULL) {
                 goto resume_with_error;
             }
-            goto resume_frame;
+            stack_pointer = _PyFrame_GetStackPointer(frame);
+            DISPATCH();
         }
 
         TARGET(POP_JUMP_IF_FALSE) {
diff --git a/Python/optimizer.c b/Python/optimizer.c
index c6d0f9e5bf22d7..9e57316115303a 100644
--- a/Python/optimizer.c
+++ b/Python/optimizer.c
@@ -153,10 +153,10 @@ PyUnstable_SetOptimizer(_PyOptimizerObject *optimizer)
     Py_DECREF(old);
 }
 
-_PyInterpreterFrame *
+_Py_CODEUNIT *
 _PyOptimizer_BackEdge(_PyInterpreterFrame *frame, _Py_CODEUNIT *src, _Py_CODEUNIT *dest, PyObject **stack_pointer)
 {
-    assert(src->op.code == JUMP_BACKWARD);
+    assert(src->op.code == EXTENDED_ARG || src->op.code == JUMP_BACKWARD);
     PyCodeObject *code = (PyCodeObject *)frame->f_executable;
     assert(PyCode_Check(code));
     PyInterpreterState *interp = _PyInterpreterState_GET();
@@ -165,7 +165,7 @@ _PyOptimizer_BackEdge(_PyInterpreterFrame *frame, _Py_CODEUNIT *src, _Py_CODEUNI
     }
     _PyOptimizerObject *opt = interp->optimizer;
     _PyExecutorObject *executor = NULL;
-    int err = opt->optimize(opt, code, dest, &executor, (int)(stack_pointer - _PyFrame_Stackbase(frame)));
+    int err = opt->optimize(opt, code, src, &executor, (int)(stack_pointer - _PyFrame_Stackbase(frame)));
     if (err <= 0) {
         assert(executor == NULL);
         if (err < 0) {
@@ -186,13 +186,11 @@ _PyOptimizer_BackEdge(_PyInterpreterFrame *frame, _Py_CODEUNIT *src, _Py_CODEUNI
         goto jump_to_destination;
     }
     insert_executor(code, src, index, executor);
-    assert(frame->prev_instr == src);
-    frame->prev_instr = dest - 1;
     return executor->execute(executor, frame, stack_pointer);
 jump_to_destination:
     frame->prev_instr = dest - 1;
     _PyFrame_SetStackPointer(frame, stack_pointer);
-    return frame;
+    return dest;
 }
 
 _PyExecutorObject *
@@ -241,14 +239,13 @@ static PyTypeObject CounterExecutor_Type = {
     .tp_dealloc = (destructor)counter_dealloc,
 };
 
-static _PyInterpreterFrame *
+static _Py_CODEUNIT *
 counter_execute(_PyExecutorObject *self, _PyInterpreterFrame *frame, PyObject **stack_pointer)
 {
     ((_PyCounterExecutorObject *)self)->optimizer->count++;
     _PyFrame_SetStackPointer(frame, stack_pointer);
-    frame->prev_instr = ((_PyCounterExecutorObject *)self)->next_instr - 1;
     Py_DECREF(self);
-    return frame;
+    return ((_PyCounterExecutorObject *)self)->next_instr;
 }
 
 static int
@@ -266,8 +263,14 @@ counter_optimize(
     }
     executor->executor.execute = counter_execute;
     Py_INCREF(self);
+    int oparg = instr->op.arg;
+    while (instr->op.code == EXTENDED_ARG) {
+        instr++;
+        oparg = (oparg << 8) | instr->op.arg;
+    }
+    assert(instr->op.code == JUMP_BACKWARD);
     executor->optimizer = (_PyCounterOptimizerObject *)self;
-    executor->next_instr = instr;
+    executor->next_instr = instr + 2 - oparg;
     *exec_ptr = (_PyExecutorObject *)executor;
     return 1;
 }
@@ -880,6 +883,14 @@ uop_optimize(
     _PyExecutorObject **exec_ptr,
     int curr_stackentries)
 {
+    /* Do backwards jump before handing to trace generation */
+    int oparg = instr->op.arg;
+    while (instr->op.code == EXTENDED_ARG) {
+        instr++;
+        oparg = (oparg << 8) | instr->op.arg;
+    }
+    assert(instr->op.code == JUMP_BACKWARD);
+    instr += 2 - oparg;
     _PyUOpInstruction trace[_Py_UOP_MAX_TRACE_LENGTH];
     int trace_length = translate_bytecode_to_trace(code, instr, trace, _Py_UOP_MAX_TRACE_LENGTH);
     if (trace_length <= 0) {