diff --git a/.release-notes/4464.md b/.release-notes/4464.md
new file mode 100644
index 0000000000..84168da527
--- /dev/null
+++ b/.release-notes/4464.md
@@ -0,0 +1,40 @@
+## Disallow `return` at the end of a `with` block
+
+When we reimplemented `with` blocks in 2022, we allowed the usage of `return` at the end of the block. Recent analysis of the generated LLVM flagged incorrect LLVM IR that was generated from such code.
+
+Upon review, we realized that `return` at the end of a `with` block should be disallowed in the same way that `return` at the end of a method is disallowed.
+
+This a breaking change. If you had code such as:
+
+```pony
+actor Main
+  new create(env: Env) =>
+    with d = Disposble do
+      d.set_exit(10)
+      return
+    end
+```
+
+You'll need to update it to:
+
+```pony
+actor Main
+  new create(env: Env) =>
+    with d = Disposble do
+      d.set_exit(10)
+    end
+```
+
+The above examples are semantically the same. This also fixes a compiler crash if you had something along the lines of:
+
+```pony
+actor Main
+  new create(env: Env) =>
+    with d = Disposble do
+      d.set_exit(10)
+      return
+    end
+    let x = "foo"
+```
+
+Where you had code "after the return" which would be unexpected by the compiler.
diff --git a/src/libponyc/expr/control.c b/src/libponyc/expr/control.c
index 72f3f255b0..40dd2f442a 100644
--- a/src/libponyc/expr/control.c
+++ b/src/libponyc/expr/control.c
@@ -444,6 +444,13 @@ bool expr_return(pass_opt_t* opt, ast_t* ast)
     return false;
   }
 
+  if(ast_id(parent) == TK_DISPOSING_BLOCK)
+  {
+    ast_error(opt->check.errors, ast,
+      "use return only to exit early from a with block, not at the end");
+    return false;
+  }
+
   ast_t* type = ast_childidx(opt->check.frame->method, 4);
   ast_t* body = ast_child(ast);
 
diff --git a/test/full-program-tests/with-return/expected-exit-code.txt b/test/full-program-tests/with-return/expected-exit-code.txt
deleted file mode 100644
index f599e28b8a..0000000000
--- a/test/full-program-tests/with-return/expected-exit-code.txt
+++ /dev/null
@@ -1 +0,0 @@
-10
diff --git a/test/full-program-tests/with-return/main.pony b/test/full-program-tests/with-return/main.pony
deleted file mode 100644
index d234b723ed..0000000000
--- a/test/full-program-tests/with-return/main.pony
+++ /dev/null
@@ -1,20 +0,0 @@
-use @pony_exitcode[None](code: I32)
-
-class Disposble
-  var _exit_code: I32
-
-  new create() =>
-    _exit_code = 0
-
-  fun ref set_exit(code: I32) =>
-    _exit_code = code
-
-  fun dispose() =>
-    @pony_exitcode(_exit_code)
-
-actor Main
-  new create(env: Env) =>
-    with d = Disposble do
-      d.set_exit(10)
-      return
-    end
diff --git a/test/libponyc/CMakeLists.txt b/test/libponyc/CMakeLists.txt
index c3590aa2e7..2ccaa7ad90 100644
--- a/test/libponyc/CMakeLists.txt
+++ b/test/libponyc/CMakeLists.txt
@@ -52,6 +52,7 @@ add_executable(libponyc.tests
     use.cc
     util.cc
     verify.cc
+    with.cc
 )
 
 target_include_directories(libponyc.tests
diff --git a/test/libponyc/with.cc b/test/libponyc/with.cc
new file mode 100644
index 0000000000..a7980db89c
--- /dev/null
+++ b/test/libponyc/with.cc
@@ -0,0 +1,33 @@
+#include <gtest/gtest.h>
+#include <platform.h>
+
+#include "util.h"
+
+
+#define TEST_COMPILE(src) DO(test_compile(src, "expr"))
+
+#define TEST_ERRORS_1(src, err1) \
+  { const char* errs[] = {err1, NULL}; \
+    DO(test_expected_errors(src, "expr", errs)); }
+
+class WithTest : public PassTest
+{};
+
+TEST_F(WithTest, NoEarlyReturnFromWith)
+{
+  // From issue #4464
+  const char* src =
+    "class Disposable\n"
+    "  new create() => None\n"
+    "  fun ref set_exit(x: U32) => None\n"
+    "  fun dispose() => None\n"
+    "actor Main\n"
+    "  new create(env: Env) =>\n"
+    "    with d = Disposable do\n"
+    "      d.set_exit(10)\n"
+    "      return\n"
+    "    end";
+
+  TEST_ERRORS_1(src,
+    "use return only to exit early from a with block, not at the end");
+}