diff --git a/tests/functional/repl_characterization/data/regression_9917.nix b/tests/functional/repl_characterization/data/regression_9917.nix
new file mode 100644
index 000000000..ab49ce3a2
--- /dev/null
+++ b/tests/functional/repl_characterization/data/regression_9917.nix
@@ -0,0 +1,9 @@
+let
+  a = builtins.trace "before inner break" (
+    builtins.break { msg = "hello"; }
+  );
+  b = builtins.trace "before outer break" (
+    builtins.break a
+  );
+in
+  b
diff --git a/tests/functional/repl_characterization/data/regression_9917.test b/tests/functional/repl_characterization/data/regression_9917.test
new file mode 100644
index 000000000..a37ea5805
--- /dev/null
+++ b/tests/functional/repl_characterization/data/regression_9917.test
@@ -0,0 +1,14 @@
+https://github.com/NixOS/nix/pull/9917 (Enter debugger more reliably in let expressions and function calls)
+
+This test ensures that continues don't skip opportunities to enter the debugger.
+  trace: before outer break
+  info: breakpoint reached
+
+  nix-repl> :c
+  trace: before inner break
+  info: breakpoint reached
+
+  nix-repl> :c
+
+  nix-repl> msg
+  "hello"
diff --git a/tests/functional/repl_characterization/data/regression_9918.nix b/tests/functional/repl_characterization/data/regression_9918.nix
new file mode 100644
index 000000000..3860ce70e
--- /dev/null
+++ b/tests/functional/repl_characterization/data/regression_9918.nix
@@ -0,0 +1,5 @@
+let
+  r = [];
+  x = builtins.throw r;
+in
+  x
diff --git a/tests/functional/repl_characterization/data/regression_9918.test b/tests/functional/repl_characterization/data/regression_9918.test
new file mode 100644
index 000000000..4a1931122
--- /dev/null
+++ b/tests/functional/repl_characterization/data/regression_9918.test
@@ -0,0 +1,16 @@
+  error:
+         … while evaluating the error message passed to builtin.throw
+
+         error: cannot coerce a list to a string: [ ]
+
+We expect to be able to see locals like r in the debugger:
+
+  nix-repl> r
+  [ ]
+
+  nix-repl> :env
+  Env level 0
+  static: x r
+
+  Env level 1
+  builtins true false null scopedImport import isNull break abort throw derivationStrict placeholder baseNameOf dirOf removeAttrs map toString fetchMercurial fetchTree fetchTarball fetchGit fromTOML derivation
diff --git a/tests/functional/repl_characterization/repl_characterization.cc b/tests/functional/repl_characterization/repl_characterization.cc
index 395018299..a8d6c6d83 100644
--- a/tests/functional/repl_characterization/repl_characterization.cc
+++ b/tests/functional/repl_characterization/repl_characterization.cc
@@ -94,4 +94,15 @@ TEST_F(ReplSessionTest, repl_basic)
     readTest("basic_repl.test", [this](std::string input) { runReplTest(input); });
 }
 
+#define DEBUGGER_TEST(name) \
+    TEST_F(ReplSessionTest, name) \
+    { \
+        readTest(#name ".test", [this](std::string input) { \
+            runReplTest(input, {"--debugger", "-f", goldenMaster(#name ".nix")}); \
+        }); \
+    }
+
+DEBUGGER_TEST(regression_9918);
+DEBUGGER_TEST(regression_9917);
+
 };