diff --git a/acceptance/bundle/exec/basic/test.toml b/acceptance/bundle/exec/basic/test.toml
new file mode 100644
index 000000000..ca7d069ae
--- /dev/null
+++ b/acceptance/bundle/exec/basic/test.toml
@@ -0,0 +1,3 @@
+[[Repls]]
+Old = "%PATH%"
+New = "$PATH"
diff --git a/acceptance/bundle/exec/cmd-not-found/test.toml b/acceptance/bundle/exec/cmd-not-found/test.toml
new file mode 100644
index 000000000..ca7d069ae
--- /dev/null
+++ b/acceptance/bundle/exec/cmd-not-found/test.toml
@@ -0,0 +1,3 @@
+[[Repls]]
+Old = "%PATH%"
+New = "$PATH"
diff --git a/acceptance/bundle/exec/cwd/a/b/c/.gitkeep b/acceptance/bundle/exec/cwd/unix/a/b/c/.gitkeep
similarity index 100%
rename from acceptance/bundle/exec/cwd/a/b/c/.gitkeep
rename to acceptance/bundle/exec/cwd/unix/a/b/c/.gitkeep
diff --git a/acceptance/bundle/exec/cwd/databricks.yml b/acceptance/bundle/exec/cwd/unix/databricks.yml
similarity index 100%
rename from acceptance/bundle/exec/cwd/databricks.yml
rename to acceptance/bundle/exec/cwd/unix/databricks.yml
diff --git a/acceptance/bundle/exec/cwd/output.txt b/acceptance/bundle/exec/cwd/unix/output.txt
similarity index 100%
rename from acceptance/bundle/exec/cwd/output.txt
rename to acceptance/bundle/exec/cwd/unix/output.txt
diff --git a/acceptance/bundle/exec/cwd/script b/acceptance/bundle/exec/cwd/unix/script
similarity index 100%
rename from acceptance/bundle/exec/cwd/script
rename to acceptance/bundle/exec/cwd/unix/script
diff --git a/acceptance/bundle/exec/cwd/unix/test.toml b/acceptance/bundle/exec/cwd/unix/test.toml
new file mode 100644
index 000000000..7f30bdcde
--- /dev/null
+++ b/acceptance/bundle/exec/cwd/unix/test.toml
@@ -0,0 +1,4 @@
+[GOOS]
+windows = false
+linux = true
+darwin = true
diff --git a/acceptance/bundle/exec/cwd/windows/a/b/c/.gitkeep b/acceptance/bundle/exec/cwd/windows/a/b/c/.gitkeep
new file mode 100644
index 000000000..e69de29bb
diff --git a/acceptance/bundle/exec/cwd/windows/databricks.yml b/acceptance/bundle/exec/cwd/windows/databricks.yml
new file mode 100644
index 000000000..432311dab
--- /dev/null
+++ b/acceptance/bundle/exec/cwd/windows/databricks.yml
@@ -0,0 +1,2 @@
+bundle:
+  name: foobar
diff --git a/acceptance/bundle/exec/cwd/windows/output.txt b/acceptance/bundle/exec/cwd/windows/output.txt
new file mode 100644
index 000000000..e6496afab
--- /dev/null
+++ b/acceptance/bundle/exec/cwd/windows/output.txt
@@ -0,0 +1,8 @@
+
+>>> cd a/b/c
+
+>>> pwd
+[TMPDIR]/a/b/c
+
+>>> [CLI] bundle exec -- pwd
+[TMPDIR]
diff --git a/acceptance/bundle/exec/cwd/windows/script b/acceptance/bundle/exec/cwd/windows/script
new file mode 100644
index 000000000..3461f6afc
--- /dev/null
+++ b/acceptance/bundle/exec/cwd/windows/script
@@ -0,0 +1,6 @@
+trace cd a/b/c
+
+trace pwd
+
+# Scripts that bundle exec executes should run from the bundle root.
+trace $CLI bundle exec -- dir
diff --git a/acceptance/bundle/exec/cwd/windows/test.toml b/acceptance/bundle/exec/cwd/windows/test.toml
new file mode 100644
index 000000000..22f2c79f0
--- /dev/null
+++ b/acceptance/bundle/exec/cwd/windows/test.toml
@@ -0,0 +1,4 @@
+[GOOS]
+windows = true
+linux = false
+darwin = false