diff --git a/news/5540.bugfix.rst b/news/5540.bugfix.rst
new file mode 100644
index 0000000000..da5c5b60a7
--- /dev/null
+++ b/news/5540.bugfix.rst
@@ -0,0 +1 @@
+Fix: `update --outdated` raises NonExistentKey with outdated dev packages
diff --git a/pipenv/core.py b/pipenv/core.py
index 771e8eea7b..677845853c 100644
--- a/pipenv/core.py
+++ b/pipenv/core.py
@@ -2081,7 +2081,9 @@ def do_outdated(project, pypi_mirror=None, pre=False, clear=False):
             )
             if name_in_pipfile:
                 required = ""
-                version = get_version(project.packages[name_in_pipfile])
+                version = get_version(
+                    project.get_pipfile_section(category)[name_in_pipfile]
+                )
                 rdeps = reverse_deps.get(canonicalize_name(package))
                 if isinstance(rdeps, Mapping) and "required" in rdeps:
                     required = " {} required".format(rdeps["required"])
diff --git a/pyproject.toml b/pyproject.toml
index 3b12f890ba..5c0eb6cdf3 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -78,6 +78,7 @@ filterwarnings = [
 # `pipenv run pytest --markers` will list all markers inlcuding these
 markers = [
     "install: tests having to do with `pipenv install`",
+    "update: tests having to do with `pipenv update`",
     "needs_internet: integration tests that require internet to pass",
     "basic: basic pipenv tests grouping",
     "dev: tests having to do with dev and dev packages",
diff --git a/tests/integration/test_update.py b/tests/integration/test_update.py
new file mode 100644
index 0000000000..e9db40b9fe
--- /dev/null
+++ b/tests/integration/test_update.py
@@ -0,0 +1,12 @@
+import pytest
+
+@pytest.mark.parametrize("cmd_option", ["", "--dev"])
+@pytest.mark.basic
+@pytest.mark.update
+def test_update_outdated_with_outdated_package(pipenv_instance_private_pypi, cmd_option):
+    with pipenv_instance_private_pypi() as p:
+        package_name = "six"
+        p.pipenv(f"install {cmd_option} {package_name}==1.11")
+        c = p.pipenv("update --outdated")
+        assert isinstance(c.exception, SystemExit)
+        assert c.stdout_bytes.decode("utf-8").startswith(f"Package '{package_name}' out-of-date:")