diff --git a/poetry.lock b/poetry.lock
index 05250649..afa6643c 100644
--- a/poetry.lock
+++ b/poetry.lock
@@ -1,4 +1,4 @@
-# This file is automatically @generated by Poetry 2.1.3 and should not be changed by hand.
+# This file is automatically @generated by Poetry 2.1.1 and should not be changed by hand.
 
 [[package]]
 name = "alabaster"
@@ -763,7 +763,7 @@ description = "Backport of PEP 654 (exception groups)"
 optional = false
 python-versions = ">=3.7"
 groups = ["main", "dev"]
-markers = "python_version == \"3.10\""
+markers = "python_version < \"3.11\""
 files = [
     {file = "exceptiongroup-1.2.2-py3-none-any.whl", hash = "sha256:3111b9d131c238bec2f8f516e123e14ba243563fb135d3fe885990585aa7795b"},
     {file = "exceptiongroup-1.2.2.tar.gz", hash = "sha256:47c2edf7c6738fafb49fd34290706d1a1a2f4d1c6df275526b62cbb4aa5393cc"},
@@ -2613,22 +2613,19 @@ files = [
 
 [[package]]
 name = "questionary"
-version = "1.10.0"
+version = "2.1.1"
 description = "Python library to build pretty command line user prompts ⭐️"
 optional = false
-python-versions = ">=3.6,<4.0"
+python-versions = ">=3.9"
 groups = ["main"]
 files = [
-    {file = "questionary-1.10.0-py3-none-any.whl", hash = "sha256:fecfcc8cca110fda9d561cb83f1e97ecbb93c613ff857f655818839dac74ce90"},
-    {file = "questionary-1.10.0.tar.gz", hash = "sha256:600d3aefecce26d48d97eee936fdb66e4bc27f934c3ab6dd1e292c4f43946d90"},
+    {file = "questionary-2.1.1-py3-none-any.whl", hash = "sha256:a51af13f345f1cdea62347589fbb6df3b290306ab8930713bfae4d475a7d4a59"},
+    {file = "questionary-2.1.1.tar.gz", hash = "sha256:3d7e980292bb0107abaa79c68dd3eee3c561b83a0f89ae482860b181c8bd412d"},
 ]
 
 [package.dependencies]
 prompt_toolkit = ">=2.0,<4.0"
 
-[package.extras]
-docs = ["Sphinx (>=3.3,<4.0)", "sphinx-autobuild (>=2020.9.1,<2021.0.0)", "sphinx-autodoc-typehints (>=1.11.1,<2.0.0)", "sphinx-copybutton (>=0.3.1,<0.4.0)", "sphinx-rtd-theme (>=0.5.0,<0.6.0)"]
-
 [[package]]
 name = "readme-renderer"
 version = "43.0"
@@ -3131,7 +3128,7 @@ files = [
     {file = "tomli-2.2.1-py3-none-any.whl", hash = "sha256:cb55c73c5f4408779d0cf3eef9f762b9c9f147a77de7b258bef0a5628adc85cc"},
     {file = "tomli-2.2.1.tar.gz", hash = "sha256:cd45e1dc79c835ce60f7404ec8119f2eb06d38b1deba146f07ced3bbc44505ff"},
 ]
-markers = {main = "python_version == \"3.10\"", dev = "python_full_version <= \"3.11.0a6\""}
+markers = {main = "python_version < \"3.11\"", dev = "python_full_version <= \"3.11.0a6\""}
 
 [[package]]
 name = "tomlkit"
@@ -3394,4 +3391,4 @@ type = ["pytest-mypy"]
 [metadata]
 lock-version = "2.1"
 python-versions = ">=3.10,<3.14"
-content-hash = "f625a9a82a2faa5d63c058dbffb03bb8b6a353d0774f20adbc4c572e59d28205"
+content-hash = "454c96f08f508219cadc7f456304b77ea3f97cef36f2f6e2ee25302ff0c71adf"
diff --git a/pyproject.toml b/pyproject.toml
index 98355f18..96e5c1bd 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -11,7 +11,7 @@ python = ">=3.10,<3.14"
 click = "8.1.8" # TODO: 8.2.0 upgrade requires refinements in click_invoker.py due to breaking changes
 httpx = ">=0.23.1,<=0.28.1"
 copier = "9.10.1" # Pinned as we have seen breaking changes in minor releases. Updates should be tested before bumping.
-questionary = "^1.10.0"
+questionary = ">=1.10,<3.0"
 pyclip = "^0.7.0"
 shellingham = "^1.5.4"
 tomli = { version = "^2.0.1", python = "<3.11" }