diff --git a/circleci/images/citusupgradetester/files/etc/requirements.txt b/circleci/images/citusupgradetester/files/etc/requirements.txt
index 0c9b89b..c5da543 100644
--- a/circleci/images/citusupgradetester/files/etc/requirements.txt
+++ b/circleci/images/citusupgradetester/files/etc/requirements.txt
@@ -1,4 +1,4 @@
-# generated from Citus's Pipfile.lock (in src/test/regress) as of citusdata/citus#8547
+# generated from Citus's Pipfile.lock (in src/test/regress) as of citusdata/citus#8596
 # using `pipenv requirements > requirements.txt`, so as to avoid the
 # need for pipenv/pyenv in this image
 
@@ -6,19 +6,19 @@
 aioquic==1.2.0; python_version >= '3.8'
 argon2-cffi==25.1.0; python_version >= '3.8'
 argon2-cffi-bindings==25.1.0; python_version >= '3.9'
-asgiref==3.11.0; python_version >= '3.9'
+asgiref==3.11.1; python_version >= '3.9'
 attrs==26.1.0; python_version >= '3.9'
 bcrypt==5.0.0; python_version >= '3.8'
 blinker==1.9.0; python_version >= '3.9'
 brotli==1.2.0
-certifi==2026.2.25; python_version >= '3.7'
+certifi==2026.5.20; python_version >= '3.7'
 cffi==2.0.0; python_version >= '3.9'
-click==8.3.2; python_version >= '3.10'
+click==8.4.1; python_version >= '3.10'
 construct==2.10.70; python_version >= '3.6'
 cryptography==46.0.7; python_version >= '3.8' and python_full_version not in '3.9.0, 3.9.1'
 docopt==0.6.2
 execnet==2.1.2; python_version >= '3.8'
-filelock==3.28.0; python_version >= '3.10'
+filelock==3.29.0; python_version >= '3.10'
 flask==3.1.3; python_version >= '3.9'
 h11==0.16.0; python_version >= '3.8'
 h2==4.3.0; python_version >= '3.9'
@@ -30,24 +30,24 @@ jinja2==3.1.6; python_version >= '3.7'
 kaitaistruct==0.11; python_version >= '2.7' and python_version not in '3.0, 3.1, 3.2, 3.3'
 ldap3==2.9.1
 markupsafe==3.0.3; python_version >= '3.9'
-mitmproxy @ git+https://github.com/citusdata/mitmproxy.git@70bad9a3c098f605e5f8b25553e5db5334018ff1
+mitmproxy @ git+https://github.com/citusdata/mitmproxy.git@df5879516a57ea780e1cc88edaf2051e1d32915f
 mitmproxy-linux==0.12.9; python_version >= '3.12'
 mitmproxy-rs==0.12.9; python_version >= '3.12'
 msgpack==1.1.2; python_version >= '3.9'
-packaging==26.1; python_version >= '3.8'
+packaging==26.2; python_version >= '3.8'
 pluggy==1.6.0; python_version >= '3.9'
-psycopg==3.3.3; python_version >= '3.10'
+psycopg==3.3.4; python_version >= '3.10'
 publicsuffix2==2.20191221
 pyasn1==0.6.3; python_version >= '3.8'
 pyasn1-modules==0.4.2; python_version >= '3.8'
 pycparser==3.0; python_version >= '3.10'
 pygments==2.20.0; python_version >= '3.9'
 pylsqpack==0.3.24; python_version >= '3.10'
-pyopenssl==25.3.0; python_version >= '3.7'
+pyopenssl==26.2.0; python_version >= '3.8'
 pyparsing==3.3.2; python_version >= '3.9'
 pyperclip==1.9.0
 pytest==9.0.3; python_version >= '3.10'
-pytest-asyncio==1.3.0; python_version >= '3.10'
+pytest-asyncio==1.4.0; python_version >= '3.10'
 pytest-repeat==0.9.4; python_version >= '3.9'
 pytest-timeout==2.4.0; python_version >= '3.7'
 pytest-xdist==3.8.0; python_version >= '3.9'
@@ -57,8 +57,8 @@ service-identity==24.2.0; python_version >= '3.8'
 sortedcontainers==2.4.0
 tornado==6.5.5; python_version >= '3.9'
 typing-extensions==4.14.0; python_version >= '3.9'
-urwid==3.0.5; python_full_version >= '3.9.0'
-wcwidth==0.6.0; python_version >= '3.8'
+urwid==4.0.0; python_full_version >= '3.9.0'
+wcwidth==0.7.0; python_version >= '3.8'
 werkzeug==3.1.6; python_version >= '3.9'
 wsproto==1.3.2; python_version >= '3.10'
 zstandard==0.25.0; python_version >= '3.9'
diff --git a/circleci/images/failtester/files/etc/requirements.txt b/circleci/images/failtester/files/etc/requirements.txt
index 0c9b89b..c5da543 100644
--- a/circleci/images/failtester/files/etc/requirements.txt
+++ b/circleci/images/failtester/files/etc/requirements.txt
@@ -1,4 +1,4 @@
-# generated from Citus's Pipfile.lock (in src/test/regress) as of citusdata/citus#8547
+# generated from Citus's Pipfile.lock (in src/test/regress) as of citusdata/citus#8596
 # using `pipenv requirements > requirements.txt`, so as to avoid the
 # need for pipenv/pyenv in this image
 
@@ -6,19 +6,19 @@
 aioquic==1.2.0; python_version >= '3.8'
 argon2-cffi==25.1.0; python_version >= '3.8'
 argon2-cffi-bindings==25.1.0; python_version >= '3.9'
-asgiref==3.11.0; python_version >= '3.9'
+asgiref==3.11.1; python_version >= '3.9'
 attrs==26.1.0; python_version >= '3.9'
 bcrypt==5.0.0; python_version >= '3.8'
 blinker==1.9.0; python_version >= '3.9'
 brotli==1.2.0
-certifi==2026.2.25; python_version >= '3.7'
+certifi==2026.5.20; python_version >= '3.7'
 cffi==2.0.0; python_version >= '3.9'
-click==8.3.2; python_version >= '3.10'
+click==8.4.1; python_version >= '3.10'
 construct==2.10.70; python_version >= '3.6'
 cryptography==46.0.7; python_version >= '3.8' and python_full_version not in '3.9.0, 3.9.1'
 docopt==0.6.2
 execnet==2.1.2; python_version >= '3.8'
-filelock==3.28.0; python_version >= '3.10'
+filelock==3.29.0; python_version >= '3.10'
 flask==3.1.3; python_version >= '3.9'
 h11==0.16.0; python_version >= '3.8'
 h2==4.3.0; python_version >= '3.9'
@@ -30,24 +30,24 @@ jinja2==3.1.6; python_version >= '3.7'
 kaitaistruct==0.11; python_version >= '2.7' and python_version not in '3.0, 3.1, 3.2, 3.3'
 ldap3==2.9.1
 markupsafe==3.0.3; python_version >= '3.9'
-mitmproxy @ git+https://github.com/citusdata/mitmproxy.git@70bad9a3c098f605e5f8b25553e5db5334018ff1
+mitmproxy @ git+https://github.com/citusdata/mitmproxy.git@df5879516a57ea780e1cc88edaf2051e1d32915f
 mitmproxy-linux==0.12.9; python_version >= '3.12'
 mitmproxy-rs==0.12.9; python_version >= '3.12'
 msgpack==1.1.2; python_version >= '3.9'
-packaging==26.1; python_version >= '3.8'
+packaging==26.2; python_version >= '3.8'
 pluggy==1.6.0; python_version >= '3.9'
-psycopg==3.3.3; python_version >= '3.10'
+psycopg==3.3.4; python_version >= '3.10'
 publicsuffix2==2.20191221
 pyasn1==0.6.3; python_version >= '3.8'
 pyasn1-modules==0.4.2; python_version >= '3.8'
 pycparser==3.0; python_version >= '3.10'
 pygments==2.20.0; python_version >= '3.9'
 pylsqpack==0.3.24; python_version >= '3.10'
-pyopenssl==25.3.0; python_version >= '3.7'
+pyopenssl==26.2.0; python_version >= '3.8'
 pyparsing==3.3.2; python_version >= '3.9'
 pyperclip==1.9.0
 pytest==9.0.3; python_version >= '3.10'
-pytest-asyncio==1.3.0; python_version >= '3.10'
+pytest-asyncio==1.4.0; python_version >= '3.10'
 pytest-repeat==0.9.4; python_version >= '3.9'
 pytest-timeout==2.4.0; python_version >= '3.7'
 pytest-xdist==3.8.0; python_version >= '3.9'
@@ -57,8 +57,8 @@ service-identity==24.2.0; python_version >= '3.8'
 sortedcontainers==2.4.0
 tornado==6.5.5; python_version >= '3.9'
 typing-extensions==4.14.0; python_version >= '3.9'
-urwid==3.0.5; python_full_version >= '3.9.0'
-wcwidth==0.6.0; python_version >= '3.8'
+urwid==4.0.0; python_full_version >= '3.9.0'
+wcwidth==0.7.0; python_version >= '3.8'
 werkzeug==3.1.6; python_version >= '3.9'
 wsproto==1.3.2; python_version >= '3.10'
 zstandard==0.25.0; python_version >= '3.9'
diff --git a/circleci/images/pgupgradetester/files/etc/requirements.txt b/circleci/images/pgupgradetester/files/etc/requirements.txt
index 0c9b89b..c5da543 100644
--- a/circleci/images/pgupgradetester/files/etc/requirements.txt
+++ b/circleci/images/pgupgradetester/files/etc/requirements.txt
@@ -1,4 +1,4 @@
-# generated from Citus's Pipfile.lock (in src/test/regress) as of citusdata/citus#8547
+# generated from Citus's Pipfile.lock (in src/test/regress) as of citusdata/citus#8596
 # using `pipenv requirements > requirements.txt`, so as to avoid the
 # need for pipenv/pyenv in this image
 
@@ -6,19 +6,19 @@
 aioquic==1.2.0; python_version >= '3.8'
 argon2-cffi==25.1.0; python_version >= '3.8'
 argon2-cffi-bindings==25.1.0; python_version >= '3.9'
-asgiref==3.11.0; python_version >= '3.9'
+asgiref==3.11.1; python_version >= '3.9'
 attrs==26.1.0; python_version >= '3.9'
 bcrypt==5.0.0; python_version >= '3.8'
 blinker==1.9.0; python_version >= '3.9'
 brotli==1.2.0
-certifi==2026.2.25; python_version >= '3.7'
+certifi==2026.5.20; python_version >= '3.7'
 cffi==2.0.0; python_version >= '3.9'
-click==8.3.2; python_version >= '3.10'
+click==8.4.1; python_version >= '3.10'
 construct==2.10.70; python_version >= '3.6'
 cryptography==46.0.7; python_version >= '3.8' and python_full_version not in '3.9.0, 3.9.1'
 docopt==0.6.2
 execnet==2.1.2; python_version >= '3.8'
-filelock==3.28.0; python_version >= '3.10'
+filelock==3.29.0; python_version >= '3.10'
 flask==3.1.3; python_version >= '3.9'
 h11==0.16.0; python_version >= '3.8'
 h2==4.3.0; python_version >= '3.9'
@@ -30,24 +30,24 @@ jinja2==3.1.6; python_version >= '3.7'
 kaitaistruct==0.11; python_version >= '2.7' and python_version not in '3.0, 3.1, 3.2, 3.3'
 ldap3==2.9.1
 markupsafe==3.0.3; python_version >= '3.9'
-mitmproxy @ git+https://github.com/citusdata/mitmproxy.git@70bad9a3c098f605e5f8b25553e5db5334018ff1
+mitmproxy @ git+https://github.com/citusdata/mitmproxy.git@df5879516a57ea780e1cc88edaf2051e1d32915f
 mitmproxy-linux==0.12.9; python_version >= '3.12'
 mitmproxy-rs==0.12.9; python_version >= '3.12'
 msgpack==1.1.2; python_version >= '3.9'
-packaging==26.1; python_version >= '3.8'
+packaging==26.2; python_version >= '3.8'
 pluggy==1.6.0; python_version >= '3.9'
-psycopg==3.3.3; python_version >= '3.10'
+psycopg==3.3.4; python_version >= '3.10'
 publicsuffix2==2.20191221
 pyasn1==0.6.3; python_version >= '3.8'
 pyasn1-modules==0.4.2; python_version >= '3.8'
 pycparser==3.0; python_version >= '3.10'
 pygments==2.20.0; python_version >= '3.9'
 pylsqpack==0.3.24; python_version >= '3.10'
-pyopenssl==25.3.0; python_version >= '3.7'
+pyopenssl==26.2.0; python_version >= '3.8'
 pyparsing==3.3.2; python_version >= '3.9'
 pyperclip==1.9.0
 pytest==9.0.3; python_version >= '3.10'
-pytest-asyncio==1.3.0; python_version >= '3.10'
+pytest-asyncio==1.4.0; python_version >= '3.10'
 pytest-repeat==0.9.4; python_version >= '3.9'
 pytest-timeout==2.4.0; python_version >= '3.7'
 pytest-xdist==3.8.0; python_version >= '3.9'
@@ -57,8 +57,8 @@ service-identity==24.2.0; python_version >= '3.8'
 sortedcontainers==2.4.0
 tornado==6.5.5; python_version >= '3.9'
 typing-extensions==4.14.0; python_version >= '3.9'
-urwid==3.0.5; python_full_version >= '3.9.0'
-wcwidth==0.6.0; python_version >= '3.8'
+urwid==4.0.0; python_full_version >= '3.9.0'
+wcwidth==0.7.0; python_version >= '3.8'
 werkzeug==3.1.6; python_version >= '3.9'
 wsproto==1.3.2; python_version >= '3.10'
 zstandard==0.25.0; python_version >= '3.9'
diff --git a/circleci/images/stylechecker/files/etc/requirements.txt b/circleci/images/stylechecker/files/etc/requirements.txt
index bc4d321..72a70b7 100644
--- a/circleci/images/stylechecker/files/etc/requirements.txt
+++ b/circleci/images/stylechecker/files/etc/requirements.txt
@@ -1,19 +1,19 @@
-# generated from Citus's Pipfile.lock (in src/test/regress) as of citusdata/citus#8547
+# generated from Citus's Pipfile.lock (in src/test/regress) as of citusdata/citus#8596
 # using `pipenv requirements --dev-only > requirements.txt`, so as to avoid the
 # need for pipenv/pyenv in this image
 
 -i https://pypi.python.org/simple
 attrs==26.1.0; python_version >= '3.9'
 black==26.3.1; python_version >= '3.10'
-click==8.3.2; python_version >= '3.10'
+click==8.4.1; python_version >= '3.10'
 flake8==7.3.0; python_version >= '3.9'
 flake8-bugbear==25.11.29; python_version >= '3.10'
 isort==8.0.1; python_full_version >= '3.10.0'
 mccabe==0.7.0; python_version >= '3.6'
 mypy-extensions==1.1.0; python_version >= '3.8'
-packaging==26.1; python_version >= '3.8'
-pathspec==1.0.4; python_version >= '3.9'
-platformdirs==4.9.6; python_version >= '3.10'
+packaging==26.2; python_version >= '3.8'
+pathspec==1.1.1; python_version >= '3.9'
+platformdirs==4.10.0; python_version >= '3.10'
 pycodestyle==2.14.0; python_version >= '3.9'
 pyflakes==3.4.0; python_version >= '3.9'
 pytokens==0.4.1; python_version >= '3.8'