diff --git a/Makefile b/Makefile
index 0148bfdeaa..31af902b30 100644
--- a/Makefile
+++ b/Makefile
@@ -77,7 +77,7 @@ RECEPTOR_IMAGE ?= quay.io/ansible/receptor:devel
 SRC_ONLY_PKGS ?= cffi,pycparser,psycopg,twilio
 # These should be upgraded in the AWX and Ansible venv before attempting
 # to install the actual requirements
-VENV_BOOTSTRAP ?= pip==21.2.4 setuptools==78.1.1 setuptools_scm[toml]==8.0.4 wheel==0.42.0 cython==0.29.37
+VENV_BOOTSTRAP ?= pip==21.2.4 setuptools==78.1.1 setuptools_scm[toml]==8.0.4 wheel==0.42.0 cython==3.1.3
 
 NAME ?= awx
 
diff --git a/licenses/docutils.txt b/licenses/docutils.txt
deleted file mode 100644
index ec5b3bd729..0000000000
--- a/licenses/docutils.txt
+++ /dev/null
@@ -1,137 +0,0 @@
-==================
- Copying Docutils
-==================
-
-:Author: David Goodger
-:Contact: goodger@python.org
-:Date: $Date: 2015-05-08 17:56:32 +0200 (Fr, 08 Mai 2015) $
-:Web site: http://docutils.sourceforge.net/
-:Copyright: This document has been placed in the public domain.
-
-Most of the files included in this project have been placed in the
-public domain, and therefore have no license requirements and no
-restrictions on copying or usage; see the `Public Domain Dedication`_
-below.  There are a few exceptions_, listed below.
-Files in the Sandbox_ are not distributed with Docutils releases and
-may have different license terms.
-
-
-Public Domain Dedication
-========================
-
-The persons who have associated their work with this project (the
-"Dedicator": David Goodger and the many contributors to the Docutils
-project) hereby dedicate the entire copyright, less the exceptions_
-listed below, in the work of authorship known as "Docutils" identified
-below (the "Work") to the public domain.
-
-The primary repository for the Work is the Internet World Wide Web
-site <http://docutils.sourceforge.net/>.  The Work consists of the
-files within the "docutils" module of the Docutils project Subversion
-repository (Internet host docutils.svn.sourceforge.net, filesystem path
-/svnroot/docutils), whose Internet web interface is located at
-<http://docutils.svn.sourceforge.net/viewvc/docutils/>.  Files dedicated to the
-public domain may be identified by the inclusion, near the beginning
-of each file, of a declaration of the form::
-
-    Copyright: This document/module/DTD/stylesheet/file/etc. has been
-               placed in the public domain.
-
-Dedicator makes this dedication for the benefit of the public at large
-and to the detriment of Dedicator's heirs and successors.  Dedicator
-intends this dedication to be an overt act of relinquishment in
-perpetuity of all present and future rights under copyright law,
-whether vested or contingent, in the Work.  Dedicator understands that
-such relinquishment of all rights includes the relinquishment of all
-rights to enforce (by lawsuit or otherwise) those copyrights in the
-Work.
-
-Dedicator recognizes that, once placed in the public domain, the Work
-may be freely reproduced, distributed, transmitted, used, modified,
-built upon, or otherwise exploited by anyone for any purpose,
-commercial or non-commercial, and in any way, including by methods
-that have not yet been invented or conceived.
-
-(This dedication is derived from the text of the `Creative Commons
-Public Domain Dedication`. [#]_)
-
-.. [#] Creative Commons has `retired this legal tool`__ and does not
-   recommend that it be applied to works: This tool is based on United
-   States law and may not be applicable outside the US. For dedicating new
-   works to the public domain, Creative Commons recommend the replacement
-   Public Domain Dedication CC0_ (CC zero, "No Rights Reserved"). So does
-   the Free Software Foundation in its license-list_.
-
-   __  http://creativecommons.org/retiredlicenses
-   .. _CC0: http://creativecommons.org/about/cc0
-
-Exceptions
-==========
-
-The exceptions to the `Public Domain Dedication`_ above are:
-
-* docutils/writers/s5_html/themes/default/iepngfix.htc:
-
-      IE5.5+ PNG Alpha Fix v1.0 by Angus Turnbull
-      <http://www.twinhelix.com>.  Free usage permitted as long as
-      this notice remains intact.
-
-* docutils/utils/math/__init__.py,
-  docutils/utils/math/latex2mathml.py,
-  docutils/writers/xetex/__init__.py,
-  docutils/writers/latex2e/docutils-05-compat.sty,
-  docs/user/docutils-05-compat.sty.txt,
-  docutils/utils/error_reporting.py,
-  docutils/test/transforms/test_smartquotes.py:
-
-  Copyright © Günter Milde.
-  Released under the terms of the `2-Clause BSD license`_
-  (`local copy <licenses/BSD-2-Clause.txt>`__).
-
-* docutils/utils/smartquotes.py
-
-  Copyright © 2011 Günter Milde,
-  based on `SmartyPants`_ © 2003 John Gruber
-  (released under a 3-Clause BSD license included in the file)
-  and smartypants.py © 2004, 2007 Chad Miller.
-  Released under the terms of the `2-Clause BSD license`_
-  (`local copy <licenses/BSD-2-Clause.txt>`__).
-
-  .. _SmartyPants: http://daringfireball.net/projects/smartypants/
-
-* docutils/utils/math/math2html.py,
-  docutils/writers/html4css1/math.css
-
-  Copyright © Alex Fernández
-  These files are part of eLyXer_, released under the `GNU
-  General Public License`_ version 3 or later. The author relicensed
-  them for Docutils under the terms of the `2-Clause BSD license`_
-  (`local copy <licenses/BSD-2-Clause.txt>`__).
-
-  .. _eLyXer: http://www.nongnu.org/elyxer/
-
-* docutils/utils/roman.py, copyright by Mark Pilgrim, released under the
-  `Python 2.1.1 license`_ (`local copy`__).
-
-  __ licenses/python-2-1-1.txt
-
-* tools/editors/emacs/rst.el, copyright by Free Software Foundation,
-  Inc., released under the `GNU General Public License`_ version 3 or
-  later (`local copy`__).
-
-  __ licenses/gpl-3-0.txt
-
-The `2-Clause BSD license`_ and the Python licenses are OSI-approved_
-and GPL-compatible_.
-
-Plaintext versions of all the linked-to licenses are provided in the
-licenses_ directory.
-
-.. _sandbox: http://docutils.sourceforge.net/sandbox/README.html
-.. _licenses: licenses/
-.. _Python 2.1.1 license: http://www.python.org/2.1.1/license.html
-.. _GNU General Public License: http://www.gnu.org/copyleft/gpl.html
-.. _2-Clause BSD license: http://www.spdx.org/licenses/BSD-2-Clause
-.. _OSI-approved: http://opensource.org/licenses/
-.. _license-list:
-.. _GPL-compatible: http://www.gnu.org/licenses/license-list.html
diff --git a/requirements/requirements.in b/requirements/requirements.in
index 28e0197cde..48dc040a42 100644
--- a/requirements/requirements.in
+++ b/requirements/requirements.in
@@ -2,7 +2,7 @@ aiohttp>=3.11.6 # CVE-2024-52304
 ansiconv==1.0.0  # UPGRADE BLOCKER: from 2013, consider replacing instead of upgrading
 ansible-runner==2.4.1
 jq  # used for indirect host counting feature
-asciichartpy
+asciichartpy<=1.5.7 # Unable to build from source for >1.5.7 due to missing README.md in PyPI sdist
 asn1
 azure-identity
 azure-keyvault
@@ -10,8 +10,8 @@ boto3
 botocore
 channels
 channels-redis
-cryptography>=41.0.7  # CVE-2023-49083
-Cython<3 # due to https://github.com/yaml/pyyaml/pull/702
+cryptography>=42.0.4  # CVE-2024-26130
+Cython
 daphne
 distro
 django==4.2.23  # CVE-2025-48432
@@ -37,7 +37,7 @@ JSON-log-formatter
 jsonschema
 Markdown  # used for formatting API help
 maturin  # pydantic-core build dep
-msgpack<1.0.6  # 1.0.6+ requires cython>=3
+msgpack
 msrestazure
 OPA-python-client==2.0.2 # Code contain monkey patch targeted to 2.0.2 to fix https://github.com/Turall/OPA-python-client/issues/29
 openshift
@@ -53,11 +53,11 @@ pygerduty
 PyGithub <= 2.6.0
 pyopenssl>=23.2.0  # resolve dep conflict from cryptography pin above
 pyparsing==2.4.6  # Upgrading to v3 of pyparsing introduce errors on smart host filtering: Expected 'or' term, found 'or'  (at char 15), (line:1, col:16)
-python-daemon>3.0.0
+python-daemon
 python-dsv-sdk>=1.0.4
 python-tss-sdk>=1.2.1
 python-ldap
-pyyaml>=6.0.1
+pyyaml>=6.0.2
 pyzstd  # otel collector log file compression library
 receptorctl==1.5.7
 social-auth-core == 4.5.4 # hard pinned due to resolver picking CVE version when uncapped
@@ -78,6 +78,8 @@ setuptools_scm[toml]  # see UPGRADE BLOCKERs, xmlsec build dep
 setuptools-rust>=0.11.4  # cryptography build dep
 pkgconfig>=1.5.1  # xmlsec build dep - needed for offline build
 django-flags>=5.0.13
+protobuf>=4.25.8 # CVE-2025-4565
+idna>=3.10 # CVE-2024-3651
 # Temporarily added to use ansible-runner from git branch, to be removed
 # when ansible-runner moves from requirements_git.txt to here
 pbr
diff --git a/requirements/requirements.txt b/requirements/requirements.txt
index e2a9f964dd..48089cea5e 100644
--- a/requirements/requirements.txt
+++ b/requirements/requirements.txt
@@ -22,7 +22,7 @@ ansible-runner==2.4.1
     # via -r /awx_devel/requirements/requirements.in
 ansiconv==1.0.0
     # via -r /awx_devel/requirements/requirements.in
-asciichartpy==1.5.25
+asciichartpy==1.5.7
     # via -r /awx_devel/requirements/requirements.in
 asgiref==3.7.2
     # via
@@ -30,6 +30,7 @@ asgiref==3.7.2
     #   channels-redis
     #   daphne
     #   django
+    #   django-ansible-base
     #   django-cors-headers
 asn1==2.7.0
     # via -r /awx_devel/requirements/requirements.in
@@ -106,7 +107,7 @@ click==8.1.7
     # via receptorctl
 constantly==23.10.4
     # via twisted
-cryptography==41.0.7
+cryptography==42.0.8
     # via
     #   -r /awx_devel/requirements/requirements.in
     #   adal
@@ -120,7 +121,7 @@ cryptography==41.0.7
     #   pyopenssl
     #   service-identity
     #   social-auth-core
-cython==0.29.37
+cython==3.1.3
     # via -r /awx_devel/requirements/requirements.in
 daphne==3.0.2
     # via
@@ -187,8 +188,6 @@ djangorestframework==3.15.2
     #   django-ansible-base
 djangorestframework-yaml==2.0.0
     # via -r /awx_devel/requirements/requirements.in
-docutils==0.20.1
-    # via python-daemon
 dynaconf==3.2.10
     # via
     #   -r /awx_devel/requirements/requirements.in
@@ -221,8 +220,9 @@ hyperlink==21.0.0
     # via
     #   autobahn
     #   twisted
-idna==3.6
+idna==3.10
     # via
+    #   -r /awx_devel/requirements/requirements.in
     #   hyperlink
     #   requests
     #   twisted
@@ -305,7 +305,7 @@ msal==1.26.0
     #   msal-extensions
 msal-extensions==1.1.0
     # via azure-identity
-msgpack==1.0.5
+msgpack==1.1.1
     # via
     #   -r /awx_devel/requirements/requirements.in
     #   channels-redis
@@ -363,7 +363,7 @@ opentelemetry-sdk==1.24.0
     #   opentelemetry-exporter-otlp-proto-http
 opentelemetry-semantic-conventions==0.45b0
     # via opentelemetry-sdk
-packaging==23.2
+packaging==25.0
     # via
     #   ansible-runner
     #   msal-extensions
@@ -384,8 +384,9 @@ propcache==0.2.0
     # via
     #   aiohttp
     #   yarl
-protobuf==4.25.3
+protobuf==4.25.8
     # via
+    #   -r /awx_devel/requirements/requirements.in
     #   googleapis-common-protos
     #   opentelemetry-proto
 psutil==5.9.8
@@ -420,6 +421,7 @@ pygithub==2.6.0
 pyjwt[crypto]==2.8.0
     # via
     #   adal
+    #   django-ansible-base
     #   msal
     #   pygithub
     #   social-auth-core
@@ -434,7 +436,7 @@ pyparsing==2.4.6
     # via -r /awx_devel/requirements/requirements.in
 pyrad==2.4
     # via django-radius
-python-daemon==3.0.1
+python-daemon==3.1.2
     # via
     #   -r /awx_devel/requirements/requirements.in
     #   ansible-runner
@@ -461,7 +463,7 @@ pytz==2024.1
     # via
     #   irc
     #   tempora
-pyyaml==6.0.1
+pyyaml==6.0.2
     # via
     #   -r /awx_devel/requirements/requirements.in
     #   ansible-runner
@@ -485,6 +487,7 @@ requests==2.32.3
     #   -r /awx_devel/requirements/requirements.in
     #   adal
     #   azure-core
+    #   django-ansible-base
     #   django-oauth-toolkit
     #   kubernetes
     #   msal
@@ -551,7 +554,7 @@ tempora==5.5.1
     # via
     #   irc
     #   jaraco-logging
-tomli==2.0.1
+tomli==2.2.1
     # via
     #   incremental
     #   maturin
@@ -585,6 +588,7 @@ urllib3==1.26.20
     # via
     #   -r /awx_devel/requirements/requirements.in
     #   botocore
+    #   django-ansible-base
     #   kubernetes
     #   pygithub
     #   requests
@@ -619,7 +623,6 @@ setuptools==78.1.1
     #   autobahn
     #   incremental
     #   opentelemetry-instrumentation
-    #   python-daemon
     #   setuptools-rust
     #   setuptools-scm
     #   zope-interface