diff --git a/net-proxy/privoxy/Manifest b/net-proxy/privoxy/Manifest
index 5d44ae7b96503..d58dcea08d262 100644
--- a/net-proxy/privoxy/Manifest
+++ b/net-proxy/privoxy/Manifest
@@ -1,2 +1,3 @@
 DIST privoxy-3.0.34-stable-src.tar.gz 1589785 BLAKE2B d879d3827dc1e6dd6a3d13ab07b788a235a16dcc4b050f17dd43543c0fad1cf9c9ceb2a0ae1ec3885798db5041a6c1fc2c270befd4d8ecf10254a58533458dba SHA512 f963419ae2cb6dd72cd892fa043768d99a4118792833de2e666d6a800fbe9a7fcb0641f15e3211e0b01a74609c65aeb60af1051f1a19daa1048314599679b685
 DIST privoxy-4.0.0-stable-src.tar.gz 1746840 BLAKE2B 194987c99fb8da78c369b354bae40557a5c6aafb6091df11b2752a013c24c43e56026e7ec51ebe168f200a5bfdf3ee28fa75867dabde8f2d2a525142b4198f2d SHA512 d89b75c486d403ce99bf439d8a5bacf59cc2c43b2acec55eddab24e818be20cfe23954ca01a20efa86c8afb38bea64bb91435b063144fd549a8c7e03a2320000
+DIST privoxy-4.2.0-stable-src.tar.gz 1791064 BLAKE2B fa204d35ca6f70c8e40a97cec561f1772a8b9e790eeb263d26ef4f996d2381306cf5e3e62d6025b58033b72a554f23249c7e46b7c610d179ad4f514e2ea42580 SHA512 e727a16ead5759e3e976d42558ad0c0af137a7f74d8ccc83ed53a34320654362489a77d3bd54c9b4d5b84c5b4ecf8e375d2c1d0e3108eb26acce3014dfbefdb0
diff --git a/net-proxy/privoxy/files/privoxy-4.2.0-gentoo.patch b/net-proxy/privoxy/files/privoxy-4.2.0-gentoo.patch
new file mode 100644
index 0000000000000..94a7723236fa3
--- /dev/null
+++ b/net-proxy/privoxy/files/privoxy-4.2.0-gentoo.patch
@@ -0,0 +1,121 @@
+diff --git a/GNUmakefile.in b/GNUmakefile.in
+index 214a8e1..45ca660 100644
+--- a/GNUmakefile.in
++++ b/GNUmakefile.in
+@@ -64,8 +64,8 @@ MAN_DEST     = $(MAN_DIR)/man8
+ PRIVOXY_TOOL_MAN_DEST = $(MAN_DIR)/man1
+ PRIVOXY_MAN_PAGE = privoxy.8
+ SHARE_DEST   = @datadir@
+-DOC_DEST     = $(SHARE_DEST)/doc/privoxy
+-VAR_DEST     = @localstatedir@
++DOC_DEST     = @docdir@
++VAR_DEST     = /var
+ LOGS_DEST    = $(VAR_DEST)/log/privoxy
+ PIDS_DEST    = $(VAR_DEST)/run
+ 
+@@ -902,8 +902,6 @@ install: CONF_DEST LOG_DEST PID_DEST check_doc GROUP_T
+ 		$(INSTALL) $(INSTALL_T) $(DOK_WEB)/man-page/*html $(DESTDIR)$$DOC/man-page;\
+ 		$(INSTALL) $(INSTALL_T) $(DOK_WEB)/privoxy-index.html $(DESTDIR)$$DOC/index.html;\
+ 		$(INSTALL) $(INSTALL_T) AUTHORS $(DESTDIR)$$DOC;\
+-		$(INSTALL) $(INSTALL_T) LICENSE $(DESTDIR)$$DOC;\
+-		$(INSTALL) $(INSTALL_T) LICENSE.GPLv3 $(DESTDIR)$$DOC;\
+ 		$(INSTALL) $(INSTALL_T) README $(DESTDIR)$$DOC;\
+ 		$(INSTALL) $(INSTALL_T) ChangeLog $(DESTDIR)$$DOC;\
+ 		$(INSTALL) $(INSTALL_T) $(DOK_WEB)/p_doc.css $(DESTDIR)$$DOC;\
+@@ -986,34 +984,8 @@ install: CONF_DEST LOG_DEST PID_DEST check_doc GROUP_T
+ 	fi ;\
+ 	$(ECHO) Installing configuration files to $(DESTDIR)$(CONF_DEST);\
+ 	for i in $(CONFIGS); do \
+-		if [ "$$i" = "default.action" ] || [ "$$i" = "default.filter" ] ; then \
+-			$(RM) $(DESTDIR)$(CONF_DEST)/$$i ;\
+-			$(ECHO) Installing fresh $$i;\
+ 			$(INSTALL) $$INSTALL_CONF $$i $(DESTDIR)$(CONF_DEST) || exit 1;\
+-		elif [ -s "$(DESTDIR)$(CONF_DEST)/$$i" ]; then \
+-			$(ECHO) Installing $$i as $$i.new ;\
+-			$(INSTALL) $$INSTALL_CONF $$i $(DESTDIR)$(CONF_DEST)/$$i.new || exit 1;\
+-			NEW=1;\
+-		else \
+-			$(INSTALL) $$INSTALL_CONF $$i $(DESTDIR)$(CONF_DEST) || exit 1;\
+-		fi ;\
+ 	done ;\
+-	if [ -n "$$NEW" ]; then \
+-		$(CHMOD) $(RWD_MODE) $(DESTDIR)$(CONF_DEST)/*.new || exit 1 ;\
+-		$(ECHO) "Warning: Older config files are preserved. Check new versions for changes!" ;\
+-	fi ;\
+-	[ ! -f $(DESTDIR)$(LOG_DEST)/logfile ] && $(ECHO) Creating logfiles in $(DESTDIR)$(LOG_DEST) || \
+-		$(ECHO) Checking logfiles in $(DESTDIR)$(LOG_DEST) ;\
+-		$(TOUCH) $(DESTDIR)$(LOG_DEST)/logfile || exit 1 ;\
+-	if [ x$$USER != x ]; then \
+-		$(CHOWN) $$USER $(DESTDIR)$(LOG_DEST)/logfile || \
+-		$(ECHO) "** WARNING ** current install user different from configured user. Logging may fail!!" ;\
+-	fi ;\
+-	if [ x$$GROUP_T != x ]; then \
+-		$(CHGRP) $$GROUP_T $(DESTDIR)$(LOG_DEST)/logfile || \
+-		$(ECHO) "** WARNING ** current install user different from configured user. Logging may fail!!" ;\
+-	fi ;\
+-	$(CHMOD) $(RWD_MODE) $(DESTDIR)$(LOG_DEST)/logfile || exit 1 ;\
+ 	if [ "$(prefix)" = "/usr/local" ] || [ "$(prefix)" = "/usr" ]; then \
+ 		if [ -f /etc/slackware-version ] && [ -d /etc/rc.d/ ] && [ -w /etc/rc.d/ ] ; then \
+                $(SED) 's+%PROGRAM%+$(PROGRAM)+' slackware/rc.privoxy.in | \
+diff --git a/config b/config
+index d24d910..71ce49f 100644
+--- a/config
++++ b/config
+@@ -259,7 +259,7 @@
+ #
+ #      No trailing "/", please.
+ #
+-confdir .
++confdir /etc/privoxy
+ #
+ #  2.2. templdir
+ #  ==============
+@@ -344,7 +344,7 @@ confdir .
+ #
+ #      No trailing "/", please.
+ #
+-logdir .
++logdir /var/log/privoxy
+ #
+ #  2.5. actionsfile
+ #  =================
+@@ -478,7 +478,7 @@ filterfile user.filter      # User customizations
+ #      require additional software to do it. For details, please
+ #      refer to the documentation for your operating system.
+ #
+-logfile logfile
++logfile privoxy.log
+ #
+ #  2.8. trustfile
+ #  ===============
+diff --git a/default.action.master b/default.action.master
+index a65de1c..8502188 100644
+--- a/default.action.master
++++ b/default.action.master
+@@ -557,7 +557,7 @@ allow-ads   = -block -filter{banners-by-size} -filter{banners-by-link}
+ +client-header-tagger{range-requests} \
+ +hide-from-header{block} \
+ +server-header-tagger{content-type} \
+-+set-image-blocker{pattern} \
+++set-image-blocker{blank} \
+ }
+ standard.Cautious
+ 
+@@ -580,7 +580,7 @@ standard.Cautious
+ +hide-referrer{conditional-block} \
+ +server-header-tagger{content-type} \
+ +session-cookies-only \
+-+set-image-blocker{pattern} \
+++set-image-blocker{blank} \
+ }
+ standard.Medium
+ 
+@@ -621,7 +621,7 @@ standard.Medium
+ +limit-connect{,} \
+ +overwrite-last-modified{randomize} \
+ +server-header-tagger{content-type} \
+-+set-image-blocker{pattern} \
+++set-image-blocker{blank} \
+ }
+ standard.Advanced
+ 
diff --git a/net-proxy/privoxy/privoxy-4.2.0.ebuild b/net-proxy/privoxy/privoxy-4.2.0.ebuild
new file mode 100644
index 0000000000000..edfc5e15001a8
--- /dev/null
+++ b/net-proxy/privoxy/privoxy-4.2.0.ebuild
@@ -0,0 +1,159 @@
+# Copyright 1999-2026 Gentoo Authors
+# Distributed under the terms of the GNU General Public License v2
+
+EAPI=8
+
+inherit autotools systemd toolchain-funcs
+
+[ "${PV##*_}" = "beta" ] &&
+	PRIVOXY_STATUS="beta" ||
+	PRIVOXY_STATUS="stable"
+
+DESCRIPTION="A web proxy with advanced filtering capabilities for enhancing privacy"
+HOMEPAGE="https://www.privoxy.org https://sourceforge.net/projects/ijbswa/"
+SRC_URI="https://downloads.sourceforge.net/ijbswa/${P%_*}-${PRIVOXY_STATUS}-src.tar.gz"
+
+S="${WORKDIR}/${P%_*}-${PRIVOXY_STATUS}"
+
+LICENSE="GPL-2+"
+SLOT="0"
+KEYWORDS="~alpha ~amd64 ~arm ~arm64 ~ppc ~ppc64 ~riscv ~sparc ~x86"
+IUSE="+acl brotli client-tags compression editor extended-host-patterns
+extended-statistics external-filters +fast-redirects +force fuzz
+graceful-termination +image-blocking ipv6 +jit lfs mbedtls +openssl
+png-images sanitize selinux ssl +stats +threads toggle tools whitelists
++zlib +zstd"
+
+DEPEND="
+	acct-group/privoxy
+	acct-user/privoxy
+	dev-libs/libpcre2
+	brotli? ( app-arch/brotli )
+	ssl? (
+		mbedtls? ( net-libs/mbedtls:3= )
+		openssl? ( dev-libs/openssl:= )
+	)
+	zlib? ( virtual/zlib:= )
+	zstd? ( app-arch/zstd )
+"
+RDEPEND="${DEPEND}
+	extended-host-patterns? ( dev-lang/perl )
+	selinux? ( sec-policy/selinux-privoxy )
+	tools? (
+		net-misc/curl
+		dev-lang/perl
+	)
+"
+REQUIRED_USE="
+	brotli? ( zlib )
+	client-tags? ( threads )
+	compression? ( zlib )
+	extended-statistics? ( threads )
+	fuzz? ( zlib )
+	ssl? ( ^^ ( mbedtls openssl ) threads )
+	toggle? ( editor )
+"
+
+PATCHES=(
+	"${FILESDIR}"/${PN}-4.2.0-gentoo.patch
+	"${FILESDIR}"/${PN}-3.0.28-strip.patch
+)
+
+pkg_pretend() {
+	if ! use threads; then
+		ewarn
+		ewarn "Privoxy may be very slow without threads support, consider enabling it."
+		ewarn "See also https://www.privoxy.org/faq/trouble.html#GENTOO-RICERS"
+		ewarn "Additionally some features may not build or work poperly. You are on your own."
+		ewarn
+	fi
+}
+
+src_prepare() {
+	default
+	mv configure.in configure.ac || die
+	sed -i "s|/p\.p/|/config.privoxy.org/|g" tools/privoxy-regression-test.pl || die
+
+	# autoreconf needs to be called even if we don't modify any autotools source files
+	# See main makefile
+	eautoreconf
+}
+
+src_configure() {
+	local myconf="--without-mbedtls --without-openssl"
+	if use ssl; then
+		myconf="$(use_with mbedtls) $(use_with openssl)"
+	fi
+	if use sanitize; then
+		myconf+=" --with-usan"
+		# msan is available in clang only
+		# asan is broken with current configure tests in gcc
+		tc-is-clang && myconf+=" --with-msan --with-asan"
+	fi
+
+	# --with-debug only enables debug CFLAGS
+	# --with-docbook and --with-db2html and their deps are useless,
+	#	since docs are already pregenerated in the source tarball
+	econf \
+		--sysconfdir=/etc/privoxy \
+		--disable-accept-filter \
+		--enable-dynamic-pcre \
+		--without-assertions \
+		--with-user=privoxy \
+		--with-group=privoxy \
+		$(use_enable acl acl-support) \
+		$(use_enable compression) \
+		$(use_enable client-tags) \
+		$(use_enable editor) \
+		$(use_enable extended-host-patterns pcre-host-patterns) \
+		$(use_enable extended-statistics) \
+		$(use_enable fast-redirects) \
+		$(use_enable force) \
+		$(use_enable fuzz) \
+		$(use_enable graceful-termination) \
+		$(use_enable image-blocking) \
+		$(use_enable jit pcre-jit-compilation) \
+		$(use_enable ipv6 ipv6-support) \
+		$(use_enable lfs large-file-support) \
+		$(use_enable png-images no-gifs) \
+		$(use_enable stats) \
+		$(use_enable threads pthread) \
+		$(use_enable toggle) \
+		$(use_enable whitelists trust-files) \
+		$(use_enable zlib) \
+		$(use_with brotli) \
+		$(use_with zstd) \
+		${myconf}
+}
+
+src_install() {
+	default
+
+	newinitd "${FILESDIR}/privoxy.initd-3" privoxy
+	systemd_dounit "${FILESDIR}"/${PN}.service
+
+	insinto /etc/logrotate.d
+	newins "${FILESDIR}/privoxy.logrotate" privoxy
+
+	diropts -m 0750 -g privoxy -o privoxy
+	keepdir /var/log/privoxy
+
+	use extended-host-patterns && newbin tools/url-pattern-translator.pl privoxy-url-pattern-translator.pl
+	if use tools; then
+		dobin tools/{privoxy-log-parser.pl,privoxy-regression-test.pl}
+		newbin tools/uagen.pl privoxy-uagen.pl
+	fi
+
+	rmdir "${ED}/var/run" || die
+	chown privoxy:root "${ED}/etc/privoxy" || die
+}
+
+pkg_postinst() {
+	if use extended-host-patterns; then
+		ewarn
+		ewarn "You enabled extended-host-patterns, now you *must* convert all action files in"
+		ewarn "PCRE-compatible format, or privoxy will fail to start. Helper tool"
+		ewarn "privoxy-url-pattern-translator.pl is available."
+		ewarn
+	fi
+}