diff --git a/sysutils/amazon-ssm-agent/Makefile b/sysutils/amazon-ssm-agent/Makefile
index 0fc078d5c8fb..d6caed0bb2f6 100644
--- a/sysutils/amazon-ssm-agent/Makefile
+++ b/sysutils/amazon-ssm-agent/Makefile
@@ -1,59 +1,57 @@
 PORTNAME=	amazon-ssm-agent
-PORTVERSION=	2.3.1205.0
-PORTREVISION=	41
+PORTVERSION=	3.3.4177.0
+PORTREVISION=	0
 CATEGORIES=	sysutils
 
 MAINTAINER=	cperciva@FreeBSD.org
 COMMENT=	Amazon Simple Systems Manager Agent
 WWW=		https://github.com/aws/amazon-ssm-agent
 
 LICENSE=	APACHE20
 LICENSE_FILE=	${WRKSRC}/LICENSE
 
 RUN_DEPENDS=	${LOCALBASE}/share/certs/ca-root-nss.crt:security/ca_root_nss
 
 USES=		go
 
 USE_GITHUB=	yes
 GH_ACCOUNT=	aws
 GH_SUBDIR=	src/github.com/aws/amazon-ssm-agent
-GH_TUPLE=	creack:pty:v1.1.18:pty \
-		golang:sys:v0.6.0:sys
+GH_TUPLE=	creack:pty:v1.1.18:pty
 
 GO_BUILDFLAGS=	-ldflags "-s -w"
-GO_TARGET=	./agent:${PREFIX}/sbin/amazon-ssm-agent \
+GO_TARGET=	./agent:${PREFIX}/sbin/ssm-agent-worker \
+		./core:${PREFIX}/sbin/amazon-ssm-agent \
 		./agent/framework/processor/executer/outofproc/worker:${PREFIX}/sbin/ssm-document-worker \
 		./agent/framework/processor/executer/outofproc/sessionworker:${PREFIX}/sbin/ssm-session-worker \
 		./agent/session/logging:${PREFIX}/sbin/ssm-session-logger \
-		./agent/cli-main:${PREFIX}/sbin/ssm-cli
+		./agent/cli-main:${PREFIX}/sbin/ssm-cli \
+		./agent/setupcli:${PREFIX}/sbin/ssm-setup-cli
 
 PLIST_FILES=	etc/amazon/ssm/amazon-ssm-agent.json.template	\
 		etc/amazon/ssm/seelog_unix.xml.template		\
 		sbin/amazon-ssm-agent				\
+		sbin/ssm-agent-worker				\
 		sbin/ssm-document-worker			\
 		sbin/ssm-session-worker				\
 		sbin/ssm-session-logger				\
-		sbin/ssm-cli
+		sbin/ssm-cli					\
+		sbin/ssm-setup-cli
 
 USE_RC_SUBR=	amazon-ssm-agent
 
-pre-patch:
-	${MKDIR} ${WRKSRC}/vendor/src/github.com/creack
-	${LN} -s ${WRKSRC_pty} ${WRKSRC}/vendor/src/github.com/creack/pty
-	${RM} -r ${WRKSRC}/vendor/src/golang.org/x/sys
-	${LN} -s ${WRKSRC_sys} ${WRKSRC}/vendor/src/golang.org/x/sys
-
 post-patch:
 	${LN} -s ${WRKSRC}/vendor/src/* ${WRKSRC}/vendor/
 
 pre-build:
 # set package version
-	cd ${GO_WRKSRC} && BRAZIL_PACKAGE_VERSION=${PORTVERSION} \
-	${SETENV} ${MAKE_ENV} ${GO_ENV} ${GO_CMD} run ./agent/version/versiongenerator/version-gen.go
+	echo "${PORTVERSION}" > "${GO_WRKSRC}/VERSION"
+	cd ${GO_WRKSRC} && \
+		${SETENV} ${MAKE_ENV} ${GO_ENV} ${GO_CMD} run ./agent/version/versiongenerator/version-gen.go
 
 post-install:
 	${MKDIR} ${STAGEDIR}${PREFIX}/etc/amazon/ssm
 	${INSTALL_DATA} ${WRKSRC}/amazon-ssm-agent.json.template ${STAGEDIR}${PREFIX}/etc/amazon/ssm
 	${INSTALL_DATA} ${WRKSRC}/seelog_unix.xml ${STAGEDIR}${PREFIX}/etc/amazon/ssm/seelog_unix.xml.template
 
 .include <bsd.port.mk>
diff --git a/sysutils/amazon-ssm-agent/distinfo b/sysutils/amazon-ssm-agent/distinfo
index 250f703605ed..208f7382a467 100644
--- a/sysutils/amazon-ssm-agent/distinfo
+++ b/sysutils/amazon-ssm-agent/distinfo
@@ -1,7 +1,5 @@
-TIMESTAMP = 1680307376
-SHA256 (aws-amazon-ssm-agent-2.3.1205.0_GH0.tar.gz) = 3a2424c6cd669486581ccf09cd57cbaecd69ef5731a62a50a826eb4b9515face
-SIZE (aws-amazon-ssm-agent-2.3.1205.0_GH0.tar.gz) = 22202960
+TIMESTAMP = 1776697806
+SHA256 (aws-amazon-ssm-agent-3.3.4177.0_GH0.tar.gz) = 1b22af93c2845a6b8324eb7b7568dcf335a7296d1aec9470c7da5f1102dba6ca
+SIZE (aws-amazon-ssm-agent-3.3.4177.0_GH0.tar.gz) = 32185818
 SHA256 (creack-pty-v1.1.18_GH0.tar.gz) = 7a1d6775e3f99b98e5d87303e9aeacfd73d810abffc17e42a561d0650adc980e
 SIZE (creack-pty-v1.1.18_GH0.tar.gz) = 10668
-SHA256 (golang-sys-v0.6.0_GH0.tar.gz) = b4f6d17c7a128f76169964b437cb66b3f2dbf9a33361928ec19dfecf7b03fc54
-SIZE (golang-sys-v0.6.0_GH0.tar.gz) = 1434234
diff --git a/sysutils/amazon-ssm-agent/files/patch-agent_appconfig_constants__unix.go b/sysutils/amazon-ssm-agent/files/patch-agent_appconfig_constants__unix.go
index 6749e1ab546f..2b208b278148 100644
--- a/sysutils/amazon-ssm-agent/files/patch-agent_appconfig_constants__unix.go
+++ b/sysutils/amazon-ssm-agent/files/patch-agent_appconfig_constants__unix.go
@@ -1,20 +1,36 @@
---- agent/appconfig/constants_unix.go.orig	2019-05-08 20:19:03 UTC
+--- agent/appconfig/constants_unix.go.orig	2025-12-22 20:08:01 UTC
 +++ agent/appconfig/constants_unix.go
-@@ -53,7 +53,7 @@ const (
- 	DownloadRoot = "/var/log/amazon/ssm/download/"
+@@ -29,7 +29,7 @@ var (
+ var (
  
- 	// DefaultDataStorePath represents the directory for storing system data
--	DefaultDataStorePath = "/var/lib/amazon/ssm/"
-+	DefaultDataStorePath = "/var/run/amazon/ssm/"
+ 	// AgentExtensions specified the root folder for various kinds of downloaded content
+-	AgentData = "/var/lib/amazon/ssm/"
++	AgentData = "/var/run/amazon/ssm/"
+ 
+ 	// PackageRoot specifies the directory under which packages will be downloaded and installed
+ 	PackageRoot = AgentData + "packages"
+@@ -62,10 +62,10 @@ var (
+ 	DefaultDataStorePath = AgentData
  
  	// EC2ConfigDataStorePath represents the directory for storing ec2 config data
- 	EC2ConfigDataStorePath = "/var/lib/amazon/ec2config/"
-@@ -95,7 +95,7 @@ const (
+-	EC2ConfigDataStorePath = "/var/lib/amazon/ec2config/"
++	EC2ConfigDataStorePath = "/var/run/amazon/ec2config/"
+ 
+ 	// EC2ConfigSettingPath represents the directory for storing ec2 config settings
+-	EC2ConfigSettingPath = "/var/lib/amazon/ec2configservice/"
++	EC2ConfigSettingPath = "/var/run/amazon/ec2configservice/"
+ 
+ 	// UpdaterArtifactsRoot represents the directory for storing update related information
+ 	UpdaterArtifactsRoot = AgentData + "update/"
+@@ -120,9 +120,9 @@ var PowerShellPluginCommandName string
  var PowerShellPluginCommandName string
  
  // DefaultProgramFolder is the default folder for SSM
 -var DefaultProgramFolder = "/etc/amazon/ssm/"
 +var DefaultProgramFolder = "/usr/local/etc/amazon/ssm/"
- var DefaultDocumentWorker = "/usr/bin/ssm-document-worker"
- var DefaultSessionWorker = "/usr/bin/ssm-session-worker"
- var DefaultSessionLogger = "/usr/bin/ssm-session-logger"
+ 
+-var defaultWorkerPath = "/usr/bin/"
++var defaultWorkerPath = "/usr/local/sbin/"
+ var DefaultSSMAgentBinaryPath = defaultWorkerPath + "amazon-ssm-agent"
+ var DefaultSSMAgentWorker = defaultWorkerPath + "ssm-agent-worker"
+ var DefaultDocumentWorker = defaultWorkerPath + "ssm-document-worker"
diff --git a/sysutils/amazon-ssm-agent/files/patch-agent_log_log__unix.go b/sysutils/amazon-ssm-agent/files/patch-agent_log_log__unix.go
deleted file mode 100644
index e45b33f69713..000000000000
--- a/sysutils/amazon-ssm-agent/files/patch-agent_log_log__unix.go
+++ /dev/null
@@ -1,11 +0,0 @@
---- agent/log/log_unix.go.orig	2019-05-08 20:19:03 UTC
-+++ agent/log/log_unix.go
-@@ -24,7 +24,7 @@ const (
- 	// DefaultSeelogConfigFilePath specifies the default seelog location
- 	// The underlying logger is based of https://github.com/cihub/seelog
- 	// See Seelog documentation to customize the logger
--	DefaultSeelogConfigFilePath = "/etc/amazon/ssm/seelog.xml"
-+	DefaultSeelogConfigFilePath = "/usr/local/etc/amazon/ssm/seelog.xml"
- 
- 	DefaultLogDir = "/var/log/amazon/ssm"
- )
diff --git a/sysutils/amazon-ssm-agent/files/patch-agent_plugins_inventory_gatherers_application_dataProvider.go b/sysutils/amazon-ssm-agent/files/patch-agent_plugins_inventory_gatherers_application_dataProvider.go
deleted file mode 100644
index ba93cdd13826..000000000000
--- a/sysutils/amazon-ssm-agent/files/patch-agent_plugins_inventory_gatherers_application_dataProvider.go
+++ /dev/null
@@ -1,10 +0,0 @@
---- agent/plugins/inventory/gatherers/application/dataProvider.go.orig	2020-05-07 19:53:12 UTC
-+++ agent/plugins/inventory/gatherers/application/dataProvider.go
-@@ -7,7 +7,6 @@ import (
- 	"fmt"
- 
- 	"github.com/aws/amazon-ssm-agent/agent/context"
--	"github.com/aws/amazon-ssm-agent/agent/plugins/configurepackage/localpackages"
- 	"github.com/aws/amazon-ssm-agent/agent/plugins/inventory/model"
- )
- 
diff --git a/sysutils/amazon-ssm-agent/files/patch-agent_session_shell_shell__unix.go b/sysutils/amazon-ssm-agent/files/patch-agent_session_shell_shell__unix.go
deleted file mode 100644
index 7ef13858cc9f..000000000000
--- a/sysutils/amazon-ssm-agent/files/patch-agent_session_shell_shell__unix.go
+++ /dev/null
@@ -1,11 +0,0 @@
---- agent/session/shell/shell_unix.go.orig	2023-04-01 00:01:35 UTC
-+++ agent/session/shell/shell_unix.go
-@@ -34,7 +34,7 @@ import (
- 	"github.com/aws/amazon-ssm-agent/agent/log"
- 	mgsContracts "github.com/aws/amazon-ssm-agent/agent/session/contracts"
- 	"github.com/aws/amazon-ssm-agent/agent/session/utility"
--	"github.com/kr/pty"
-+	"github.com/creack/pty"
- )
- 
- var ptyFile *os.File