diff --git a/.changelog/21277.txt b/.changelog/21277.txt
new file mode 100644
index 0000000000..a14a5aab20
--- /dev/null
+++ b/.changelog/21277.txt
@@ -0,0 +1,3 @@
+```release-note:enhancement
+mesh: update supported envoy version 1.29.5 in addition to 1.28.4, 1.27.6.
+```
\ No newline at end of file
diff --git a/.github/workflows/nightly-test-integ-peering_commontopo.yml b/.github/workflows/nightly-test-integ-peering_commontopo.yml
index 3d407a7c3c..84b8a97c1c 100644
--- a/.github/workflows/nightly-test-integ-peering_commontopo.yml
+++ b/.github/workflows/nightly-test-integ-peering_commontopo.yml
@@ -62,7 +62,7 @@ jobs:
     name: '${{matrix.test-case}}'
 
     env:
-      ENVOY_VERSION: "1.29.4"
+      ENVOY_VERSION: "1.29.5"
     steps:
       - uses: actions/checkout@0ad4b8fadaa221de15dcec353f45205ec38ea70b # v4.1.4
       # NOTE: This step is specifically needed for ENT. It allows us to access the required private HashiCorp repos.
diff --git a/.github/workflows/nightly-test-integrations-1.15.x.yml b/.github/workflows/nightly-test-integrations-1.15.x.yml
index db72e7814c..db6607bda5 100644
--- a/.github/workflows/nightly-test-integrations-1.15.x.yml
+++ b/.github/workflows/nightly-test-integrations-1.15.x.yml
@@ -117,7 +117,7 @@ jobs:
     strategy:
       fail-fast: false
       matrix:
-        envoy-version: ["1.22.11", "1.23.12", "1.24.12", "1.25.11", "1.26.8", "1.27.5", "1.28.3"]
+        envoy-version: ["1.22.11", "1.23.12", "1.24.12", "1.25.11", "1.26.8", "1.27.6", "1.28.4"]
         xds-target: ["server", "client"]
         test-cases: ${{ fromJSON(needs.generate-envoy-job-matrices.outputs.envoy-matrix) }}
     env:
diff --git a/.github/workflows/nightly-test-integrations-1.17.x.yml b/.github/workflows/nightly-test-integrations-1.17.x.yml
index dfc15a78b7..c848c7f8fe 100644
--- a/.github/workflows/nightly-test-integrations-1.17.x.yml
+++ b/.github/workflows/nightly-test-integrations-1.17.x.yml
@@ -117,7 +117,7 @@ jobs:
     strategy:
       fail-fast: false
       matrix:
-        envoy-version: ["1.24.12", "1.25.11", "1.26.8", "1.27.5"]
+        envoy-version: ["1.24.12", "1.25.11", "1.26.8", "1.27.6"]
         xds-target: ["server", "client"]
         test-cases: ${{ fromJSON(needs.generate-envoy-job-matrices.outputs.envoy-matrix) }}
     env:
diff --git a/.github/workflows/nightly-test-integrations-1.18.x.yml b/.github/workflows/nightly-test-integrations-1.18.x.yml
index 9d6ec0d5fd..ee39c4f499 100644
--- a/.github/workflows/nightly-test-integrations-1.18.x.yml
+++ b/.github/workflows/nightly-test-integrations-1.18.x.yml
@@ -74,7 +74,7 @@ jobs:
           # this is further going to multiplied in envoy-integration tests by the 
           # other dimensions in the matrix.  Currently TOTAL_RUNNERS would be
           # multiplied by 8 based on these values:
-          # envoy-version: ["1.24.12", "1.25.11", "1.26.8", "1.27.5"]
+          # envoy-version: ["1.24.12", "1.25.11", "1.26.8", "1.27.6"]
           # xds-target: ["server", "client"]
           TOTAL_RUNNERS: 4 
           JQ_SLICER: '[ inputs ] | [_nwise(length / $runnercount | floor)]'
@@ -109,7 +109,7 @@ jobs:
     strategy:
       fail-fast: false
       matrix:
-        envoy-version: ["1.24.12", "1.25.11", "1.26.8", "1.27.5"]
+        envoy-version: ["1.24.12", "1.25.11", "1.26.8", "1.27.6"]
         xds-target: ["server", "client"]
         test-cases: ${{ fromJSON(needs.generate-envoy-job-matrices.outputs.envoy-matrix) }}
     env:
diff --git a/.github/workflows/nightly-test-integrations-1.19.x.yml b/.github/workflows/nightly-test-integrations-1.19.x.yml
index 7acb1903a9..876539046f 100644
--- a/.github/workflows/nightly-test-integrations-1.19.x.yml
+++ b/.github/workflows/nightly-test-integrations-1.19.x.yml
@@ -74,7 +74,7 @@ jobs:
           # this is further going to multiplied in envoy-integration tests by the 
           # other dimensions in the matrix.  Currently TOTAL_RUNNERS would be
           # multiplied by 8 based on these values:
-          # envoy-version: ["1.24.12", "1.25.11", "1.26.8", "1.27.5"]
+          # envoy-version: ["1.24.12", "1.25.11", "1.26.8", "1.27.6"]
           # xds-target: ["server", "client"]
           TOTAL_RUNNERS: 4 
           JQ_SLICER: '[ inputs ] | [_nwise(length / $runnercount | floor)]'
@@ -109,7 +109,7 @@ jobs:
     strategy:
       fail-fast: false
       matrix:
-        envoy-version: ["1.24.12", "1.25.11", "1.26.8", "1.27.5"]
+        envoy-version: ["1.26.8", "1.27.6", "1.28.5", "1.29.5"]
         xds-target: ["server", "client"]
         test-cases: ${{ fromJSON(needs.generate-envoy-job-matrices.outputs.envoy-matrix) }}
     env:
diff --git a/.github/workflows/nightly-test-integrations.yml b/.github/workflows/nightly-test-integrations.yml
index 8634f7613a..bf914f8893 100644
--- a/.github/workflows/nightly-test-integrations.yml
+++ b/.github/workflows/nightly-test-integrations.yml
@@ -106,7 +106,7 @@ jobs:
     strategy:
       fail-fast: false
       matrix:
-        envoy-version: ["1.26.8", "1.27.5", "1.28.3", "1.29.4"]
+        envoy-version: ["1.26.8", "1.27.6", "1.28.4", "1.29.5"]
         xds-target: ["server", "client"]
         test-cases: ${{ fromJSON(needs.generate-envoy-job-matrices.outputs.envoy-matrix) }}
     env:
diff --git a/.github/workflows/test-integrations.yml b/.github/workflows/test-integrations.yml
index 20f169d6f4..cae4e9f591 100644
--- a/.github/workflows/test-integrations.yml
+++ b/.github/workflows/test-integrations.yml
@@ -272,7 +272,7 @@ jobs:
           # this is further going to multiplied in envoy-integration tests by the
           # other dimensions in the matrix.  Currently TOTAL_RUNNERS would be
           # multiplied by 2 based on these values:
-          # envoy-version: ["1.29.4"]
+          # envoy-version: ["1.29.5"]
           # xds-target: ["server", "client"]
           TOTAL_RUNNERS: 2
           JQ_SLICER: '[ inputs ] | [_nwise(length / $runnercount | floor)]'
@@ -307,7 +307,7 @@ jobs:
     strategy:
       fail-fast: false
       matrix:
-        envoy-version: ["1.29.4"]
+        envoy-version: ["1.29.5"]
         xds-target: ["server", "client"]
         test-cases: ${{ fromJSON(needs.generate-envoy-job-matrices.outputs.envoy-matrix) }}
     env:
@@ -397,7 +397,7 @@ jobs:
       id-token: write # NOTE: this permission is explicitly required for Vault auth.
       contents: read
     env:
-      ENVOY_VERSION: "1.29.4"
+      ENVOY_VERSION: "1.29.5"
       CONSUL_DATAPLANE_IMAGE: "docker.io/hashicorppreview/consul-dataplane:1.3-dev-ubi"
     steps:
       - uses: actions/checkout@0ad4b8fadaa221de15dcec353f45205ec38ea70b # v4.1.4
diff --git a/Makefile b/Makefile
index 1e643d9e4a..b4bf3807b9 100644
--- a/Makefile
+++ b/Makefile
@@ -71,7 +71,7 @@ CONSUL_IMAGE_VERSION?=latest
 # When changing the method of Go version detection, also update
 # version detection in CI workflows (reusable-get-go-version.yml).
 GOLANG_VERSION?=$(shell head -n 1 .go-version)
-ENVOY_VERSION?='1.29.4'
+ENVOY_VERSION?='1.29.5'
 CONSUL_DATAPLANE_IMAGE := $(or $(CONSUL_DATAPLANE_IMAGE),"docker.io/hashicorppreview/consul-dataplane:1.3-dev-ubi")
 DEPLOYER_CONSUL_DATAPLANE_IMAGE := $(or $(DEPLOYER_CONSUL_DATAPLANE_IMAGE), "docker.io/hashicorppreview/consul-dataplane:1.3-dev")
 
diff --git a/envoyextensions/xdscommon/envoy_versioning_test.go b/envoyextensions/xdscommon/envoy_versioning_test.go
index ab3290e576..cca8f88f78 100644
--- a/envoyextensions/xdscommon/envoy_versioning_test.go
+++ b/envoyextensions/xdscommon/envoy_versioning_test.go
@@ -152,9 +152,9 @@ func TestDetermineSupportedProxyFeaturesFromString(t *testing.T) {
 	*/
 	for _, v := range []string{
 		"1.26.0", "1.26.1", "1.26.2", "1.26.3", "1.26.4", "1.26.5", "1.26.6", "1.26.7", "1.26.8",
-		"1.27.0", "1.27.1", "1.27.2", "1.27.3", "1.27.4", "1.27.5",
-		"1.28.0", "1.28.1", "1.28.2", "1.28.3",
-		"1.29.0", "1.29.1", "1.29.2", "1.29.3", "1.29.4",
+		"1.27.0", "1.27.1", "1.27.2", "1.27.3", "1.27.4", "1.27.5", "1.27.6",
+		"1.28.0", "1.28.1", "1.28.2", "1.28.3", "1.28.4",
+		"1.29.0", "1.29.1", "1.29.2", "1.29.3", "1.29.4", "1.29.5",
 	} {
 		cases[v] = testcase{expect: SupportedProxyFeatures{}}
 	}
diff --git a/envoyextensions/xdscommon/proxysupport.go b/envoyextensions/xdscommon/proxysupport.go
index 1f71770305..77c1da0ad5 100644
--- a/envoyextensions/xdscommon/proxysupport.go
+++ b/envoyextensions/xdscommon/proxysupport.go
@@ -12,9 +12,9 @@ import "strings"
 //
 // see: https://www.consul.io/docs/connect/proxies/envoy#supported-versions
 var EnvoyVersions = []string{
-	"1.29.4",
-	"1.28.3",
-	"1.27.5",
+	"1.29.5",
+	"1.28.4",
+	"1.27.6",
 	"1.26.8",
 }
 
diff --git a/test/integration/connect/envoy/run-tests.sh b/test/integration/connect/envoy/run-tests.sh
index 0f0365215a..1f825268b0 100755
--- a/test/integration/connect/envoy/run-tests.sh
+++ b/test/integration/connect/envoy/run-tests.sh
@@ -15,7 +15,7 @@ DEBUG=${DEBUG:-}
 XDS_TARGET=${XDS_TARGET:-server}
 
 # ENVOY_VERSION to run each test against
-ENVOY_VERSION=${ENVOY_VERSION:-"1.29.4"}
+ENVOY_VERSION=${ENVOY_VERSION:-"1.29.5"}
 export ENVOY_VERSION
 
 export DOCKER_BUILDKIT=1