diff --git a/.github/renovate.json b/.github/renovate.json
index 2d0340dc9..6dd680fd7 100644
--- a/.github/renovate.json
+++ b/.github/renovate.json
@@ -477,6 +477,26 @@
         "dockerfile"
       ]
     },
+    {
+      "description": "Keep the Dockerfile's golang builder image in lockstep with go.mod/GO_VERSION bumps — prevents the Docker build failing when go.mod requires a newer Go than the pinned builder image (overrides the broader Dockerfile ARG grouping above since it matches later)",
+      "matchManagers": [
+        "custom.regex"
+      ],
+      "matchFileNames": [
+        "Dockerfile"
+      ],
+      "matchDepNames": [
+        "golang"
+      ],
+      "matchUpdateTypes": [
+        "minor",
+        "patch",
+        "pin",
+        "digest"
+      ],
+      "groupName": "go-non-major",
+      "groupSlug": "go-non-major"
+    },
     {
       "description": "Development branch: Auto-merge non-major updates after proven stable",
       "matchBaseBranches": [
diff --git a/.github/skills/examples/gorm-scanner-ci-workflow.yml b/.github/skills/examples/gorm-scanner-ci-workflow.yml
index 49b9f88b1..b0ae9bc90 100644
--- a/.github/skills/examples/gorm-scanner-ci-workflow.yml
+++ b/.github/skills/examples/gorm-scanner-ci-workflow.yml
@@ -25,7 +25,7 @@ jobs:
       - name: Setup Go
         uses: actions/setup-go@924ae3a1cded613372ab5595356fb5720e22ba16 # v6
         with:
-          go-version: "1.26.4"
+          go-version: "1.26.5"
 
       - name: Run GORM Security Scanner
         id: gorm-scan
diff --git a/.github/workflows/benchmark.yml b/.github/workflows/benchmark.yml
index be332d981..ee265e80f 100644
--- a/.github/workflows/benchmark.yml
+++ b/.github/workflows/benchmark.yml
@@ -12,7 +12,7 @@ concurrency:
   cancel-in-progress: true
 
 env:
-  GO_VERSION: '1.26.4'
+  GO_VERSION: '1.26.5'
   GOTOOLCHAIN: local
 
 # Minimal permissions at workflow level; write permissions granted at job level for push only
diff --git a/.github/workflows/codecov-upload.yml b/.github/workflows/codecov-upload.yml
index 8cdf824fb..0a665c813 100644
--- a/.github/workflows/codecov-upload.yml
+++ b/.github/workflows/codecov-upload.yml
@@ -23,7 +23,7 @@ concurrency:
   cancel-in-progress: true
 
 env:
-  GO_VERSION: '1.26.4'
+  GO_VERSION: '1.26.5'
   NODE_VERSION: '24.18.0'
   GOTOOLCHAIN: local
 
diff --git a/.github/workflows/codeql.yml b/.github/workflows/codeql.yml
index da0e93d3a..2bd995590 100644
--- a/.github/workflows/codeql.yml
+++ b/.github/workflows/codeql.yml
@@ -15,7 +15,7 @@ concurrency:
 
 env:
   GOTOOLCHAIN: local
-  GO_VERSION: '1.26.4'
+  GO_VERSION: '1.26.5'
 
 permissions:
   contents: read
diff --git a/.github/workflows/e2e-tests-split.yml b/.github/workflows/e2e-tests-split.yml
index e38a3a092..0fdf7be8b 100644
--- a/.github/workflows/e2e-tests-split.yml
+++ b/.github/workflows/e2e-tests-split.yml
@@ -83,7 +83,7 @@ on:
 
 env:
   NODE_VERSION: '24.18.0'
-  GO_VERSION: '1.26.4'
+  GO_VERSION: '1.26.5'
   GOTOOLCHAIN: local
   DOCKERHUB_REGISTRY: docker.io
   IMAGE_NAME: ${{ github.repository_owner }}/charon
diff --git a/.github/workflows/nightly-build.yml b/.github/workflows/nightly-build.yml
index 8347aa7ed..fb8d8b5dc 100644
--- a/.github/workflows/nightly-build.yml
+++ b/.github/workflows/nightly-build.yml
@@ -15,7 +15,7 @@ on:
       default: "false"
 
 env:
-  GO_VERSION: '1.26.4'
+  GO_VERSION: '1.26.5'
   NODE_VERSION: '24.18.0'
   GOTOOLCHAIN: local
   GHCR_REGISTRY: ghcr.io
diff --git a/.github/workflows/orthrus-build.yml b/.github/workflows/orthrus-build.yml
index 55b6c4581..4e45c8574 100644
--- a/.github/workflows/orthrus-build.yml
+++ b/.github/workflows/orthrus-build.yml
@@ -29,7 +29,7 @@ env:
   GHCR_REGISTRY: ghcr.io
   DOCKERHUB_REGISTRY: docker.io
   IMAGE_NAME: wikid82/orthrus
-  GO_VERSION: '1.26.4'
+  GO_VERSION: '1.26.5'
 
 permissions:
   contents: read
diff --git a/.github/workflows/quality-checks.yml b/.github/workflows/quality-checks.yml
index 0a23f2da3..22e0b7e91 100644
--- a/.github/workflows/quality-checks.yml
+++ b/.github/workflows/quality-checks.yml
@@ -16,7 +16,7 @@ permissions:
   checks: write
 
 env:
-  GO_VERSION: '1.26.4'
+  GO_VERSION: '1.26.5'
   NODE_VERSION: '24.18.0'
   GOTOOLCHAIN: local
 
diff --git a/.github/workflows/release-goreleaser.yml b/.github/workflows/release-goreleaser.yml
index 516cba748..bad8ca777 100644
--- a/.github/workflows/release-goreleaser.yml
+++ b/.github/workflows/release-goreleaser.yml
@@ -10,7 +10,7 @@ concurrency:
   cancel-in-progress: false
 
 env:
-  GO_VERSION: '1.26.4'
+  GO_VERSION: '1.26.5'
   NODE_VERSION: '24.18.0'
   GOTOOLCHAIN: local
 
diff --git a/.github/workflows/renovate.yml b/.github/workflows/renovate.yml
index e514d79aa..cbf7b4c7d 100644
--- a/.github/workflows/renovate.yml
+++ b/.github/workflows/renovate.yml
@@ -11,7 +11,12 @@ concurrency:
 
 # Renovate authenticates via the RENOVATE_TOKEN PAT; GITHUB_TOKEN is only used by checkout.
 permissions:
-  contents: read
+  contents: write
+  pull-requests: write
+  issues: write
+
+env:
+  GO_VERSION: '1.26.5'
 
 jobs:
   renovate:
diff --git a/.grype.yaml b/.grype.yaml
index 64fc1fdff..376f7653b 100644
--- a/.grype.yaml
+++ b/.grype.yaml
@@ -840,6 +840,61 @@ ignore:
 
     # Action items: same as GO-2026-5024 entry above.
 
+  # GO-2026-5932: golang.org/x/crypto/openpgp is unmaintained, unsafe by design
+  # Severity: UNKNOWN in Go vulndb (Trivy substitutes another vendor's rating) —
+  # Package: golang.org/x/crypto v0.53.0, flagged in /app/charon, /usr/bin/caddy,
+  # /usr/local/bin/crowdsec, /usr/local/bin/cscli
+  #
+  # Vulnerability Details:
+  # - Go's advisory database flags golang.org/x/crypto/openpgp as unmaintained and unsafe by
+  #   design (not a specific exploitable bug) and recommends migrating to a maintained fork
+  #   such as github.com/ProtonMail/go-crypto.
+  # - No fixed version is recorded — this cannot be resolved by upgrading golang.org/x/crypto.
+  #
+  # Root Cause of Suppression (No Fix Path):
+  # - Trivy's gobinary scanner flags based on module versions embedded in the compiled binary's
+  #   buildinfo, not on which subpackages are actually imported/linked.
+  # - Verified via `go list -deps ./...` in backend: the openpgp subpackage is not imported
+  #   anywhere in Charon's own code. app/charon is a false positive.
+  # - caddy, crowdsec, and cscli are third-party binaries built in the Dockerfile; x/crypto is
+  #   a transitive dependency of theirs that we don't control the internals of.
+  #
+  # Risk Assessment: ACCEPTED (no fix exists; not reachable via Charon's own code)
+  # - Charon's own binary does not call any x/crypto/openpgp API.
+  # - No upstream action can resolve this short of the vendor projects dropping the dependency.
+  #
+  # Mitigation:
+  # - Monitor whether caddy/crowdsec/cscli upstream drop their dependency on x/crypto/openpgp.
+  # - Re-run govulncheck periodically to confirm Charon's own code stays clean.
+  #
+  # Review:
+  # - Initial suppression 2026-07-08: no fixed version exists; false positive for app/charon.
+  # - Next review: 2026-08-08.
+  #
+  # Removal Criteria:
+  # - Go vulndb publishes a fixed version for golang.org/x/crypto, OR
+  # - Trivy adds subpackage-aware (symbol-level) matching instead of module-level matching
+  #
+  # References:
+  # - GO-2026-5932: https://pkg.go.dev/vuln/GO-2026-5932
+  - vulnerability: GO-2026-5932
+    package:
+      name: golang.org/x/crypto
+      version: "v0.53.0"
+      type: go-module
+    reason: |
+      UNKNOWN/HIGH — golang.org/x/crypto/openpgp is flagged as unmaintained and unsafe by design.
+      No fixed version exists; this is not a patchable bug. Verified via `go list -deps ./...`
+      that Charon's own code (app/charon) does not import the openpgp subpackage — false positive
+      from Trivy's module-level (not symbol-level) binary scanning. caddy/crowdsec/cscli are
+      third-party binaries with their own transitive dependency on x/crypto.
+    expiry: "2026-08-08"  # Review: Initial suppression 2026-07-08. Next review: 2026-08-08.
+
+    # Action items when this suppression expires:
+    # 1. Check if Go vulndb has published a fixed version for golang.org/x/crypto
+    # 2. Re-run `go list -deps ./...` in backend to confirm openpgp is still not imported
+    # 3. If neither changes: extend expiry by 30 days
+
 # Match exclusions (patterns to ignore during scanning)
 # Use sparingly - prefer specific CVE suppressions above
 match:
diff --git a/.trivyignore b/.trivyignore
index 9109c8bed..e272e5d63 100644
--- a/.trivyignore
+++ b/.trivyignore
@@ -163,3 +163,18 @@ CVE-2024-21492
 # See also: .grype.yaml for full justification
 # exp: 2026-09-23
 CVE-2026-39824
+
+# GO-2026-5932: golang.org/x/crypto/openpgp is unmaintained, unsafe by design
+# Severity: reported UNKNOWN by Go vulndb; Trivy falls back to another vendor's severity rating
+# Package: golang.org/x/crypto v0.53.0 — flagged in /app/charon, /usr/bin/caddy,
+# /usr/local/bin/crowdsec, /usr/local/bin/cscli
+# No fixed version exists: this advisory does not describe a patchable bug, it is Go's standing
+# recommendation to stop using the openpgp subpackage entirely (superseded by
+# github.com/ProtonMail/go-crypto). No golang.org/x/crypto version resolves this.
+# Verified `go list -deps ./...` in backend: the openpgp subpackage is not imported anywhere in
+# Charon's own code — app/charon is flagged purely because Trivy's gobinary scan checks module
+# versions embedded in the binary, not which subpackages are actually linked in.
+# caddy/crowdsec/cscli are third-party binaries; x/crypto is a transitive dependency we don't control.
+# Review by: 2026-08-08
+# exp: 2026-08-08
+GO-2026-5932
diff --git a/.vscode/tasks.json b/.vscode/tasks.json
index 9c43fbcef..43883284d 100644
--- a/.vscode/tasks.json
+++ b/.vscode/tasks.json
@@ -1062,7 +1062,7 @@
         {
             "label": "Utility: Update Go Version",
             "type": "shell",
-            "command": "go env -w GOTOOLCHAIN=go$(go list -m -f '{{.Version}}' go@latest)+auto && go list -m -f '{{.Version}}' go@latest && go version",
+            "command": "./scripts/update-go-toolchain.sh",
             "group": "none",
             "problemMatcher": [],
             "presentation": {
diff --git a/Dockerfile b/Dockerfile
index 14b748c03..30635c44a 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -10,7 +10,7 @@ ARG BUILD_DEBUG=0
 
 # ---- Pinned Toolchain Versions ----
 # renovate: datasource=docker depName=golang versioning=docker
-ARG GO_VERSION=1.26.4
+ARG GO_VERSION=1.26.5
 
 # renovate: datasource=docker depName=alpine versioning=docker
 ARG ALPINE_IMAGE=alpine:3.24.1@sha256:28bd5fe8b56d1bd048e5babf5b10710ebe0bae67db86916198a6eec434943f8b
diff --git a/SECURITY.md b/SECURITY.md
index 9059c435c..432eccc64 100644
--- a/SECURITY.md
+++ b/SECURITY.md
@@ -368,6 +368,53 @@ decode path. Charon defaults to SQLite, so standard deployments do not expose th
 Track upstream CrowdSec dependency updates and remove suppression once pgx/v4 is no longer
 present in bundled components.
 
+---
+
+### [HIGH] GO-2026-5932 · golang.org/x/crypto/openpgp Unmaintained, Unsafe by Design
+
+| Field        | Value |
+|--------------|-------|
+| **ID**       | GO-2026-5932 |
+| **Severity** | Reported Unknown by Go vulndb; Trivy substitutes another vendor's rating |
+| **Status**   | Awaiting Upstream (no fixed version exists) |
+
+**What**
+`golang.org/x/crypto/openpgp` v0.53.0 is flagged by the Go vulnerability database as
+unmaintained and unsafe by design — this is not a specific patchable bug, it is Go's standing
+recommendation to migrate off the openpgp subpackage entirely (superseded by
+`github.com/ProtonMail/go-crypto`). No fixed `golang.org/x/crypto` version resolves this.
+
+**Who**
+
+- Discovered by: Automated scan (Trivy image scan, PR #1133)
+- Reported: 2026-07-08
+- Affects: `app/charon`, `usr/bin/caddy`, `usr/local/bin/crowdsec`, `usr/local/bin/cscli`
+
+**Where**
+
+- Component: `golang.org/x/crypto` v0.53.0 (declared dependency; embedded across all four binaries)
+- Versions affected: all versions containing the `openpgp` subpackage — no fix exists
+
+**When**
+
+- Discovered: 2026-07-08
+- Disclosed (if public): Public
+- Target fix: N/A — no fixed version will be published; suppression is permanent absent a
+  Trivy scanner change to symbol-level (rather than module-level) matching
+
+**How**
+Trivy's `gobinary` scanner flags based on module versions recorded in the binary's embedded
+build info, not on which subpackages are actually imported and linked. Verified via
+`go list -deps ./...` in `backend`: the `openpgp` subpackage is not imported anywhere in
+Charon's own code, so the `app/charon` finding is a false positive. `caddy`, `crowdsec`, and
+`cscli` are third-party binaries built in the Dockerfile; `golang.org/x/crypto` is a transitive
+dependency of theirs that Charon does not control.
+
+**Planned Remediation**
+No remediation path exists upstream. Monitor whether caddy/crowdsec/cscli drop their dependency
+on `x/crypto/openpgp`, and periodically re-run `govulncheck` to confirm Charon's own code stays
+clean. Suppressed in `.trivyignore` and `.grype.yaml`; review 2026-08-08.
+
 ## Patched Vulnerabilities
 
 ### ✅ [HIGH] CVE-2026-34040 · Docker AuthZ Plugin Bypass via Oversized Request Body
diff --git a/agent/go.mod b/agent/go.mod
index 1f0912053..3e40b329a 100644
--- a/agent/go.mod
+++ b/agent/go.mod
@@ -1,6 +1,6 @@
 module github.com/Wikid82/charon/agent
 
-go 1.26.4
+go 1.26.5
 
 require (
 	github.com/gorilla/websocket v1.5.3
diff --git a/backend/go.mod b/backend/go.mod
index 1714d39e5..0b4048731 100644
--- a/backend/go.mod
+++ b/backend/go.mod
@@ -1,6 +1,6 @@
 module github.com/Wikid82/charon/backend
 
-go 1.26.4
+go 1.26.5
 
 require (
 	github.com/gin-contrib/gzip v1.2.6
diff --git a/go.work b/go.work
index 7a85b66f5..fe3169ac3 100644
--- a/go.work
+++ b/go.work
@@ -1,4 +1,4 @@
-go 1.26.4
+go 1.26.5
 
 use (
 	./agent
diff --git a/scripts/update-go-toolchain.sh b/scripts/update-go-toolchain.sh
new file mode 100755
index 000000000..ff8f3676d
--- /dev/null
+++ b/scripts/update-go-toolchain.sh
@@ -0,0 +1,41 @@
+#!/usr/bin/env bash
+# Pin GOTOOLCHAIN to the latest Go release, prune stale cached toolchains,
+# and kick gopls so it picks up the new version without a manual editor reload.
+#
+# gopls is a long-running process: it resolves its Go toolchain once at
+# startup and never re-reads GOTOOLCHAIN afterwards. Without a restart here,
+# the editor keeps reporting "go.work requires go >= X (running go Y)" even
+# though `go version` in a fresh shell is already correct.
+
+set -euo pipefail
+
+LATEST_VERSION="$(go list -m -f '{{.Version}}' go@latest)"
+echo "Latest Go release: go${LATEST_VERSION}"
+
+go env -w "GOTOOLCHAIN=go${LATEST_VERSION}+auto"
+echo "GOTOOLCHAIN pinned to go${LATEST_VERSION}+auto"
+
+TOOLCHAIN_CACHE="$(go env GOMODCACHE)/golang.org"
+if [ -d "$TOOLCHAIN_CACHE" ]; then
+    echo "Pruning cached toolchains older than go${LATEST_VERSION}..."
+    for dir in "$TOOLCHAIN_CACHE"/toolchain@v*; do
+        [ -e "$dir" ] || continue
+        case "$dir" in
+            *"go${LATEST_VERSION}."*) continue ;;
+        esac
+        chmod -R u+w "$dir"
+        rm -rf "$dir"
+        echo "  removed $(basename "$dir")"
+    done
+fi
+
+if pkill -x gopls 2>/dev/null; then
+    echo "Restarted gopls (killed stale process; your editor will respawn it)."
+else
+    echo "No running gopls process found to restart."
+fi
+
+echo ""
+go version
+echo ""
+echo "Done. If your editor still shows a stale Go version, run 'Developer: Reload Window'."