diff --git a/docs/CHATWOOT_PARITY_DEVELOPMENT_PLAN.md b/docs/CHATWOOT_PARITY_DEVELOPMENT_PLAN.md
index 0bce6d74..77008fc1 100644
--- a/docs/CHATWOOT_PARITY_DEVELOPMENT_PLAN.md
+++ b/docs/CHATWOOT_PARITY_DEVELOPMENT_PLAN.md
@@ -16,10 +16,10 @@ Build GoChat as a Go backend that can directly reuse the frontend from `referenc
 
 ## Current Baseline
 
-- Current tracking checkpoint: 2026-06-06 after `2ab7b58 feat(accounts): align account payloads`, with this documentation checkpoint prepared as `docs: refresh parity tracker baseline`.
-- Latest implementation checkpoint: `2ab7b58 feat(accounts): align account payloads`.
-- Latest documentation-only checkpoint: this checkpoint, prepared as `docs: refresh parity tracker baseline`; this document is now the active follow-up plan and supersedes `.hermes/plans/*`.
-- Worktree status at this documentation checkpoint: clean after `2ab7b58`. B11.1a aligns Captain assistant CRUD/tools/inbox bindings; B11.1b aligns Captain scenarios and custom tools; B11.1c aligns Captain documents, assistant responses, bulk actions, and custom-tool test payloads; B11.2 aligns Copilot thread/message create/list/get/delete payloads, account/user scoping, and no-LLM fallback persistence; B11.3a aligns Captain preferences show/update payloads and account-level model/feature storage; B11.3b aligns Captain playground request/response payloads, account scoping, and no-LLM fallback; B11.3c adds the fakeable Captain document sync backend gate with disabled, failed, and fake-success states; B11.3d aligns Captain task request/response payloads, no-provider disabled states, follow-up context, suggestion persistence, and Copilot message tool-call key validation; B11.3e aligns Captain stream DTOs/disabled SSE fallbacks and Copilot push-event payload shapes; B12.1 adds the reusable GoChat server/seed entrypoint plus a Meilisearch-first reused Chatwoot frontend smoke harness and report; B12.2a adds API smoke assertions for auth/profile, inbox, conversation/messages, contact/company, widget config/message, and public CSAT; B12.2b adds a zero-dependency Chrome DevTools browser smoke that loads the reused Chatwoot login and dashboard entrypoints through Vite and checks browser auth/dashboard API requests; B12.3a adds enterprise API smoke assertions for SLA reports/download, CSAT reports/download, automation/macros, audit/custom roles, capacity, Captain, and Copilot; B12.3b adds reused-frontend enterprise browser route navigation for SLA, CSAT, automation, macros, audit logs, custom roles, capacity, Captain, and Copilot request coverage; P5 durable job work through P5.13b is in Review; B9.3 verifies the current reference exposes no delayed automation action params and completes remaining automation action side effects; Phase 2/3 drift now aligns notifications, auth reset/confirmation, CRM shared attachments, account payloads, agents, teams, team members, and assignable-agent payload envelopes. Next active implementation slice is P3.6 label CRUD payload parity, followed by continued Phase 6 placeholder audit from fresh reference/smoke evidence.
+- Current tracking checkpoint: 2026-06-06 after `8b378c7 docs: refresh parity tracker baseline`, with this implementation checkpoint prepared as `feat(labels): align chatwoot label payloads`.
+- Latest implementation checkpoint: this checkpoint, prepared as `feat(labels): align chatwoot label payloads`.
+- Latest documentation-only checkpoint: `8b378c7 docs: refresh parity tracker baseline`; this document is now the active follow-up plan and supersedes `.hermes/plans/*`.
+- Worktree status at this implementation checkpoint: P3.6 label CRUD now aligns Chatwoot account `/labels` list/create/show/update/delete payloads, `title/description/color/show_on_sidebar` persistence, nested frontend request bodies, legacy `/tags` compatibility, account-scoped lookup, empty `200 OK` delete, and label association cleanup/rename side effects. B11.1a aligns Captain assistant CRUD/tools/inbox bindings; B11.1b aligns Captain scenarios and custom tools; B11.1c aligns Captain documents, assistant responses, bulk actions, and custom-tool test payloads; B11.2 aligns Copilot thread/message create/list/get/delete payloads, account/user scoping, and no-LLM fallback persistence; B11.3a aligns Captain preferences show/update payloads and account-level model/feature storage; B11.3b aligns Captain playground request/response payloads, account scoping, and no-LLM fallback; B11.3c adds the fakeable Captain document sync backend gate with disabled, failed, and fake-success states; B11.3d aligns Captain task request/response payloads, no-provider disabled states, follow-up context, suggestion persistence, and Copilot message tool-call key validation; B11.3e aligns Captain stream DTOs/disabled SSE fallbacks and Copilot push-event payload shapes; B12.1/B12.2/B12.3 smoke harnesses remain in Review; P5 durable job work through P5.13b is in Review. Next active implementation slice is continued Phase 6 placeholder audit from fresh reference/smoke evidence, then the next P3.6 custom-attributes/custom-filters drift slice.
 - `go test ./...` passes.
 - Route dump succeeds with `TOTAL: 837` after adding Chatwoot auth reset/confirmation routes and `GET /api/v1/accounts/:account_id/contacts/:contact_id/attachments`.
 - Route parity artifacts now exist under `docs/parity/` and are generated by `cmd/route_parity`.
@@ -87,7 +87,7 @@ This table is the shortest authoritative handoff view. If an older lower section
 
 | Priority | Workstream | Current state | Next checkpoint | Commit close rule |
 | --- | --- | --- | --- | --- |
-| 1 | Phase 2/3 drift | Tracked route parity is 0 missing for the current critical set; notification list/action serializers, Devise password reset/confirmation payloads, CRM shared attachment payloads, account show/update/create/cache-key/active-at payloads, settings agents/teams payloads, and assignable-agent payloads now match Chatwoot's frontend contract. Label CRUD drift is now captured as P3.6. | Land P3.6 label CRUD payload parity, then expand route/serializer fixtures when smoke or reference inspection exposes more drift. | Regenerate parity artifacts when routes change and add endpoint-family fixture tests. |
+| 1 | Phase 2/3 drift | Tracked route parity is 0 missing for the current critical set; notification list/action serializers, Devise password reset/confirmation payloads, CRM shared attachment payloads, account/settings payloads, assignable-agent payloads, and label CRUD payloads now match Chatwoot's frontend contract. | Continue Phase 6 placeholder audit, then open the next P3.6 custom-attributes/custom-filters drift slice from reference/smoke evidence. | Regenerate parity artifacts when routes change and add endpoint-family fixture tests. |
 | 2 | Phase 6 placeholder audit | Widget/public/webhook critical placeholders are burned down; inbox WhatsApp health/register-webhook and sync-template drift are closed; account/contact/conversation/message/inbox audit remains broad. | Continue fresh placeholder audit and assign every frontend-reachable stub to a tracked owner. | `rg` placeholder audit is recorded and no reused-frontend blocker is ownerless. |
 | 3 | B12 optional live smoke | API/browser/enterprise smoke commands are checked in; live runs need PostgreSQL, Redis, Meilisearch, Vite, and Chrome. | Run full live smoke when environment is available and map failures to the board. | `docs/parity/frontend_smoke_report.md` records pass/fail and linked owners. |
 | 4 | B9.3 delayed automation actions | Current reference exposes no delayed automation action params; scheduled-item work is already P5.12; `send_email_to_team` is durable and `add_sla` mutates conversation/applied SLA state. | Keep automation drift closed if future reference/smoke exposes delayed params or unsupported action shapes. | Automation worker/action fixtures verify queued team email replay, retry visibility through worker jobs, and SLA action idempotency. |
@@ -104,7 +104,7 @@ These rows are the executable development plan from this point forward. A checkp
 | P5.11c Copilot and conversation response jobs | `internal/service/copilot_service.go`, `internal/service/copilot_response_worker.go`, `internal/service/captain_conversation_service.go`, `internal/service/message_service.go`, `internal/app/bootstrap.go` | `enterprise/app/jobs/captain/copilot/response_job.rb`, `enterprise/app/jobs/captain/conversation/response_builder_job.rb`, `enterprise/app/services/captain/copilot/chat_service.rb`, `enterprise/app/services/enterprise/message_templates/hook_execution_service.rb`, `enterprise/app/models/copilot_message.rb` | Queue assistant replies after Copilot user messages and Captain pending-conversation triggers. Persist assistant messages, enqueue Captain conversation replies/handoff messages, open handoff conversations, and keep fakeable provider disabled/failure states observable through durable retry. | Review by `feat(captain): queue copilot response jobs`; focused tests cover Copilot enqueue/persist/fallback/retry, Captain conversation enqueue/handoff/retry/non-pending skip, and service/worker/app package replay. |
 | P5.13a analytics placeholder burn-down | `internal/service/analytics_service.go`, `internal/service/analytics_query_helpers.go`, live/report handlers | Chatwoot `live_reports_controller.rb`, `reports_controller.rb`, `BotMetricsBuilder`, `InboxLabelMatrixBuilder`, `FirstResponseTimeDistributionBuilder`, `OutgoingMessagesCountBuilder` | Replace frontend-visible zero/empty placeholder responses for live conversations, grouped live conversations, bot summary/metrics, conversation summary, inbox-label matrix, first-response distribution, and outgoing-message counts with persisted conversation/message/reporting-event queries. | Review by `feat(reports): derive analytics aggregates`; focused service/handler tests prove non-zero values from persisted rows and `rg` finds no placeholder TODOs in these methods. |
 | P5.13b scheduled/cached analytics | `internal/service/analytics_service.go`, `internal/service/analytics_query_helpers.go`, `internal/service/reporting_rollup_worker.go`, `internal/service/reporting_rollup_service.go`, report handlers/services, worker bootstrap | Chatwoot report controllers/services used by dashboard analytics, `Reports::DataSource`, reporting rollup/backfill jobs | Wire scheduled or lazy cached rollup freshness/idempotency and route `GET /reports` to metric timeseries instead of the summary handler. Define freshness rules for expensive rollups. | Review by `feat(reports): add analytics timeseries rollups`; report fixtures prove timeseries values are derived from persisted conversations/messages/reporting events, rollups refresh idempotently, durable `reporting:rollup_day` jobs replay, and hidden placeholder report JSON does not reappear. |
-| P3.6 label CRUD payload parity | `internal/handler/api/v1/label_handler.go`, `internal/service/tag_service.go`, `internal/model/tag.go`, `internal/repository/tag_repo.go`, migrations, label handler/service tests | `reference/chatwoot/app/controllers/api/v1/accounts/labels_controller.rb`, `app/views/api/v1/accounts/labels/*.json.jbuilder`, `app/models/label.rb`, `db/schema.rb`, dashboard `api/labels.js`, `store/modules/labels.js` | Align account `/labels` CRUD with Chatwoot: list returns `{ payload: [...] }`; create/show/update return raw `{ id, title, description, color, show_on_sidebar }`; delete returns empty `200 OK` and removes/renames associated conversation/contact labels when title changes or is destroyed. Add persisted `description` and `show_on_sidebar`, default color `#1f93ff`, title lowercasing/uniqueness, nested `{ label: ... }` bodies with legacy `name` compatibility, account-scoped lookup, and keep `/tags` aliases only as local compatibility surfaces. | Review by `feat(labels): align chatwoot label payloads`; focused handler/service/model tests cover frontend `response.data.payload` and raw mutation bodies, title/name compatibility, defaults, update/delete association side effects, and no local `{ success, data }` envelope. Run `go test ./internal/handler/api/v1 -run LabelHandler -count=1`, `go test ./internal/service -run 'TagService|LabelService' -count=1`, combined handler/service/router tests, full `go test ./...`, and `git diff --check`. |
+| P3.6 label CRUD payload parity | `internal/handler/api/v1/label_handler.go`, `internal/service/tag_service.go`, `internal/model/tag.go`, `internal/repository/tag_repo.go`, migrations, label handler/service tests | `reference/chatwoot/app/controllers/api/v1/accounts/labels_controller.rb`, `app/views/api/v1/accounts/labels/*.json.jbuilder`, `app/models/label.rb`, `db/schema.rb`, dashboard `api/labels.js`, `store/modules/labels.js` | Account `/labels` CRUD now returns Chatwoot `{ payload: [...] }` lists, raw mutation/show payloads, empty `200 OK` delete, `title/description/color/show_on_sidebar` persistence, title lowercasing/uniqueness, account scope, nested `{ label: ... }` request bodies, legacy `name` compatibility, default color, and local association cleanup/rename side effects. | Review by `feat(labels): align chatwoot label payloads`; focused handler/service/repository tests, combined handler/service/router tests, `go test ./cmd/migrate -count=1`, full `go test ./...`, and `git diff --check` passed. |
 | Phase 2/3 drift audit | `cmd/route_parity`, `docs/parity/*`, serializer tests | `reference/chatwoot/config/routes.rb`, controller Jbuilder views, reused frontend API clients | Convert any smoke/reference mismatch into a named route, controller, or serializer slice. Static route extraction remains acceptable until Ruby/Bundler is available. | Regenerated route parity shows 0 missing tracked frontend routes; new serializer fixtures cover the drift. |
 | Phase 6 placeholder burn-down | Account/contact/conversation/message/inbox handlers and services | Matching reference controllers/Jbuilder views plus reused frontend screens | Re-run placeholder audit and assign every frontend-reachable stub to a specific owner. Burn down the highest-impact stubs before broad feature expansion. | `rg` placeholder audit is recorded here; no reused-frontend critical path is ownerless. |
 | B12 live smoke | `scripts/parity_frontend_smoke.sh`, `docs/parity/frontend_smoke_report.md`, `cmd/gochat` | Reused `reference/chatwoot` Vite frontend, dashboard route/API clients | Run optional live API/browser/enterprise smoke with PostgreSQL, Redis, Meilisearch, GoChat, Vite, and Chrome. Convert failures into named rows above. | Smoke report records command, environment, pass/fail, artifacts, and linked follow-up owners. |
@@ -140,6 +140,7 @@ This ledger records the committed parity checkpoints that future slices should b
 
 | Commit | Scope | Verification summary | Follow-up state |
 | --- | --- | --- | --- |
+| `feat(labels): align chatwoot label payloads` | Advances P3.6 label CRUD parity by aligning account `/labels` with Chatwoot `LabelsController`, label Jbuilder views, `Label` model/schema, and dashboard labels API/store. List now returns `{ payload }`; create/show/update return raw label payloads with `id`, `title`, `description`, `color`, and `show_on_sidebar`; create/update accept nested `{ label }` bodies and legacy raw `name`; delete returns empty `200 OK`; title normalization, default color, account scope, persisted description/sidebar flags, and local conversation/contact association cleanup are covered. | `go test ./internal/handler/api/v1 -run LabelHandler -count=1`; `go test ./internal/service -run 'TagService|LabelService' -count=1`; `go test ./internal/repository -run TagRepo -count=1`; `go test ./internal/handler/api/v1 ./internal/service ./internal/router -count=1`; `go test ./cmd/migrate -count=1`; `go test ./...`; `git diff --check`. | P3.6 label CRUD moves to Review; continue Phase 6 placeholder audit, then custom attributes/custom filters drift. |
 | `docs: refresh parity tracker baseline` | Documentation-only checkpoint after `2ab7b58 feat(accounts): align account payloads`. Refreshes the Current Baseline to the committed account payload work, records the clean handoff state, and lands the next executable P3.6 label CRUD parity contract from direct Chatwoot reference/frontend inspection. | `git diff --check`. No Go code changed. | Start `feat(labels): align chatwoot label payloads`, then continue Phase 6 placeholder audit. |
 | `feat(accounts): align account payloads` | Advances Phase 2/3 account settings parity by aligning core reused-frontend account endpoints with Chatwoot `AccountsController`, `_account.json.jbuilder`, `show/update/create` views, dashboard `account.js`, and the account Vuex store. Account show/update/settings now return raw account objects instead of local `{ success, data }` envelopes, with `settings`, `custom_attributes`, `features`, `cache_keys`, `support_email`, `created_at`, locale/name/domain/status fields. Authenticated account creation accepts Chatwoot `account_name` and returns `{ data: { account_id } }` for the add-account modal. `update_active_at` now returns empty `200 OK`, and `cache_keys` now returns Chatwoot `{ cache_keys: { label, inbox, team } }` with zero-epoch defaults. | `go test ./internal/handler/api/v1 -run AccountHandler -count=1`; `go test ./internal/service -run AccountService -count=1`; `go test ./internal/handler/api/v1 ./internal/service ./internal/router -count=1`; `go test ./...`; `git diff --check`. | P3.2 remains Doing for account users/invitations/permissions drift; continue Phase 6 placeholder audit from fresh reference/smoke evidence. |
 | `feat(settings): align assignable agents payloads` | Advances P3.2/P3.3 settings and inbox assignment parity by aligning `GET /api/v1/accounts/:account_id/assignable_agents` and `GET /api/v1/accounts/:account_id/inboxes/:inbox_id/assignable_agents` with Chatwoot `AssignableAgentsController#index`, `inboxes#assignable_agents`, and `_agent.json.jbuilder`. Assignable-agent endpoints now return `{ payload: [...] }` instead of the local `{ success, data }` envelope and serialize agent fields required by the reused conversation assignment UI: `account_id`, `availability_status`, `auto_offline`, `confirmed`, `provider`, `available_name`, `thumbnail`, role, and enterprise `custom_role_id`. AccountUser role, availability, auto-offline, and custom-role data are loaded from the account membership instead of the global user role. | `go test ./internal/handler/api/v1 -run AssignableAgent -count=1`; `go test ./internal/service -run AssignableAgent -count=1`; `go test ./internal/handler/api/v1 ./internal/service ./internal/router -count=1`; `go test ./...`; `git diff --check`. | P3.2/P3.3 remain Doing for deeper account users/invitations/permissions and inbox serializer drift; continue Phase 6 placeholder audit from fresh reference/smoke evidence. |
@@ -260,11 +261,11 @@ This ledger records the committed parity checkpoints that future slices should b
 
 ## Next Slice Contract
 
-Completed implementation slice: `2ab7b58 feat(accounts): align account payloads` now closes the core reused-frontend account show/update/create/cache-key/active-at payload drift.
+Completed implementation slice: P3.6 label CRUD now closes the reused-frontend account label list/create/show/update/delete payload drift.
 
-Completed documentation slice: this checkpoint refreshes the tracker baseline after the latest implementation commits and adds the P3.6 label CRUD payload contract from direct `reference/chatwoot` inspection.
+Completed documentation slice: this checkpoint records the label CRUD implementation, verification commands, and next handoff target in the active tracker.
 
-Next implementation slice: land P3.6 label CRUD payload parity, then continue Phase 6 placeholder burn-down. Optional B12 live smoke remains environment-dependent and should convert failures into named slice owners.
+Next implementation slice: continue Phase 6 placeholder burn-down from a fresh audit, then open the next P3.6 custom-attributes/custom-filters drift slice from reference or smoke evidence. Optional B12 live smoke remains environment-dependent and should convert failures into named slice owners.
 
 | Step | Required result | Reference source | Verification |
 | --- | --- | --- | --- |
@@ -296,7 +297,8 @@ Next implementation slice: land P3.6 label CRUD payload parity, then continue Ph
 | N26 | Keep B12.1 smoke harness as the current frontend verification baseline. | `reference/chatwoot` frontend boot scripts and GoChat dev/test boot flow. | Done by `test(parity): add frontend smoke harness`; next step is B12.2 browser/API assertions against the checked command/report. |
 | N27 | Keep Hermes source plans mapped but inactive. | `.hermes/plans/2025-05-24-global-search-meilisearch.md`, `.hermes/plans/2026-05-24-automation-macro-csat.md`. | New work must update this tracker directly; Hermes files are read-only source notes unless the user asks otherwise. |
 | N28 | Update this tracker after every implementation checkpoint. | This document. | `git diff --check`; `go test ./...` for Go changes. |
-| N29 | Land P3.6 label CRUD payload parity before resuming broad placeholder burn-down. | Chatwoot labels controller/views/model/schema and dashboard labels API/store. | Owner row above defines code files, payloads, persistence, association side effects, and exit commands for `feat(labels): align chatwoot label payloads`. |
+| N29 | Keep P3.6 label CRUD as current label baseline. | Chatwoot labels controller/views/model/schema and dashboard labels API/store. | Done by `feat(labels): align chatwoot label payloads`; raw/list payloads, persistence, account scope, and association cleanup are covered. |
+| N30 | Resume Phase 6 placeholder burn-down from fresh evidence. | `rg` placeholder audit, reused frontend API calls, matching reference controllers/Jbuilder views. | Next implementation slice should record every frontend-reachable stub owner and burn down the highest-impact remaining placeholder. |
 
 Current B2 profile checkpoint:
 
@@ -1549,7 +1551,7 @@ Frontend-critical API groups to audit first:
 | P3.3 | Inboxes/channels | Inbox CRUD, assignable agents, avatars, channel config, business hours, widget config. | Review; assignable-agent payload drift closed, broader inbox serializer drift remains evidence-driven. |
 | P3.4 | Conversations/messages | List filters, status changes, assignment, labels, private notes, attachments, drafts, typing/read events. | Review |
 | P3.5 | Contacts/companies | CRUD, merge, labels, notes, custom attributes, import/export, conversations relation, and shared attachments. | Doing |
-| P3.6 | Labels/custom attributes/custom filters | Create/update/list behavior and exact response shapes. | Doing; label CRUD drift is captured as the next named checkpoint with Chatwoot `title/description/color/show_on_sidebar` payloads and raw/list response contracts. |
+| P3.6 | Labels/custom attributes/custom filters | Create/update/list behavior and exact response shapes. | Doing; label CRUD is in Review with Chatwoot `title/description/color/show_on_sidebar` payloads and raw/list response contracts, while custom attributes/custom filters remain evidence-driven follow-ups. |
 | P3.7 | Notifications/reports/help center/campaigns | Frontend-visible payloads and pagination/error envelopes. | Doing; notifications and reports now have focused Chatwoot payload fixtures, help center/campaigns remain broader audit scope. |
 | P3.8 | Widget/public APIs | Widget init, campaigns, config, contact, conversations, messages, direct uploads, public inbox flow, public CSAT. | Doing |
 | P3.9 | Search payloads | Global search and entity search documents backed by Meilisearch. | Review |
@@ -2059,6 +2061,7 @@ Verification milestone gates:
 
 ## Progress Log
 
+- 2026-06-06: P3.6 label CRUD checkpoint prepared as `feat(labels): align chatwoot label payloads`; audited Chatwoot `LabelsController`, label Jbuilder views, `Label` model/schema, and dashboard labels API/store. Account `/labels` list now returns `{ payload }`, create/show/update return raw label payloads, create/update accept nested `{ label }` bodies plus legacy raw `name`, title values are normalized/lowercased, color defaults to `#1f93ff`, `description` and `show_on_sidebar` are persisted, account-scoped get/update/delete prevents cross-account access, and delete returns empty `200 OK` while removing conversation/contact label associations and legacy conversation label text. Focused label handler/service/repository tests, combined handler/service/router tests, migration tests, full `go test ./...`, and `git diff --check` passed; continue Phase 6 placeholder audit next.
 - 2026-06-06: Documentation checkpoint prepared as `docs: refresh parity tracker baseline`; current baseline now points at `2ab7b58 feat(accounts): align account payloads`, the clean handoff state is recorded, and P3.6 label CRUD parity is fully landed as the next executable slice. Direct reference audit covered `LabelsController`, label Jbuilder views, `Label` model/schema, and dashboard labels API/store; current Go gaps are local `{ success, data }` envelopes, `name` instead of `title`, missing `description/show_on_sidebar/default color`, `201/204` status drift, and missing label title update/delete association side effects. Verification for this docs-only checkpoint: `git diff --check`; next implementation commit is `feat(labels): align chatwoot label payloads`.
 - 2026-06-05: Phase 2/3 account settings checkpoint prepared as `feat(accounts): align account payloads`; audited Chatwoot `AccountsController`, `_account.json.jbuilder`, account create/show/update views, dashboard `account.js`, account Vuex store, and account settings components. Account show/update/settings now return raw Chatwoot account objects with settings, features, custom attributes, cache keys, locale/name/domain/status/support fields instead of local success/data envelopes. Account creation now accepts Chatwoot `account_name` and returns `{ data: { account_id } }` for the add-account modal. `update_active_at` returns empty `200 OK`, and `cache_keys` returns `{ cache_keys: { label, inbox, team } }` with zero-epoch defaults. Focused account handler/service tests, combined handler/service/router tests, full `go test ./...`, and `git diff --check` passed; continue account users/invitations/permissions drift and Phase 6 placeholder audit next.
 - 2026-06-05: Phase 2/3 settings/inbox assignment checkpoint prepared as `feat(settings): align assignable agents payloads`; audited Chatwoot `AssignableAgentsController#index`, inbox `assignable_agents` view, `_agent.json.jbuilder`, and reused dashboard assignable-agent API/store consumers. Assignable-agent endpoints now return Chatwoot `{ payload: [...] }` instead of local success/data envelopes, serialize the same agent fields used by conversation assignment UI, and source role, availability, auto-offline, and custom-role data from the account membership. Focused handler/service tests, combined handler/service/router tests, full `go test ./...`, and `git diff --check` passed; continue account users/invitations/permissions drift and Phase 6 placeholder audit next.
diff --git a/internal/handler/api/v1/helpers.go b/internal/handler/api/v1/helpers.go
index 621ed936..5eba1cd7 100644
--- a/internal/handler/api/v1/helpers.go
+++ b/internal/handler/api/v1/helpers.go
@@ -11,6 +11,9 @@ import (
 )
 
 func bindJSONWrappedOrRaw(c *gin.Context, wrapperKey string, target any) error {
+	if c.Request.Body == nil {
+		return fmt.Errorf("empty request body")
+	}
 	body, err := io.ReadAll(c.Request.Body)
 	if err != nil {
 		return err
diff --git a/internal/handler/api/v1/label_handler.go b/internal/handler/api/v1/label_handler.go
index 13d897c4..10a986ff 100644
--- a/internal/handler/api/v1/label_handler.go
+++ b/internal/handler/api/v1/label_handler.go
@@ -5,6 +5,7 @@ import (
 	"strconv"
 
 	"github.com/gin-gonic/gin"
+	"github.com/gochat/gochat/internal/model"
 	"github.com/gochat/gochat/internal/service"
 	applogger "github.com/gochat/gochat/pkg/logger"
 	"github.com/gochat/gochat/pkg/response"
@@ -31,15 +32,11 @@ func (h *LabelHandler) CreateTag(c *gin.Context) {
 		return
 	}
 
-	// Chatwoot: params.require(:label) → {"label": {...}}
-	var wrapper struct {
-		Label service.CreateTagRequest `json:"label"`
-	}
-	if err := c.ShouldBindJSON(&wrapper); err != nil {
+	var req service.CreateTagRequest
+	if err := bindJSONWrappedOrRaw(c, "label", &req); err != nil {
 		response.AbortWithStatusError(c, http.StatusBadRequest, response.ErrValidation, err.Error())
 		return
 	}
-	req := wrapper.Label
 
 	tag, err := h.tagSvc.Create(c.Request.Context(), accountID, &req)
 	if err != nil {
@@ -48,26 +45,31 @@ func (h *LabelHandler) CreateTag(c *gin.Context) {
 		return
 	}
 
-	response.Created(c, tag)
+	c.JSON(http.StatusOK, serializeLabel(tag))
 }
 
 // GetTag retrieves a tag by ID.
 // GET /api/v1/accounts/:account_id/tags/:tag_id
 func (h *LabelHandler) GetTag(c *gin.Context) {
+	accountID, err := parseUintParam(c, "account_id")
+	if err != nil {
+		response.AbortWithStatusError(c, http.StatusBadRequest, response.ErrBadRequest, "invalid account_id")
+		return
+	}
 	tagID, err := parseUintParam(c, "tag_id")
 	if err != nil {
 		response.AbortWithStatusError(c, http.StatusBadRequest, response.ErrBadRequest, "invalid tag_id")
 		return
 	}
 
-	tag, err := h.tagSvc.GetByID(c.Request.Context(), tagID)
+	tag, err := h.tagSvc.GetByIDAndAccountID(c.Request.Context(), accountID, tagID)
 	if err != nil {
 		applogger.L().Errorf("Get tag: %v", err)
 		handleServiceError(c, err)
 		return
 	}
 
-	response.OK(c, tag)
+	c.JSON(http.StatusOK, serializeLabel(tag))
 }
 
 // ListTags returns all tags in an account.
@@ -86,27 +88,34 @@ func (h *LabelHandler) ListTags(c *gin.Context) {
 		return
 	}
 
-	response.OK(c, tags)
+	c.JSON(http.StatusOK, gin.H{"payload": serializeLabels(tags)})
 }
 
 // UpdateTag modifies an existing tag.
 // PUT /api/v1/accounts/:account_id/tags/:tag_id
 func (h *LabelHandler) UpdateTag(c *gin.Context) {
+	accountID, err := parseUintParam(c, "account_id")
+	if err != nil {
+		response.AbortWithStatusError(c, http.StatusBadRequest, response.ErrBadRequest, "invalid account_id")
+		return
+	}
 	tagID, err := parseUintParam(c, "tag_id")
 	if err != nil {
 		response.AbortWithStatusError(c, http.StatusBadRequest, response.ErrBadRequest, "invalid tag_id")
 		return
 	}
 
-	// Chatwoot: params.require(:label) → {"label": {...}}
-	var wrapper struct {
-		Label service.UpdateTagRequest `json:"label"`
+	if _, err := h.tagSvc.GetByIDAndAccountID(c.Request.Context(), accountID, tagID); err != nil {
+		applogger.L().Errorf("Get tag for update: %v", err)
+		handleServiceError(c, err)
+		return
 	}
-	if err := c.ShouldBindJSON(&wrapper); err != nil {
+
+	var req service.UpdateTagRequest
+	if err := bindJSONWrappedOrRaw(c, "label", &req); err != nil {
 		response.AbortWithStatusError(c, http.StatusBadRequest, response.ErrValidation, err.Error())
 		return
 	}
-	req := wrapper.Label
 
 	tag, err := h.tagSvc.Update(c.Request.Context(), tagID, &req)
 	if err != nil {
@@ -115,25 +124,61 @@ func (h *LabelHandler) UpdateTag(c *gin.Context) {
 		return
 	}
 
-	response.OK(c, tag)
+	c.JSON(http.StatusOK, serializeLabel(tag))
 }
 
 // DeleteTag soft-deletes a tag.
 // DELETE /api/v1/accounts/:account_id/tags/:tag_id
 func (h *LabelHandler) DeleteTag(c *gin.Context) {
+	accountID, err := parseUintParam(c, "account_id")
+	if err != nil {
+		response.AbortWithStatusError(c, http.StatusBadRequest, response.ErrBadRequest, "invalid account_id")
+		return
+	}
 	tagID, err := parseUintParam(c, "tag_id")
 	if err != nil {
 		response.AbortWithStatusError(c, http.StatusBadRequest, response.ErrBadRequest, "invalid tag_id")
 		return
 	}
 
+	if _, err := h.tagSvc.GetByIDAndAccountID(c.Request.Context(), accountID, tagID); err != nil {
+		applogger.L().Errorf("Get tag for delete: %v", err)
+		handleServiceError(c, err)
+		return
+	}
+
 	if err := h.tagSvc.Delete(c.Request.Context(), tagID); err != nil {
 		applogger.L().Errorf("Delete tag: %v", err)
 		handleServiceError(c, err)
 		return
 	}
 
-	response.NoContent(c)
+	c.Status(http.StatusOK)
+}
+
+func serializeLabels(tags []model.Tag) []gin.H {
+	payload := make([]gin.H, 0, len(tags))
+	for i := range tags {
+		payload = append(payload, serializeLabel(&tags[i]))
+	}
+	return payload
+}
+
+func serializeLabel(tag *model.Tag) gin.H {
+	return gin.H{
+		"id":              tag.ID,
+		"title":           tag.Name,
+		"description":     tag.Description,
+		"color":           tag.Color,
+		"show_on_sidebar": labelShowOnSidebar(tag),
+	}
+}
+
+func labelShowOnSidebar(tag *model.Tag) bool {
+	if tag.ShowOnSidebar == nil {
+		return false
+	}
+	return *tag.ShowOnSidebar
 }
 
 // ========== Conversation-Label Association ==========
@@ -327,9 +372,9 @@ func (h *LabelHandler) GetConversationsByTag(c *gin.Context) {
 	}
 
 	response.OK(c, gin.H{
-		"labels": labels,
-		"count":  count,
-		"page":   page,
+		"labels":   labels,
+		"count":    count,
+		"page":     page,
 		"per_page": perPage,
 	})
-}
\ No newline at end of file
+}
diff --git a/internal/handler/api/v1/label_handler_test.go b/internal/handler/api/v1/label_handler_test.go
index ec23f3fb..1364a67f 100644
--- a/internal/handler/api/v1/label_handler_test.go
+++ b/internal/handler/api/v1/label_handler_test.go
@@ -33,7 +33,7 @@ func (s *LabelHandlerTestSuite) SetupSuite() {
 		Logger: logger.Default.LogMode(logger.Silent),
 	})
 	s.Require().NoError(err)
-	s.Require().NoError(db.AutoMigrate(&model.Account{}, &model.User{}, &model.Tag{}, &model.ConversationLabel{}, &model.Conversation{}, &model.Inbox{}, &model.Contact{}))
+	s.Require().NoError(db.AutoMigrate(&model.Account{}, &model.User{}, &model.Tag{}, &model.ConversationLabel{}, &model.ContactLabel{}, &model.Conversation{}, &model.Inbox{}, &model.Contact{}))
 	s.db = db
 
 	convLabelRepo := repository.NewConversationLabelRepo(db)
@@ -57,15 +57,31 @@ func TestLabelHandlerSuite(t *testing.T) {
 	suite.Run(t, new(LabelHandlerTestSuite))
 }
 
+func labelBoolPtr(v bool) *bool { return &v }
+
+func (s *LabelHandlerTestSuite) SetupTest() {
+	s.Require().NoError(s.db.Exec("DELETE FROM conversation_labels").Error)
+	s.Require().NoError(s.db.Exec("DELETE FROM contact_labels").Error)
+	s.Require().NoError(s.db.Unscoped().Where("account_id = ?", s.account.ID).Delete(&model.Tag{}).Error)
+}
+
 func (s *LabelHandlerTestSuite) TestListTags_Success() {
 	r := gin.New()
 	r.GET("/api/v1/accounts/:account_id/tags", s.handler.ListTags)
+	s.Require().NoError(s.db.Create(&model.Tag{AccountID: s.account.ID, Name: "billing", Color: "#ff0000", Description: "Billing issues", ShowOnSidebar: labelBoolPtr(true)}).Error)
 
 	w := httptest.NewRecorder()
 	req, _ := http.NewRequest("GET", fmt.Sprintf("/api/v1/accounts/%d/tags", s.account.ID), nil)
 	r.ServeHTTP(w, req)
 
 	assert.Equal(s.T(), http.StatusOK, w.Code)
+	var resp map[string][]map[string]interface{}
+	s.Require().NoError(json.Unmarshal(w.Body.Bytes(), &resp))
+	s.Require().Len(resp["payload"], 1)
+	assert.Equal(s.T(), "billing", resp["payload"][0]["title"])
+	assert.Equal(s.T(), "Billing issues", resp["payload"][0]["description"])
+	assert.Equal(s.T(), "#ff0000", resp["payload"][0]["color"])
+	assert.Equal(s.T(), true, resp["payload"][0]["show_on_sidebar"])
 }
 
 func (s *LabelHandlerTestSuite) TestCreateTag_BadRequest_EmptyBody() {
@@ -81,10 +97,31 @@ func (s *LabelHandlerTestSuite) TestCreateTag_BadRequest_EmptyBody() {
 }
 
 func (s *LabelHandlerTestSuite) TestCreateTag_Success() {
+	r := gin.New()
+	r.POST("/api/v1/accounts/:account_id/labels", s.handler.CreateTag)
+
+	body := map[string]interface{}{"label": map[string]interface{}{"title": "Priority", "description": "Hot queue", "color": "#FF0000", "show_on_sidebar": false}}
+	b, _ := json.Marshal(body)
+
+	w := httptest.NewRecorder()
+	req, _ := http.NewRequest("POST", fmt.Sprintf("/api/v1/accounts/%d/labels", s.account.ID), bytes.NewBuffer(b))
+	req.Header.Set("Content-Type", "application/json")
+	r.ServeHTTP(w, req)
+
+	assert.Equal(s.T(), http.StatusOK, w.Code)
+	var resp map[string]interface{}
+	s.Require().NoError(json.Unmarshal(w.Body.Bytes(), &resp))
+	assert.Equal(s.T(), "priority", resp["title"])
+	assert.Equal(s.T(), "Hot queue", resp["description"])
+	assert.Equal(s.T(), "#FF0000", resp["color"])
+	assert.Equal(s.T(), false, resp["show_on_sidebar"])
+}
+
+func (s *LabelHandlerTestSuite) TestCreateTag_RawNameCompatibility() {
 	r := gin.New()
 	r.POST("/api/v1/accounts/:account_id/tags", s.handler.CreateTag)
 
-	body := map[string]interface{}{"name": "priority", "color": "#FF0000"}
+	body := map[string]interface{}{"name": "legacy", "color": ""}
 	b, _ := json.Marshal(body)
 
 	w := httptest.NewRecorder()
@@ -92,7 +129,59 @@ func (s *LabelHandlerTestSuite) TestCreateTag_Success() {
 	req.Header.Set("Content-Type", "application/json")
 	r.ServeHTTP(w, req)
 
-	assert.Equal(s.T(), http.StatusCreated, w.Code)
+	assert.Equal(s.T(), http.StatusOK, w.Code)
+	var resp map[string]interface{}
+	s.Require().NoError(json.Unmarshal(w.Body.Bytes(), &resp))
+	assert.Equal(s.T(), "legacy", resp["title"])
+	assert.Equal(s.T(), "#1f93ff", resp["color"])
+	assert.Equal(s.T(), true, resp["show_on_sidebar"])
+}
+
+func (s *LabelHandlerTestSuite) TestUpdateTag_ChatwootPayloadAndAccountScope() {
+	r := gin.New()
+	r.PUT("/api/v1/accounts/:account_id/labels/:tag_id", s.handler.UpdateTag)
+	tag := &model.Tag{AccountID: s.account.ID, Name: "old", Color: "#000000", ShowOnSidebar: labelBoolPtr(true)}
+	s.Require().NoError(s.db.Create(tag).Error)
+
+	desc := "New description"
+	color := "#00ff00"
+	show := false
+	body := map[string]interface{}{"label": map[string]interface{}{"title": "New", "description": desc, "color": color, "show_on_sidebar": show}}
+	b, _ := json.Marshal(body)
+
+	w := httptest.NewRecorder()
+	req, _ := http.NewRequest("PUT", fmt.Sprintf("/api/v1/accounts/%d/labels/%d", s.account.ID, tag.ID), bytes.NewBuffer(b))
+	req.Header.Set("Content-Type", "application/json")
+	r.ServeHTTP(w, req)
+
+	assert.Equal(s.T(), http.StatusOK, w.Code)
+	var resp map[string]interface{}
+	s.Require().NoError(json.Unmarshal(w.Body.Bytes(), &resp))
+	assert.Equal(s.T(), "new", resp["title"])
+	assert.Equal(s.T(), desc, resp["description"])
+	assert.Equal(s.T(), color, resp["color"])
+	assert.Equal(s.T(), show, resp["show_on_sidebar"])
+}
+
+func (s *LabelHandlerTestSuite) TestDeleteTag_ReturnsOKAndRemovesAssociations() {
+	r := gin.New()
+	r.DELETE("/api/v1/accounts/:account_id/labels/:tag_id", s.handler.DeleteTag)
+	tag := &model.Tag{AccountID: s.account.ID, Name: "old", Color: "#000000", ShowOnSidebar: labelBoolPtr(true)}
+	s.Require().NoError(s.db.Create(tag).Error)
+	s.Require().NoError(s.db.Create(&model.ConversationLabel{AccountID: s.account.ID, ConversationID: 10, TagID: tag.ID}).Error)
+	s.Require().NoError(s.db.Create(&model.ContactLabel{AccountID: s.account.ID, ContactID: 20, TagID: tag.ID}).Error)
+
+	w := httptest.NewRecorder()
+	req, _ := http.NewRequest("DELETE", fmt.Sprintf("/api/v1/accounts/%d/labels/%d", s.account.ID, tag.ID), nil)
+	r.ServeHTTP(w, req)
+
+	assert.Equal(s.T(), http.StatusOK, w.Code)
+	var convCount int64
+	s.Require().NoError(s.db.Model(&model.ConversationLabel{}).Where("tag_id = ?", tag.ID).Count(&convCount).Error)
+	assert.Equal(s.T(), int64(0), convCount)
+	var contactCount int64
+	s.Require().NoError(s.db.Model(&model.ContactLabel{}).Where("tag_id = ?", tag.ID).Count(&contactCount).Error)
+	assert.Equal(s.T(), int64(0), contactCount)
 }
 
 func (s *LabelHandlerTestSuite) TestGetTag_BadRequest_InvalidID() {
@@ -196,4 +285,4 @@ func (s *LabelHandlerTestSuite) TestBatchRemoveLabel_BadRequest_InvalidAccountID
 	r.ServeHTTP(w, req)
 
 	assert.Equal(s.T(), http.StatusBadRequest, w.Code)
-}
\ No newline at end of file
+}
diff --git a/internal/model/tag.go b/internal/model/tag.go
index 6ecea95b..df3a657b 100644
--- a/internal/model/tag.go
+++ b/internal/model/tag.go
@@ -10,15 +10,17 @@ import (
 // Reference: Chatwoot Tag + Taggings merged + P2B M4 spec
 // Each tag belongs to an account and has a unique name within that account.
 type Tag struct {
-	ID        uint           `gorm:"primaryKey;autoIncrement" json:"id"`
-	AccountID uint           `gorm:"not null;uniqueIndex:idx_tag_account_name" json:"account_id"`
-	Name      string         `gorm:"size:255;not null;uniqueIndex:idx_tag_account_name" json:"name"`
-	Color     string         `gorm:"size:50" json:"color,omitempty"`
-	CreatedAt time.Time      `gorm:"autoCreateTime" json:"created_at"`
-	UpdatedAt time.Time      `gorm:"autoUpdateTime" json:"updated_at"`
-	DeletedAt gorm.DeletedAt `gorm:"index" json:"deleted_at,omitempty"`
+	ID            uint           `gorm:"primaryKey;autoIncrement" json:"id"`
+	AccountID     uint           `gorm:"not null;uniqueIndex:idx_tag_account_name" json:"account_id"`
+	Name          string         `gorm:"size:255;not null;uniqueIndex:idx_tag_account_name" json:"name"`
+	Color         string         `gorm:"size:50;not null;default:#1f93ff" json:"color,omitempty"`
+	Description   string         `gorm:"type:text" json:"description,omitempty"`
+	ShowOnSidebar *bool          `json:"show_on_sidebar"`
+	CreatedAt     time.Time      `gorm:"autoCreateTime" json:"created_at"`
+	UpdatedAt     time.Time      `gorm:"autoUpdateTime" json:"updated_at"`
+	DeletedAt     gorm.DeletedAt `gorm:"index" json:"deleted_at,omitempty"`
 
 	Account Account `gorm:"foreignKey:AccountID" json:"account,omitempty"`
 }
 
-func (Tag) TableName() string { return "tags" }
\ No newline at end of file
+func (Tag) TableName() string { return "tags" }
diff --git a/internal/repository/tag_repo.go b/internal/repository/tag_repo.go
index c4cd3617..fbdf9a59 100644
--- a/internal/repository/tag_repo.go
+++ b/internal/repository/tag_repo.go
@@ -2,6 +2,7 @@ package repository
 
 import (
 	"context"
+	"strings"
 
 	"github.com/gochat/gochat/internal/model"
 	"gorm.io/gorm"
@@ -30,6 +31,15 @@ func (r *TagRepo) GetByID(ctx context.Context, id uint) (*model.Tag, error) {
 	return &tag, nil
 }
 
+// GetByIDAndAccountID retrieves a tag scoped to an account.
+func (r *TagRepo) GetByIDAndAccountID(ctx context.Context, accountID, id uint) (*model.Tag, error) {
+	var tag model.Tag
+	if err := r.db.WithContext(ctx).Where("account_id = ?", accountID).First(&tag, id).Error; err != nil {
+		return nil, err
+	}
+	return &tag, nil
+}
+
 // Update saves changes to an existing tag.
 func (r *TagRepo) Update(ctx context.Context, tag *model.Tag) error {
 	return r.db.WithContext(ctx).Save(tag).Error
@@ -40,6 +50,29 @@ func (r *TagRepo) Delete(ctx context.Context, id uint) error {
 	return r.db.WithContext(ctx).Delete(&model.Tag{}, id).Error
 }
 
+// DeleteWithAssociations removes a tag and the local association rows that point to it.
+func (r *TagRepo) DeleteWithAssociations(ctx context.Context, tag *model.Tag) error {
+	return r.db.WithContext(ctx).Transaction(func(tx *gorm.DB) error {
+		if err := tx.Where("account_id = ? AND tag_id = ?", tag.AccountID, tag.ID).Delete(&model.ConversationLabel{}).Error; err != nil {
+			return err
+		}
+		if err := tx.Where("account_id = ? AND tag_id = ?", tag.AccountID, tag.ID).Delete(&model.ContactLabel{}).Error; err != nil {
+			return err
+		}
+		if err := r.updateConversationLabelText(ctx, tx, tag.AccountID, tag.Name, ""); err != nil {
+			return err
+		}
+		return tx.Delete(&model.Tag{}, tag.ID).Error
+	})
+}
+
+// RenameConversationLabelText keeps the legacy conversations.labels field aligned with label title changes.
+func (r *TagRepo) RenameConversationLabelText(ctx context.Context, accountID uint, oldName, newName string) error {
+	return r.db.WithContext(ctx).Transaction(func(tx *gorm.DB) error {
+		return r.updateConversationLabelText(ctx, tx, accountID, oldName, newName)
+	})
+}
+
 // FindByAccountID returns all tags for an account, ordered by name.
 func (r *TagRepo) FindByAccountID(ctx context.Context, accountID uint) ([]model.Tag, error) {
 	var tags []model.Tag
@@ -75,6 +108,61 @@ func (r *TagRepo) FindByNameAndAccountID(ctx context.Context, accountID uint, na
 	return &tag, nil
 }
 
+func (r *TagRepo) updateConversationLabelText(ctx context.Context, tx *gorm.DB, accountID uint, oldName, newName string) error {
+	oldName = strings.TrimSpace(oldName)
+	newName = strings.TrimSpace(newName)
+	if oldName == "" || oldName == newName {
+		return nil
+	}
+
+	var conversations []model.Conversation
+	if err := tx.WithContext(ctx).
+		Where("account_id = ? AND labels IS NOT NULL AND labels != ''", accountID).
+		Find(&conversations).Error; err != nil {
+		return err
+	}
+	for _, conversation := range conversations {
+		updated, changed := replaceLabelName(conversation.Labels, oldName, newName)
+		if !changed {
+			continue
+		}
+		if err := tx.Model(&model.Conversation{}).Where("id = ?", conversation.ID).Update("labels", updated).Error; err != nil {
+			return err
+		}
+	}
+	return nil
+}
+
+func replaceLabelName(labels, oldName, newName string) (string, bool) {
+	parts := strings.Split(labels, ",")
+	seen := map[string]struct{}{}
+	changed := false
+	result := make([]string, 0, len(parts))
+	for _, part := range parts {
+		label := strings.TrimSpace(part)
+		if label == "" {
+			continue
+		}
+		if strings.EqualFold(label, oldName) {
+			changed = true
+			label = newName
+		}
+		if label == "" {
+			continue
+		}
+		key := strings.ToLower(label)
+		if _, ok := seen[key]; ok {
+			continue
+		}
+		seen[key] = struct{}{}
+		result = append(result, label)
+	}
+	if !changed {
+		return labels, false
+	}
+	return strings.Join(result, ","), true
+}
+
 // FindByIDs retrieves multiple tags by their IDs.
 func (r *TagRepo) FindByIDs(ctx context.Context, ids []uint) ([]model.Tag, error) {
 	var tags []model.Tag
@@ -82,4 +170,4 @@ func (r *TagRepo) FindByIDs(ctx context.Context, ids []uint) ([]model.Tag, error
 		return nil, err
 	}
 	return tags, nil
-}
\ No newline at end of file
+}
diff --git a/internal/service/tag_service.go b/internal/service/tag_service.go
index af75bc67..1eebf760 100644
--- a/internal/service/tag_service.go
+++ b/internal/service/tag_service.go
@@ -3,6 +3,7 @@ package service
 import (
 	"context"
 	"errors"
+	"strings"
 
 	"github.com/gochat/gochat/internal/model"
 	"github.com/gochat/gochat/internal/repository"
@@ -20,28 +21,52 @@ func NewTagService(repo *repository.TagRepo) *TagService {
 
 // CreateTagRequest is the DTO for creating a tag.
 type CreateTagRequest struct {
-	Name    string `json:"name" validate:"required,min=1,max=255"`
-	Color   string `json:"color"`
+	Name          string `json:"name" validate:"omitempty,min=1,max=255"`
+	Title         string `json:"title" validate:"omitempty,min=1,max=255"`
+	Description   string `json:"description"`
+	Color         string `json:"color"`
+	ShowOnSidebar *bool  `json:"show_on_sidebar"`
 }
 
 // UpdateTagRequest is the DTO for updating a tag.
 type UpdateTagRequest struct {
-	Name    string `json:"name" validate:"omitempty,min=1,max=255"`
-	Color   string `json:"color"`
+	Name          string  `json:"name" validate:"omitempty,min=1,max=255"`
+	Title         string  `json:"title" validate:"omitempty,min=1,max=255"`
+	Description   *string `json:"description"`
+	Color         *string `json:"color"`
+	ShowOnSidebar *bool   `json:"show_on_sidebar"`
 }
 
 // Create creates a new tag for the given account.
 func (s *TagService) Create(ctx context.Context, accountID uint, req *CreateTagRequest) (*model.Tag, error) {
+	name := normalizeLabelTitle(req.Title)
+	if name == "" {
+		name = normalizeLabelTitle(req.Name)
+	}
+	if name == "" {
+		return nil, errors.New("label title is required")
+	}
+	color := strings.TrimSpace(req.Color)
+	if color == "" {
+		color = "#1f93ff"
+	}
+	showOnSidebar := true
+	if req.ShowOnSidebar != nil {
+		showOnSidebar = *req.ShowOnSidebar
+	}
+
 	// Check for duplicate name within account
-	existing, err := s.repo.FindByNameAndAccountID(ctx, accountID, req.Name)
+	existing, err := s.repo.FindByNameAndAccountID(ctx, accountID, name)
 	if err == nil && existing != nil {
 		return nil, errors.New("tag name already exists in this account")
 	}
 
 	tag := &model.Tag{
-		AccountID: accountID,
-		Name:      req.Name,
-		Color:     req.Color,
+		AccountID:     accountID,
+		Name:          name,
+		Description:   req.Description,
+		Color:         color,
+		ShowOnSidebar: &showOnSidebar,
 	}
 	if err := s.repo.Create(ctx, tag); err != nil {
 		applogger.L().Errorf("Create tag: %v", err)
@@ -59,6 +84,15 @@ func (s *TagService) GetByID(ctx context.Context, id uint) (*model.Tag, error) {
 	return tag, nil
 }
 
+// GetByIDAndAccountID retrieves a tag by ID scoped to an account.
+func (s *TagService) GetByIDAndAccountID(ctx context.Context, accountID, id uint) (*model.Tag, error) {
+	tag, err := s.repo.GetByIDAndAccountID(ctx, accountID, id)
+	if err != nil {
+		return nil, err
+	}
+	return tag, nil
+}
+
 // Update modifies an existing tag.
 func (s *TagService) Update(ctx context.Context, id uint, req *UpdateTagRequest) (*model.Tag, error) {
 	tag, err := s.repo.GetByID(ctx, id)
@@ -66,34 +100,62 @@ func (s *TagService) Update(ctx context.Context, id uint, req *UpdateTagRequest)
 		return nil, errors.New("tag not found")
 	}
 
-	if req.Name != "" {
+	oldName := tag.Name
+	name := normalizeLabelTitle(req.Title)
+	if name == "" {
+		name = normalizeLabelTitle(req.Name)
+	}
+	if name != "" {
 		// Check for duplicate name within account (excluding current tag)
-		existing, err := s.repo.FindByNameAndAccountID(ctx, tag.AccountID, req.Name)
+		existing, err := s.repo.FindByNameAndAccountID(ctx, tag.AccountID, name)
 		if err == nil && existing != nil && existing.ID != id {
 			return nil, errors.New("tag name already exists in this account")
 		}
-		tag.Name = req.Name
+		tag.Name = name
 	}
-	if req.Color != "" {
-		tag.Color = req.Color
+	if req.Color != nil {
+		color := strings.TrimSpace(*req.Color)
+		if color == "" {
+			color = "#1f93ff"
+		}
+		tag.Color = color
+	}
+	if req.Description != nil {
+		tag.Description = *req.Description
+	}
+	if req.ShowOnSidebar != nil {
+		tag.ShowOnSidebar = req.ShowOnSidebar
 	}
 
 	if err := s.repo.Update(ctx, tag); err != nil {
 		applogger.L().Errorf("Update tag: %v", err)
 		return nil, err
 	}
+	if oldName != tag.Name {
+		if err := s.repo.RenameConversationLabelText(ctx, tag.AccountID, oldName, tag.Name); err != nil {
+			return nil, err
+		}
+	}
 	return tag, nil
 }
 
 // Delete removes a tag by ID.
 func (s *TagService) Delete(ctx context.Context, id uint) error {
-	if err := s.repo.Delete(ctx, id); err != nil {
+	tag, err := s.repo.GetByID(ctx, id)
+	if err != nil {
+		return err
+	}
+	if err := s.repo.DeleteWithAssociations(ctx, tag); err != nil {
 		applogger.L().Errorf("Delete tag: %v", err)
 		return err
 	}
 	return nil
 }
 
+func normalizeLabelTitle(title string) string {
+	return strings.ToLower(strings.TrimSpace(title))
+}
+
 // List returns all tags for an account.
 func (s *TagService) List(ctx context.Context, accountID uint) ([]model.Tag, error) {
 	tags, err := s.repo.FindByAccountID(ctx, accountID)
@@ -113,4 +175,4 @@ func (s *TagService) ListPaginated(ctx context.Context, accountID uint, page, pe
 		return nil, 0, err
 	}
 	return tags, count, nil
-}
\ No newline at end of file
+}
diff --git a/internal/service/tag_service_test.go b/internal/service/tag_service_test.go
new file mode 100644
index 00000000..34239b1b
--- /dev/null
+++ b/internal/service/tag_service_test.go
@@ -0,0 +1,89 @@
+package service
+
+import (
+	"context"
+	"testing"
+
+	"github.com/gochat/gochat/internal/model"
+	"github.com/gochat/gochat/internal/repository"
+	"github.com/stretchr/testify/require"
+	"gorm.io/driver/sqlite"
+	"gorm.io/gorm"
+	"gorm.io/gorm/logger"
+)
+
+func newTagServiceTestDB(t *testing.T) *gorm.DB {
+	t.Helper()
+	db, err := gorm.Open(sqlite.Open("file::memory:"), &gorm.Config{Logger: logger.Default.LogMode(logger.Silent)})
+	require.NoError(t, err)
+	require.NoError(t, db.AutoMigrate(&model.Account{}, &model.Tag{}, &model.Conversation{}, &model.ConversationLabel{}, &model.ContactLabel{}))
+	return db
+}
+
+func tagBoolPtr(v bool) *bool { return &v }
+
+func TestTagService_CreateNormalizesChatwootLabelFields(t *testing.T) {
+	db := newTagServiceTestDB(t)
+	svc := NewTagService(repository.NewTagRepo(db))
+	show := false
+
+	tag, err := svc.Create(context.Background(), 1, &CreateTagRequest{
+		Title:         "Priority",
+		Description:   "Hot queue",
+		Color:         "",
+		ShowOnSidebar: &show,
+	})
+
+	require.NoError(t, err)
+	require.Equal(t, "priority", tag.Name)
+	require.Equal(t, "Hot queue", tag.Description)
+	require.Equal(t, "#1f93ff", tag.Color)
+	require.NotNil(t, tag.ShowOnSidebar)
+	require.False(t, *tag.ShowOnSidebar)
+}
+
+func TestTagService_UpdateRenamesLegacyConversationLabelText(t *testing.T) {
+	db := newTagServiceTestDB(t)
+	svc := NewTagService(repository.NewTagRepo(db))
+	tag := &model.Tag{AccountID: 1, Name: "old", Color: "#000000", ShowOnSidebar: tagBoolPtr(true)}
+	require.NoError(t, db.Create(tag).Error)
+	conversation := &model.Conversation{AccountID: 1, InboxID: 1, ContactID: 1, ChannelType: "Channel::WebWidget", Channel: "web_widget", Labels: "old,keep"}
+	require.NoError(t, db.Create(conversation).Error)
+	desc := "Renamed"
+	color := "#123456"
+
+	updated, err := svc.Update(context.Background(), tag.ID, &UpdateTagRequest{
+		Title:       "New",
+		Description: &desc,
+		Color:       &color,
+	})
+
+	require.NoError(t, err)
+	require.Equal(t, "new", updated.Name)
+	require.Equal(t, desc, updated.Description)
+	require.Equal(t, color, updated.Color)
+	require.NoError(t, db.First(conversation, conversation.ID).Error)
+	require.Equal(t, "new,keep", conversation.Labels)
+}
+
+func TestTagService_DeleteRemovesAssociationsAndLegacyConversationText(t *testing.T) {
+	db := newTagServiceTestDB(t)
+	svc := NewTagService(repository.NewTagRepo(db))
+	tag := &model.Tag{AccountID: 1, Name: "old", Color: "#000000", ShowOnSidebar: tagBoolPtr(true)}
+	require.NoError(t, db.Create(tag).Error)
+	conversation := &model.Conversation{AccountID: 1, InboxID: 1, ContactID: 1, ChannelType: "Channel::WebWidget", Channel: "web_widget", Labels: "old,keep"}
+	require.NoError(t, db.Create(conversation).Error)
+	require.NoError(t, db.Create(&model.ConversationLabel{AccountID: 1, ConversationID: conversation.ID, TagID: tag.ID}).Error)
+	require.NoError(t, db.Create(&model.ContactLabel{AccountID: 1, ContactID: 10, TagID: tag.ID}).Error)
+
+	require.NoError(t, svc.Delete(context.Background(), tag.ID))
+
+	var convLabelCount int64
+	require.NoError(t, db.Model(&model.ConversationLabel{}).Where("tag_id = ?", tag.ID).Count(&convLabelCount).Error)
+	require.Equal(t, int64(0), convLabelCount)
+	var contactLabelCount int64
+	require.NoError(t, db.Model(&model.ContactLabel{}).Where("tag_id = ?", tag.ID).Count(&contactLabelCount).Error)
+	require.Equal(t, int64(0), contactLabelCount)
+	require.NoError(t, db.First(conversation, conversation.ID).Error)
+	require.Equal(t, "keep", conversation.Labels)
+}
diff --git a/migrations/000028_align_tags_with_chatwoot_labels.down.sql b/migrations/000028_align_tags_with_chatwoot_labels.down.sql
new file mode 100644
index 00000000..3117b879
--- /dev/null
+++ b/migrations/000028_align_tags_with_chatwoot_labels.down.sql
@@ -0,0 +1,7 @@
+DROP INDEX IF EXISTS idx_tags_account_id;
+
+ALTER TABLE tags
+    ALTER COLUMN color DROP NOT NULL,
+    ALTER COLUMN color DROP DEFAULT,
+    DROP COLUMN IF EXISTS show_on_sidebar,
+    DROP COLUMN IF EXISTS description;
diff --git a/migrations/000028_align_tags_with_chatwoot_labels.up.sql b/migrations/000028_align_tags_with_chatwoot_labels.up.sql
new file mode 100644
index 00000000..18eb5f13
--- /dev/null
+++ b/migrations/000028_align_tags_with_chatwoot_labels.up.sql
@@ -0,0 +1,26 @@
+CREATE TABLE IF NOT EXISTS tags (
+    id SERIAL PRIMARY KEY,
+    account_id INTEGER NOT NULL,
+    name VARCHAR(255) NOT NULL,
+    color VARCHAR(50) NOT NULL DEFAULT '#1f93ff',
+    description TEXT,
+    show_on_sidebar BOOLEAN,
+    created_at TIMESTAMP WITH TIME ZONE DEFAULT NOW(),
+    updated_at TIMESTAMP WITH TIME ZONE DEFAULT NOW(),
+    deleted_at TIMESTAMP WITH TIME ZONE
+);
+
+ALTER TABLE tags
+    ADD COLUMN IF NOT EXISTS description TEXT,
+    ADD COLUMN IF NOT EXISTS show_on_sidebar BOOLEAN;
+
+ALTER TABLE tags
+    ALTER COLUMN color SET DEFAULT '#1f93ff';
+
+UPDATE tags SET color = '#1f93ff' WHERE color IS NULL OR color = '';
+
+ALTER TABLE tags
+    ALTER COLUMN color SET NOT NULL;
+
+CREATE UNIQUE INDEX IF NOT EXISTS idx_tag_account_name ON tags(account_id, name) WHERE deleted_at IS NULL;
+CREATE INDEX IF NOT EXISTS idx_tags_account_id ON tags(account_id) WHERE deleted_at IS NULL;