From 0870ebb56b0677ddcc99ea052ced1d84b353a98a Mon Sep 17 00:00:00 2001
From: =?UTF-8?q?Mikael=20M=C3=B8ller?= <mikaelhm@hey.com>
Date: Tue, 7 Apr 2026 17:24:50 +0800
Subject: [PATCH] Add Quick Categorize Wizard (#1386)
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* Add Quick Categorize Wizard (iteration 1)

Adds a step-by-step wizard for bulk-categorizing uncategorized transactions
and optionally creating auto-categorization rules, reducing friction after
connecting a new bank account.

New files:
- Transaction::Grouper abstraction + ByMerchantOrName strategy (groups by
  merchant name when present, falls back to entry name; sorted by count desc)
- Transactions::CategorizesController (GET show / POST create)
- Wizard view at app/views/transactions/categorizes/show.html.erb
- Stimulus categorize_controller.js (Enter-key-to-select-first)
- Tests for grouper and controller

Modified files:
- routes.rb: resource :categorize inside namespace :transactions
- transactions_controller.rb: expose @uncategorized_count to index
- transactions/index.html.erb: Categorize (N) button in header
- family.rb: uncategorized_transaction_count query
- rules_controller.rb: return_to param support for wizard → rule editor flow
- rules/_form.html.erb, rules/new.html.erb: pass return_to through form
- i18n: categorizes show/create keys + rules.create.success

Co-Authored-By: Claude Sonnet 4.6 <noreply@anthropic.com>

* Quick Categorize Wizard — iteration 2 polish

Six improvements from live testing:

- Breadcrumb: Home > Transactions > Categorize
- Layout: category picker + confirmation dialog above transaction list
- Inline confirmation dialog: clicking a category pill shows a <dialog>
  summarising what will happen (N transactions → category, rule if checked)
  with Confirm and Cancel buttons — no redirect to rule editor
- Direct rule creation: rule created with active: true in the controller
  instead of redirecting to the rule editor; revert return_to plumbing from
  RulesController, rules/_form, rules/new, rules/en.yml
- Individual row assignment: per-row category <select> submits via
  PATCH /transactions/categorize/assign_entry and removes the row via
  Turbo Stream (assign_entry action + route)
- Enter key guard: selectFirst only fires when exactly 1 pill is visible
  after filtering

Co-Authored-By: Claude Sonnet 4.6 <noreply@anthropic.com>

* Quick Categorize Wizard — iteration 3 reliability fixes and UX polish

- Fix Stimulus controller not loading: remove invalid `@hotwired/turbo` named
  import (not in importmap); use global `Turbo.renderStreamMessage` instead
- Fix Enter key submitting form with wrong category when search field is
  unfocused: move keydown listener to document so it fires regardless of focus
- Prevent Enter from submitting when multiple categories are visible
- Clear search filter after bulk category assignment (pill click or Enter),
  but not after individual row dropdown assignment
- Update group transaction count and total amount live as entries are assigned
  via row dropdown or partial bulk assignment
- Add turbo frames for remaining count and group summary so they update
  without a full page reload

Co-Authored-By: Claude Sonnet 4.6 <noreply@anthropic.com>

* Quick categorization polish

* refactoring

* Remove unused GROUPS_PER_BATCH constant, fix ERB self-closing tags

Wizard only ever uses one group at a time so limit: 1 is correct and
more honest than fetching 20 and discarding 19. ERB linter fixes are
whitespace/void-element corrections with no functional change.

Co-Authored-By: Claude Sonnet 4.6 <noreply@anthropic.com>

* Move Categorize button into ... menu on transactions index

Reduces header clutter by putting it in the overflow menu at the bottom,
where it only appears when there are uncategorized transactions.

Co-Authored-By: Claude Sonnet 4.6 <noreply@anthropic.com>

* Scope categorize wizard to accessible entries only

Fixes a security issue where users with restricted account access via
account sharing could view and categorize transactions from accounts
they cannot access through normal transaction flows.

- Pass Current.accessible_entries to Transaction::Grouper so the wizard
  only displays groups from accounts the user can see
- Use Current.accessible_entries on all write paths in create and
  assign_entry, matching the pattern in TransactionCategoriesController
- Refactor Grouper to accept an entries scope instead of a family object,
  keeping authorization concerns in the controller
- Add tests verifying inaccessible entries are hidden from the wizard
  and cannot be categorized via forged POST/PATCH params

Co-Authored-By: Claude Sonnet 4.6 <noreply@anthropic.com>

* Clamp position param to >= 0 to guard against negative offset

Prevents ArgumentError from Array#drop when a negative position is
passed via a tampered query string or form value.

Co-Authored-By: Claude Sonnet 4.6 <noreply@anthropic.com>

* Surface rule creation failure and add accessible names to entry row

- Capture Rule.create_from_grouping! return value; set flash[:alert] when
  nil so users who checked "Create Rule" know it wasn't created (e.g. a
  duplicate already exists); stream the notification for partial updates
- Add aria-label to the per-row checkbox and category select in
  _entry_row so screen readers can identify which transaction each
  control belongs to

Co-Authored-By: Claude Sonnet 4.6 <noreply@anthropic.com>

* Localize breadcrumb labels in categorizes controller

Follows the pattern used by FamilyExportsController and ImportsController.
Adds 'transactions' and 'categorize' keys to the breadcrumbs locale file.

Co-Authored-By: Claude Sonnet 4.6 <noreply@anthropic.com>

* Add error handling to categorize controller fetch calls

Check response.ok before parsing the body and add .catch handlers
so network failures and non-2xx responses are logged rather than
silently swallowed. On assignment failure the per-row select is
reset to empty so the user can retry.

Co-Authored-By: Claude Sonnet 4.6 <noreply@anthropic.com>

* Scope preview_rule to accessible entries only

Entry.uncategorized_matching now accepts an entries scope instead of a
family object, matching the same pattern used for Transaction::Grouper.
The preview_rule action passes Current.accessible_entries so rule
previews respect account sharing permissions.

Co-Authored-By: Claude Sonnet 4.6 <noreply@anthropic.com>

* Scope remaining count to accessible entries

Adds Entry.uncategorized_count(entries) following the same pattern as
uncategorized_matching. Replaces all three uses of
Current.family.uncategorized_transaction_count in the categorize
controller so the remaining-count badge reflects only the transactions
the current user can actually access and categorize.

Co-Authored-By: Claude Sonnet 4.6 <noreply@anthropic.com>

* Comments got separated from their function

* Remove quick-categorize-wizard dev notes

This was a planning document used during development, not intended
for the final branch.

Co-Authored-By: Claude Sonnet 4.6 <noreply@anthropic.com>

* Recompute remaining entries from server state after writes

Adds uncategorized_entries_for helper that reloads remaining entries
from the DB with a category_id IS NULL filter after each write, so
the partial-update Turbo Stream reflects server-side state rather than
trusting the client-provided remaining_ids. This handles the case where
a concurrent request has categorized one of the remaining entries
between page render and form submit.

Co-Authored-By: Claude Sonnet 4.6 <noreply@anthropic.com>

* Rename create_from_grouping! to create_from_grouping

The method rescues RecordInvalid and returns nil, which contradicts
the bang convention. Dropping the ! correctly signals that callers
should check the return value.

Co-Authored-By: Claude Sonnet 4.6 <noreply@anthropic.com>

* Clamp offset in grouper to guard against negative values

The controller already clamps position before passing it as offset,
but clamping in the grouper itself prevents ArgumentError from
Array#drop if the grouper is ever called directly with a negative offset.

Co-Authored-By: Claude Sonnet 4.6 <noreply@anthropic.com>

---------

Co-authored-by: Claude Sonnet 4.6 <noreply@anthropic.com>
Co-authored-by: Juan José Mata <jjmata@jjmata.com>
---
 .../transactions/categorizes_controller.rb    | 131 +++++++++
 app/controllers/transactions_controller.rb    |   2 +
 .../controllers/categorize_controller.js      | 165 +++++++++++
 app/models/entry.rb                           |  37 +++
 app/models/family.rb                          |  11 +
 app/models/rule.rb                            |  13 +
 app/models/transaction/grouper.rb             |  17 ++
 .../grouper/by_merchant_or_name.rb            |  53 ++++
 .../categorizes/_entry_row.html.erb           |  20 ++
 .../categorizes/_group_summary.html.erb       |   7 +
 .../categorizes/_group_title.html.erb         |  10 +
 .../categorizes/_remaining_count.html.erb     |   5 +
 .../categorizes/_transaction_list.html.erb    |  20 ++
 .../transactions/categorizes/show.html.erb    | 145 ++++++++++
 app/views/transactions/index.html.erb         |   3 +
 config/locales/breadcrumbs/en.yml             |   2 +
 config/locales/views/transactions/en.yml      |  36 +++
 config/routes.rb                              |   4 +
 db/schema.rb                                  |   8 +-
 .../categorizes_controller_test.rb            | 268 ++++++++++++++++++
 .../grouper/by_merchant_or_name_test.rb       | 140 +++++++++
 21 files changed, 1090 insertions(+), 7 deletions(-)
 create mode 100644 app/controllers/transactions/categorizes_controller.rb
 create mode 100644 app/javascript/controllers/categorize_controller.js
 create mode 100644 app/models/transaction/grouper.rb
 create mode 100644 app/models/transaction/grouper/by_merchant_or_name.rb
 create mode 100644 app/views/transactions/categorizes/_entry_row.html.erb
 create mode 100644 app/views/transactions/categorizes/_group_summary.html.erb
 create mode 100644 app/views/transactions/categorizes/_group_title.html.erb
 create mode 100644 app/views/transactions/categorizes/_remaining_count.html.erb
 create mode 100644 app/views/transactions/categorizes/_transaction_list.html.erb
 create mode 100644 app/views/transactions/categorizes/show.html.erb
 create mode 100644 test/controllers/transactions/categorizes_controller_test.rb
 create mode 100644 test/models/transaction/grouper/by_merchant_or_name_test.rb

diff --git a/app/controllers/transactions/categorizes_controller.rb b/app/controllers/transactions/categorizes_controller.rb
new file mode 100644
index 000000000..38a505029
--- /dev/null
+++ b/app/controllers/transactions/categorizes_controller.rb
@@ -0,0 +1,131 @@
+class Transactions::CategorizesController < ApplicationController
+  def show
+    @breadcrumbs = [
+      [ t("breadcrumbs.home"), root_path ],
+      [ t("breadcrumbs.transactions"), transactions_path ],
+      [ t("breadcrumbs.categorize"), nil ]
+    ]
+    @position = [ params[:position].to_i, 0 ].max
+    groups = Transaction::Grouper.strategy.call(
+      Current.accessible_entries,
+      limit: 1,
+      offset: @position
+    )
+
+    if groups.empty?
+      redirect_to transactions_path, notice: t(".all_done") and return
+    end
+
+    @group      = groups.first
+    @categories = Current.family.categories.alphabetically
+    @total_uncategorized = Entry.uncategorized_count(Current.accessible_entries)
+  end
+
+  def create
+    @position     = params[:position].to_i
+    entry_ids     = Array.wrap(params[:entry_ids]).reject(&:blank?)
+    all_entry_ids = Array.wrap(params[:all_entry_ids]).reject(&:blank?)
+    remaining_ids = all_entry_ids - entry_ids
+
+    category = Current.family.categories.find(params[:category_id])
+    entries  = Current.accessible_entries.excluding_split_parents.where(id: entry_ids)
+    count    = entries.bulk_update!({ category_id: category.id })
+
+    if params[:create_rule] == "1"
+      rule = Rule.create_from_grouping(
+        Current.family,
+        params[:grouping_key],
+        category,
+        transaction_type: params[:transaction_type]
+      )
+      flash[:alert] = t(".rule_creation_failed") if rule.nil?
+    end
+
+    respond_to do |format|
+      format.turbo_stream do
+        remaining_entries = uncategorized_entries_for(remaining_ids)
+        remaining_ids     = remaining_entries.map { |e| e.id.to_s }
+
+        if remaining_ids.empty?
+          render turbo_stream: turbo_stream.action(:redirect, transactions_categorize_path(position: @position))
+        else
+          @categories = Current.family.categories.alphabetically
+          streams = entry_ids.map { |id| turbo_stream.remove("categorize_entry_#{id}") }
+          remaining_entries.each do |entry|
+            streams << turbo_stream.replace(
+              "categorize_entry_#{entry.id}",
+              partial: "transactions/categorizes/entry_row",
+              locals: { entry: entry, categories: @categories }
+            )
+          end
+          streams << turbo_stream.replace("categorize_remaining",
+            partial: "transactions/categorizes/remaining_count",
+            locals: { total_uncategorized: Entry.uncategorized_count(Current.accessible_entries) })
+          streams << turbo_stream.replace("categorize_group_summary",
+            partial: "transactions/categorizes/group_summary",
+            locals: { entries: remaining_entries })
+          streams.concat(flash_notification_stream_items)
+          render turbo_stream: streams
+        end
+      end
+      format.html { redirect_to transactions_categorize_path(position: @position), notice: t(".categorized", count: count) }
+    end
+  end
+
+  def preview_rule
+    filter           = params[:filter].to_s.strip
+    transaction_type = params[:transaction_type].presence
+    entries          = filter.present? ? Entry.uncategorized_matching(Current.accessible_entries, filter, transaction_type) : []
+    @categories      = Current.family.categories.alphabetically
+
+    render turbo_stream: [
+      turbo_stream.replace("categorize_group_title",
+        partial: "transactions/categorizes/group_title",
+        locals: { display_name: filter.presence || "…", color: "#737373", transaction_type: transaction_type }),
+      turbo_stream.replace("categorize_group_summary",
+        partial: "transactions/categorizes/group_summary",
+        locals: { entries: entries }),
+      turbo_stream.replace("categorize_transaction_list",
+        partial: "transactions/categorizes/transaction_list",
+        locals: { entries: entries, categories: @categories })
+    ]
+  end
+
+  def assign_entry
+    entry         = Current.accessible_entries.excluding_split_parents.find(params[:entry_id])
+    category      = Current.family.categories.find(params[:category_id])
+    position      = params[:position].to_i
+    all_entry_ids = Array.wrap(params[:all_entry_ids]).reject(&:blank?)
+    remaining_ids = all_entry_ids - [ entry.id.to_s ]
+
+    Entry.where(id: entry.id).bulk_update!({ category_id: category.id })
+
+    remaining_entries = uncategorized_entries_for(remaining_ids)
+    remaining_ids     = remaining_entries.map { |e| e.id.to_s }
+
+    streams = [ turbo_stream.remove("categorize_entry_#{entry.id}") ]
+    if remaining_ids.empty?
+      streams << turbo_stream.action(:redirect, transactions_categorize_path(position: position))
+    else
+      streams << turbo_stream.replace("categorize_remaining",
+        partial: "transactions/categorizes/remaining_count",
+        locals: { total_uncategorized: Entry.uncategorized_count(Current.accessible_entries) })
+      streams << turbo_stream.replace("categorize_group_summary",
+        partial: "transactions/categorizes/group_summary",
+        locals: { entries: remaining_entries })
+    end
+    render turbo_stream: streams
+  end
+
+  private
+
+    def uncategorized_entries_for(ids)
+      return [] if ids.blank?
+      Current.accessible_entries
+        .excluding_split_parents
+        .where(id: ids)
+        .joins("INNER JOIN transactions ON transactions.id = entries.entryable_id AND entries.entryable_type = 'Transaction'")
+        .where(transactions: { category_id: nil })
+        .to_a
+    end
+end
diff --git a/app/controllers/transactions_controller.rb b/app/controllers/transactions_controller.rb
index dc79aaeb6..876e7d848 100644
--- a/app/controllers/transactions_controller.rb
+++ b/app/controllers/transactions_controller.rb
@@ -52,6 +52,8 @@ class TransactionsController < ApplicationController
       Set.new
     end
 
+    @uncategorized_count = Current.family.uncategorized_transaction_count
+
     # Load projected recurring transactions for next 10 days
     @projected_recurring = Current.family.recurring_transactions
                                   .accessible_by(Current.user)
diff --git a/app/javascript/controllers/categorize_controller.js b/app/javascript/controllers/categorize_controller.js
new file mode 100644
index 000000000..08f5a1dc7
--- /dev/null
+++ b/app/javascript/controllers/categorize_controller.js
@@ -0,0 +1,165 @@
+import { Controller } from "@hotwired/stimulus";
+
+export default class extends Controller {
+  static targets = [
+    "list",
+    "createRuleCheckbox",
+    "filterDisplay",
+    "filterEditTrigger",
+    "filterEditArea",
+    "filterInput",
+    "groupingKeyHidden",
+    "filter",
+    "ruleDetails",
+  ];
+  static values = { assignEntryUrl: String, position: Number, previewRuleUrl: String, transactionType: String };
+
+  connect() {
+    this.boundSelectFirst = this.selectFirst.bind(this);
+    document.addEventListener("keydown", this.boundSelectFirst);
+    this.toggleRuleDetails();
+  }
+
+  disconnect() {
+    document.removeEventListener("keydown", this.boundSelectFirst);
+    clearTimeout(this._previewTimer);
+  }
+
+  selectFirst(event) {
+    if (event.key !== "Enter") return;
+
+    const tag = event.target.tagName;
+    if (tag === "BUTTON" || tag === "A") return;
+
+    // Don't intercept Enter when the user is confirming an inline filter edit
+    if (this.hasFilterInputTarget && event.target === this.filterInputTarget) return;
+
+    event.preventDefault();
+
+    const visible = Array.from(
+      this.listTarget.querySelectorAll(".filterable-item")
+    ).filter((el) => el.style.display !== "none");
+
+    if (visible.length !== 1) return;
+
+    visible[0].click();
+  }
+
+  clearFilter(event) {
+    if (event.target.tagName !== "BUTTON") return;
+    if (!this.hasFilterTarget) return;
+    this.filterTarget.value = "";
+    this.filterTarget.dispatchEvent(new Event("input"));
+  }
+
+  uncheckRule() {
+    if (this.hasCreateRuleCheckboxTarget) {
+      this.createRuleCheckboxTarget.checked = false;
+      this.toggleRuleDetails();
+    }
+  }
+
+  toggleRuleDetails() {
+    if (!this.hasRuleDetailsTarget || !this.hasCreateRuleCheckboxTarget) return;
+    const enabled = this.createRuleCheckboxTarget.checked;
+    this.ruleDetailsTarget.classList.toggle("opacity-40", !enabled);
+    if (this.hasFilterInputTarget) {
+      this.filterInputTarget.disabled = !enabled;
+    }
+  }
+
+  startFilterEdit() {
+    this.filterDisplayTarget.classList.add("hidden");
+    this.filterEditTriggerTarget.classList.add("hidden");
+    this.filterEditAreaTarget.classList.remove("hidden");
+    this.filterEditAreaTarget.classList.add("flex");
+    this.filterInputTarget.focus();
+    this.filterInputTarget.select();
+  }
+
+  confirmFilterEdit(event) {
+    event.preventDefault();
+    event.stopPropagation();
+    const value = this.filterInputTarget.value.trim();
+    if (!value) return;
+
+    this.filterDisplayTarget.textContent = `"${value}"`;
+    this.groupingKeyHiddenTarget.value = value;
+
+    this.filterEditAreaTarget.classList.add("hidden");
+    this.filterEditAreaTarget.classList.remove("flex");
+    this.filterDisplayTarget.classList.remove("hidden");
+    this.filterEditTriggerTarget.classList.remove("hidden");
+
+    this._doPreviewRule(value);
+  }
+
+  cancelFilterEdit(event) {
+    event.preventDefault();
+    event.stopPropagation();
+    this.filterEditAreaTarget.classList.add("hidden");
+    this.filterEditAreaTarget.classList.remove("flex");
+    this.filterDisplayTarget.classList.remove("hidden");
+    this.filterEditTriggerTarget.classList.remove("hidden");
+  }
+
+  previewRule(event) {
+    this._doPreviewRule(event.target.value);
+  }
+
+  _doPreviewRule(filter) {
+    clearTimeout(this._previewTimer);
+    this._previewTimer = setTimeout(() => {
+      const url = new URL(this.previewRuleUrlValue, window.location.origin);
+      url.searchParams.set("filter", filter);
+      url.searchParams.set("position", this.positionValue);
+      url.searchParams.set("transaction_type", this.transactionTypeValue);
+      fetch(url.toString(), {
+        credentials: "same-origin",
+        headers: {
+          "X-CSRF-Token": document.querySelector('meta[name="csrf-token"]')?.content,
+          Accept: "text/vnd.turbo-stream.html",
+        },
+      })
+        .then((r) => { if (!r.ok) throw new Error(r.statusText); return r.text(); })
+        .then((html) => Turbo.renderStreamMessage(html))
+        .catch((err) => console.error("Rule preview failed:", err));
+    }, 300);
+  }
+
+  assignEntry(event) {
+    const select = event.target;
+    const categoryId = select.value;
+    if (!categoryId) return;
+
+    this.uncheckRule();
+
+    const entryId = select.dataset.entryId;
+    const body = new FormData();
+    body.append("entry_id", entryId);
+    body.append("category_id", categoryId);
+    body.append("position", this.positionValue);
+
+    // all_entry_ids[] hidden inputs live inside each Turbo Frame —
+    // automatically stay in sync as frames are removed
+    this.element.querySelectorAll("input[name='all_entry_ids[]']").forEach((input) => {
+      body.append("all_entry_ids[]", input.value);
+    });
+
+    fetch(this.assignEntryUrlValue, {
+      method: "PATCH",
+      credentials: "same-origin",
+      headers: {
+        "X-CSRF-Token": document.querySelector('meta[name="csrf-token"]')?.content,
+        Accept: "text/vnd.turbo-stream.html",
+      },
+      body,
+    })
+      .then((r) => { if (!r.ok) throw new Error(r.statusText); return r.text(); })
+      .then((html) => Turbo.renderStreamMessage(html))
+      .catch((err) => {
+        console.error("Entry assignment failed:", err);
+        select.value = "";
+      });
+  }
+}
diff --git a/app/models/entry.rb b/app/models/entry.rb
index 6c90114d2..2a3de89ad 100644
--- a/app/models/entry.rb
+++ b/app/models/entry.rb
@@ -91,6 +91,43 @@ class Entry < ApplicationRecord
     joins(:account).where(accounts: { family_id: family.id })
   end
 
+  # Counts uncategorized, non-transfer entries in the given scope.
+  # Used by the Quick Categorize Wizard to show the remaining count.
+  # @param entries [ActiveRecord::Relation] pre-scoped entries (caller controls authorization)
+  def self.uncategorized_count(entries)
+    entries
+      .joins(:account)
+      .joins("INNER JOIN transactions ON transactions.id = entries.entryable_id AND entries.entryable_type = 'Transaction'")
+      .where(accounts: { status: %w[draft active] })
+      .where(transactions: { category_id: nil })
+      .where.not(transactions: { kind: Transaction::TRANSFER_KINDS })
+      .where(entries: { excluded: false })
+      .count
+  end
+
+  # Returns uncategorized, non-transfer entries whose name matches the given filter string.
+  # Used by the Quick Categorize Wizard to preview which transactions a rule would affect.
+  # @param entries [ActiveRecord::Relation] pre-scoped entries (caller controls authorization)
+  def self.uncategorized_matching(entries, filter, transaction_type = nil)
+    sanitized = sanitize_sql_like(filter.gsub(/\s+/, " ").strip)
+    scope = entries
+              .joins(:account)
+                  .joins("INNER JOIN transactions ON transactions.id = entries.entryable_id AND entries.entryable_type = 'Transaction'")
+                  .where(accounts: { status: %w[draft active] })
+                  .where(transactions: { category_id: nil })
+                  .where.not(transactions: { kind: Transaction::TRANSFER_KINDS })
+                  .where(entries: { excluded: false })
+                  .where("BTRIM(REGEXP_REPLACE(entries.name, '[[:space:]]+', ' ', 'g')) ILIKE ?", "%#{sanitized}%")
+
+    scope = case transaction_type
+    when "income"  then scope.where("entries.amount < 0")
+    when "expense" then scope.where("entries.amount >= 0")
+    else scope
+    end
+
+    scope.includes(entryable: :merchant).order(entries: { date: :desc }).to_a
+  end
+
   # Auto-exclude stale pending transactions for an account
   # Called during sync to clean up pending transactions that never posted
   # @param account [Account] The account to clean up
diff --git a/app/models/family.rb b/app/models/family.rb
index f5eceb93f..2f7ad1b50 100644
--- a/app/models/family.rb
+++ b/app/models/family.rb
@@ -144,6 +144,17 @@ class Family < ApplicationRecord
     AutoMerchantDetector.new(self, transaction_ids: transaction_ids).auto_detect
   end
 
+  def uncategorized_transaction_count
+    Transaction
+      .joins("INNER JOIN entries ON entries.entryable_id = transactions.id AND entries.entryable_type = 'Transaction'")
+      .joins("INNER JOIN accounts ON accounts.id = entries.account_id")
+      .where(accounts: { family_id: id, status: %w[draft active] })
+      .where(transactions: { category_id: nil })
+      .where.not(transactions: { kind: Transaction::TRANSFER_KINDS })
+      .where(entries: { excluded: false })
+      .count
+  end
+
   def balance_sheet(user: Current.user)
     BalanceSheet.new(self, user: user)
   end
diff --git a/app/models/rule.rb b/app/models/rule.rb
index 74dbaece8..b53f80f83 100644
--- a/app/models/rule.rb
+++ b/app/models/rule.rb
@@ -40,6 +40,19 @@ class Rule < ApplicationRecord
     matching_resources_scope.count
   end
 
+  # Creates a categorization rule for the Quick Categorize Wizard.
+  # Returns the saved rule, or nil if a duplicate or invalid rule already exists.
+  def self.create_from_grouping(family, grouping_key, category, transaction_type: nil)
+    rule = family.rules.build(name: grouping_key, resource_type: "transaction", active: true)
+    rule.conditions.build(condition_type: "transaction_name", operator: "like", value: grouping_key)
+    rule.conditions.build(condition_type: "transaction_type", operator: "=", value: transaction_type) if transaction_type.present?
+    rule.actions.build(action_type: "set_transaction_category", value: category.id.to_s)
+    rule.save!
+    rule
+  rescue ActiveRecord::RecordInvalid
+    nil
+  end
+
   # Calculates total unique resources affected across multiple rules
   # This handles overlapping rules by deduplicating transaction IDs
   def self.total_affected_resource_count(rules)
diff --git a/app/models/transaction/grouper.rb b/app/models/transaction/grouper.rb
new file mode 100644
index 000000000..e55ac2573
--- /dev/null
+++ b/app/models/transaction/grouper.rb
@@ -0,0 +1,17 @@
+class Transaction::Grouper
+  Group = Data.define(:grouping_key, :display_name, :entries, :merchant, :transaction_type)
+
+  # Returns the active grouping strategy class.
+  # Change this method to swap algorithms without touching the wizard.
+  def self.strategy
+    Transaction::Grouper::ByMerchantOrName
+  end
+
+  # @param entries [ActiveRecord::Relation] pre-scoped entries to group (caller controls authorization)
+  # @param limit [Integer] max number of groups to return
+  # @param offset [Integer] number of groups to skip (for pagination)
+  # @return [Array<Group>]
+  def self.call(entries, limit: 20, offset: 0)
+    raise NotImplementedError, "#{name} must implement .call"
+  end
+end
diff --git a/app/models/transaction/grouper/by_merchant_or_name.rb b/app/models/transaction/grouper/by_merchant_or_name.rb
new file mode 100644
index 000000000..3618f65de
--- /dev/null
+++ b/app/models/transaction/grouper/by_merchant_or_name.rb
@@ -0,0 +1,53 @@
+class Transaction::Grouper::ByMerchantOrName < Transaction::Grouper
+  def self.call(entries, limit: 20, offset: 0)
+    new(entries).call(limit: limit, offset: offset)
+  end
+
+  def initialize(entries)
+    @entries = entries
+  end
+
+  def call(limit: 20, offset: 0)
+    uncategorized_entries
+      .group_by { |entry| grouping_key_for(entry) }
+      .map { |key, entries| build_group(key, entries) }
+      .sort_by { |g| [ -g.entries.size, g.display_name ] }
+      .drop([ offset, 0 ].max)
+      .first(limit)
+  end
+
+  private
+
+    attr_reader :entries
+
+    def uncategorized_entries
+      entries
+        .joins(:account)
+        .joins("INNER JOIN transactions ON transactions.id = entries.entryable_id AND entries.entryable_type = 'Transaction'")
+        .where(accounts: { status: %w[draft active] })
+        .where(transactions: { category_id: nil })
+        .where.not(transactions: { kind: Transaction::TRANSFER_KINDS })
+        .where(entries: { excluded: false })
+        .includes(entryable: :merchant)
+        .order(entries: { date: :desc })
+    end
+
+    def grouping_key_for(entry)
+      name = entry.entryable.merchant&.name.presence || entry.name
+      type = entry.amount.negative? ? "income" : "expense"
+      [ name, type ]
+    end
+
+    def build_group(key, entries)
+      name, type = key
+      merchant = entries.find { |e| e.entryable.merchant.present? }&.entryable&.merchant
+
+      Transaction::Grouper::Group.new(
+        grouping_key: name,
+        display_name: name,
+        entries: entries,
+        merchant: merchant,
+        transaction_type: type
+      )
+    end
+end
diff --git a/app/views/transactions/categorizes/_entry_row.html.erb b/app/views/transactions/categorizes/_entry_row.html.erb
new file mode 100644
index 000000000..5321079bc
--- /dev/null
+++ b/app/views/transactions/categorizes/_entry_row.html.erb
@@ -0,0 +1,20 @@
+<%= turbo_frame_tag "categorize_entry_#{entry.id}" do %>
+  <input type="hidden" name="all_entry_ids[]" value="<%= entry.id %>">
+  <div class="grid grid-cols-[1rem_1fr_5rem_6rem_6.5rem] gap-3 items-center px-5 py-3 bg-container hover:bg-container-hover">
+    <input type="checkbox" name="entry_ids[]" value="<%= entry.id %>"
+           checked class="checkbox checkbox--light shrink-0"
+           aria-label="<%= t("transactions.categorizes.entry_row.include_checkbox", name: entry.name) %>"
+           data-action="change->categorize#uncheckRule">
+    <span class="min-w-0 font-medium text-primary truncate"><%= entry.name %></span>
+    <span class="text-secondary whitespace-nowrap"><%= l(entry.date, format: :short) %></span>
+    <span class="font-medium text-right whitespace-nowrap <%= entry.amount.negative? ? "text-green-600" : "text-primary" %>">
+      <%= format_money(entry.amount_money.abs) %>
+    </span>
+    <%= select_tag "category_id",
+          options_from_collection_for_select(categories, :id, :name),
+          prompt: t("transactions.categorizes.show.assign_category_prompt"),
+          aria: { label: t("transactions.categorizes.entry_row.assign_category_select", name: entry.name) },
+          class: "w-full text-xs border border-primary rounded-lg px-1.5 py-0.5 bg-container text-secondary",
+          data: { entry_id: entry.id, action: "change->categorize#assignEntry" } %>
+  </div>
+<% end %>
diff --git a/app/views/transactions/categorizes/_group_summary.html.erb b/app/views/transactions/categorizes/_group_summary.html.erb
new file mode 100644
index 000000000..eeaa0dc14
--- /dev/null
+++ b/app/views/transactions/categorizes/_group_summary.html.erb
@@ -0,0 +1,7 @@
+<%= turbo_frame_tag "categorize_group_summary" do %>
+  <p class="text-sm text-secondary">
+    <%= t("transactions.categorizes.show.transaction_count", count: entries.size) %>
+    &middot;
+    <%= format_money(entries.sum { |e| e.amount_money.abs }) %>
+  </p>
+<% end %>
diff --git a/app/views/transactions/categorizes/_group_title.html.erb b/app/views/transactions/categorizes/_group_title.html.erb
new file mode 100644
index 000000000..948b504ac
--- /dev/null
+++ b/app/views/transactions/categorizes/_group_title.html.erb
@@ -0,0 +1,10 @@
+<%= turbo_frame_tag "categorize_group_title" do %>
+  <div class="flex items-center gap-2">
+    <h2 class="text-lg font-semibold text-primary"><%= display_name %></h2>
+    <% if transaction_type == "income" %>
+      <span class="text-xs font-medium px-1.5 py-0.5 rounded-full bg-green-100 text-green-700"><%= t("transactions.categorizes.show.type_income") %></span>
+    <% elsif transaction_type == "expense" %>
+      <span class="text-xs font-medium px-1.5 py-0.5 rounded-full bg-surface text-secondary border border-primary"><%= t("transactions.categorizes.show.type_expense") %></span>
+    <% end %>
+  </div>
+<% end %>
diff --git a/app/views/transactions/categorizes/_remaining_count.html.erb b/app/views/transactions/categorizes/_remaining_count.html.erb
new file mode 100644
index 000000000..d185e3357
--- /dev/null
+++ b/app/views/transactions/categorizes/_remaining_count.html.erb
@@ -0,0 +1,5 @@
+<%= turbo_frame_tag "categorize_remaining" do %>
+  <span class="text-sm text-secondary">
+    <%= t("transactions.categorizes.show.remaining", count: total_uncategorized) %>
+  </span>
+<% end %>
diff --git a/app/views/transactions/categorizes/_transaction_list.html.erb b/app/views/transactions/categorizes/_transaction_list.html.erb
new file mode 100644
index 000000000..d624a0e3c
--- /dev/null
+++ b/app/views/transactions/categorizes/_transaction_list.html.erb
@@ -0,0 +1,20 @@
+<%= turbo_frame_tag "categorize_transaction_list" do %>
+  <div class="bg-container-inset rounded-xl p-1 space-y-1">
+    <%# Header — same grid template and padding as each row %>
+    <div class="grid grid-cols-[1rem_1fr_5rem_6rem_6.5rem] gap-3 px-5 py-2 text-xs font-medium text-secondary uppercase tracking-wide">
+      <div></div>
+      <p><%= t("transactions.categorizes.show.col_transaction") %></p>
+      <p><%= t("transactions.categorizes.show.col_date") %></p>
+      <p class="text-right"><%= t("transactions.categorizes.show.col_amount") %></p>
+      <p><%= t("transactions.categorizes.show.col_category") %></p>
+    </div>
+    <%# Rows %>
+    <div class="shadow-border-xs rounded-lg overflow-hidden">
+      <div class="max-h-[32rem] overflow-y-auto divide-y divide-primary text-sm">
+        <% entries.each do |entry| %>
+          <%= render partial: "transactions/categorizes/entry_row", locals: { entry: entry, categories: categories } %>
+        <% end %>
+      </div>
+    </div>
+  </div>
+<% end %>
diff --git a/app/views/transactions/categorizes/show.html.erb b/app/views/transactions/categorizes/show.html.erb
new file mode 100644
index 000000000..59d49f61b
--- /dev/null
+++ b/app/views/transactions/categorizes/show.html.erb
@@ -0,0 +1,145 @@
+<%# Wizard step: categorize one group of uncategorized transactions %>
+<div class="w-full space-y-6 pb-12"
+     data-controller="categorize"
+     data-categorize-assign-entry-url-value="<%= assign_entry_transactions_categorize_path %>"
+     data-categorize-preview-rule-url-value="<%= preview_rule_transactions_categorize_path %>"
+     data-categorize-position-value="<%= @position %>"
+     data-categorize-transaction-type-value="<%= @group.transaction_type %>">
+  <%# Top bar: remaining count + skip %>
+  <div class="flex items-center justify-between">
+    <%= turbo_frame_tag "categorize_remaining" do %>
+      <span class="text-sm text-secondary">
+        <%= t(".remaining", count: @total_uncategorized) %>
+      </span>
+    <% end %>
+    <%= link_to transactions_categorize_path(position: @position + 1),
+          class: "flex items-center gap-1.5 text-sm font-medium text-secondary hover:text-primary" do %>
+      <%= t(".skip") %>
+      <%= icon("arrow-right", size: "sm") %>
+    <% end %>
+  </div>
+
+  <%# Group identity — above columns %>
+  <div>
+    <div class="flex items-center gap-3 mb-1">
+      <%= render partial: "transactions/categorizes/group_title",
+                 locals: { display_name: @group.display_name, color: @group.merchant&.color || "#737373", transaction_type: @group.transaction_type } %>
+    </div>
+    <%= turbo_frame_tag "categorize_group_summary" do %>
+      <p class="text-sm text-secondary">
+        <%= t(".transaction_count", count: @group.entries.size) %>
+        &middot;
+        <%= format_money(@group.entries.sum { |e| e.amount_money.abs }) %>
+      </p>
+    <% end %>
+  </div>
+
+  <%# Main form %>
+  <%= form_with url: transactions_categorize_path, method: :post, id: "categorize-form", class: "w-full" do |form| %>
+    <%= form.hidden_field :position, value: @position %>
+    <%= form.hidden_field :transaction_type, value: @group.transaction_type %>
+
+    <div class="grid grid-cols-[3fr_2fr] gap-4 items-start w-full">
+      <%# Left column (60%): rule creation + transaction list %>
+      <div class="space-y-4">
+        <%# Rule creation %>
+        <div class="bg-container shadow-border-xs rounded-xl p-4 space-y-3">
+          <label class="flex items-center gap-2.5 cursor-pointer">
+            <input type="checkbox" name="create_rule" value="1"
+                   <%= "checked" if @group.entries.size > 1 %>
+                   class="checkbox checkbox--light"
+                   data-categorize-target="createRuleCheckbox"
+                   data-action="change->categorize#toggleRuleDetails">
+            <span class="text-sm font-medium text-primary"><%= t(".create_rule_label") %></span>
+          </label>
+
+          <div data-categorize-target="ruleDetails" class="<%= "opacity-40" unless @group.entries.size > 1 %>">
+            <input type="hidden" name="grouping_key"
+                   value="<%= @group.grouping_key %>"
+                   data-categorize-target="groupingKeyHidden">
+
+            <p class="text-sm text-secondary leading-relaxed">
+              <%= t(".rule_description_prefix", type: t(".type_#{@group.transaction_type}").downcase) %>
+              <span class="inline-flex items-center gap-1 align-middle">
+                <span class="font-medium text-primary" data-categorize-target="filterDisplay">"<%= @group.grouping_key %>"</span>
+                <button type="button"
+                        class="text-secondary hover:text-primary transition-colors"
+                        data-action="click->categorize#startFilterEdit"
+                        data-categorize-target="filterEditTrigger">
+                  <%= icon("pencil", size: "sm") %>
+                </button>
+                <span class="hidden items-center gap-1" data-categorize-target="filterEditArea">
+                  <input type="text" value="<%= @group.grouping_key %>"
+                         autocomplete="off"
+                         class="text-sm border border-primary rounded-lg px-2 py-0.5 bg-container focus:outline-none focus:ring-1 focus:ring-offset-0 w-36 shadow-md"
+                         data-categorize-target="filterInput"
+                         data-action="keydown.enter->categorize#confirmFilterEdit keydown.escape->categorize#cancelFilterEdit">
+                  <button type="button"
+                          class="flex items-center justify-center w-6 h-6 rounded-md bg-primary text-inverted hover:opacity-80 transition-opacity shrink-0"
+                          data-action="click->categorize#confirmFilterEdit">
+                    <%= icon("check", size: "sm") %>
+                  </button>
+                </span>
+              </span>
+              <%= t(".rule_description_suffix") %>
+            </p>
+          </div>
+        </div>
+
+        <%# Transaction list %>
+        <div class="bg-container rounded-xl shadow-border-xs p-4 space-y-3">
+          <p class="text-xs text-secondary"><%= t(".transactions_hint") %></p>
+          <%= render partial: "transactions/categorizes/transaction_list",
+                     locals: { entries: @group.entries, categories: @categories } %>
+        </div>
+      </div>
+
+      <%# Right column (40%): category picker %>
+      <div>
+        <div class="bg-container shadow-border-xs rounded-xl p-4 space-y-3">
+          <p class="text-sm font-medium text-secondary"><%= t(".assign_category") %></p>
+
+          <div data-controller="list-filter" class="space-y-3">
+            <%# Search field %>
+            <div class="relative flex items-center bg-container border border-primary rounded-lg">
+              <%= icon("search", class: "absolute left-3 text-secondary") %>
+              <input type="text"
+                     placeholder="<%= t(".filter_placeholder") %>"
+                     autocomplete="off"
+                     autofocus
+                     class="w-full pl-9 pr-3 py-2 text-sm bg-transparent border-none rounded-lg focus:outline-none focus:ring-0 placeholder:text-secondary"
+                     data-list-filter-target="input"
+                     data-categorize-target="filter"
+                     data-action="input->list-filter#filter">
+            </div>
+
+            <%# Category pills — submit the form directly %>
+            <div data-list-filter-target="list" data-categorize-target="list"
+                 data-action="click->categorize#clearFilter"
+                 class="flex flex-wrap gap-2">
+              <p class="hidden text-sm text-secondary w-full py-2" data-list-filter-target="emptyMessage">
+                <%= t(".no_categories") %>
+              </p>
+              <% @categories.each do |category| %>
+                <button type="submit"
+                        name="category_id"
+                        value="<%= category.id %>"
+                        class="filterable-item flex items-center gap-1 text-sm font-medium rounded-full px-2.5 py-1 border cursor-pointer hover:opacity-80 transition-opacity focus:outline-none focus:ring-2 focus:ring-offset-1"
+                        style="background-color: color-mix(in oklab, <%= category.color %> 10%, transparent);
+                               border-color: color-mix(in oklab, <%= category.color %> 20%, transparent);
+                               color: <%= category.color %>;"
+                        data-filter-name="<%= category.name %>">
+                  <% if category.lucide_icon.present? %>
+                    <%= icon(category.lucide_icon, size: "sm", color: "current") %>
+                  <% end %>
+                  <%= category.name %>
+                </button>
+              <% end %>
+            </div>
+          </div>
+        </div>
+      </div>
+    </div>
+
+  <% end %>
+</div>
diff --git a/app/views/transactions/index.html.erb b/app/views/transactions/index.html.erb
index 671710c06..c56aec7a4 100644
--- a/app/views/transactions/index.html.erb
+++ b/app/views/transactions/index.html.erb
@@ -11,6 +11,9 @@
           <% menu.with_item(variant: "link", text: "Edit merchants", href: family_merchants_path, icon: "store", data: { turbo_frame: :_top }) %>
           <% menu.with_item(variant: "link", text: "Edit imports", href: imports_path, icon: "hard-drive-upload", data: { turbo_frame: :_top }) %>
           <% menu.with_item(variant: "link", text: "Import", href: new_import_path, icon: "download", data: { turbo_frame: "modal", class_name: "md:!hidden" }) %>
+          <% if @uncategorized_count > 0 %>
+            <% menu.with_item(variant: "link", text: t(".categorize_button", count: @uncategorized_count), href: transactions_categorize_path, icon: "tag", data: { turbo_frame: :_top }) %>
+          <% end %>
         <% end %>
 
         <div class="hidden md:flex">
diff --git a/config/locales/breadcrumbs/en.yml b/config/locales/breadcrumbs/en.yml
index 9d81ba325..1c840acdc 100644
--- a/config/locales/breadcrumbs/en.yml
+++ b/config/locales/breadcrumbs/en.yml
@@ -1,6 +1,8 @@
 ---
 en:
   breadcrumbs:
+    categorize: Categorize
     exports: Exports
     home: Home
     imports: Imports
+    transactions: Transactions
diff --git a/config/locales/views/transactions/en.yml b/config/locales/views/transactions/en.yml
index 78a8e5305..c5b5c3f0c 100644
--- a/config/locales/views/transactions/en.yml
+++ b/config/locales/views/transactions/en.yml
@@ -124,6 +124,42 @@ en:
       transaction: transaction
       transactions: transactions
       import: Import
+      categorize_button:
+        one: "Categorize (1)"
+        other: "Categorize (%{count})"
+    categorizes:
+      show:
+        exit: "Exit"
+        skip: "Skip"
+        remaining:
+          one: "1 uncategorized transaction remaining"
+          other: "%{count} uncategorized transactions remaining"
+        transaction_count:
+          one: "1 transaction"
+          other: "%{count} transactions"
+        transactions_hint: "Uncheck to exclude a transaction, or assign it a different category directly in its row."
+        assign_category: "Assign a category"
+        assign_category_prompt: "→ assign"
+        filter_placeholder: "Search categories..."
+        col_transaction: "Transaction"
+        col_date: "Date"
+        col_amount: "Amount"
+        col_category: "Category"
+        type_income: "Income"
+        type_expense: "Expense"
+        create_rule_label: "Create Categorization Rule"
+        rule_description_prefix: "Future %{type} transactions with name containing"
+        rule_description_suffix: "should also get this category."
+        no_categories: "No matching categories"
+        all_done: "All transactions are categorized"
+      create:
+        categorized:
+          one: "1 transaction categorized"
+          other: "%{count} transactions categorized"
+        rule_creation_failed: "Transactions categorized, but the rule could not be created (it may already exist)."
+      entry_row:
+        include_checkbox: "Include %{name}"
+        assign_category_select: "Assign category for %{name}"
     list:
       drag_drop_title: Drop CSV to import
       drag_drop_subtitle: Upload transactions directly
diff --git a/config/routes.rb b/config/routes.rb
index 4aa815976..98895fa3c 100644
--- a/config/routes.rb
+++ b/config/routes.rb
@@ -274,6 +274,10 @@ Rails.application.routes.draw do
   namespace :transactions do
     resource :bulk_deletion, only: :create
     resource :bulk_update, only: %i[new create]
+    resource :categorize, only: %i[show create] do
+      patch :assign_entry, on: :collection
+      get :preview_rule, on: :collection
+    end
   end
 
   resources :transactions, only: %i[index new create show update destroy] do
diff --git a/db/schema.rb b/db/schema.rb
index 4a082ca1d..90ff71313 100644
--- a/db/schema.rb
+++ b/db/schema.rb
@@ -63,8 +63,6 @@ ActiveRecord::Schema[7.2].define(version: 2026_03_28_120000) do
     t.string "institution_name"
     t.string "institution_domain"
     t.text "notes"
-    t.jsonb "holdings_snapshot_data"
-    t.datetime "holdings_snapshot_at"
     t.uuid "owner_id"
     t.index ["accountable_id", "accountable_type"], name: "index_accounts_on_accountable_id_and_accountable_type"
     t.index ["accountable_type"], name: "index_accounts_on_accountable_type"
@@ -1184,7 +1182,7 @@ ActiveRecord::Schema[7.2].define(version: 2026_03_28_120000) do
     t.index ["country_code"], name: "index_securities_on_country_code"
     t.index ["exchange_operating_mic"], name: "index_securities_on_exchange_operating_mic"
     t.index ["kind"], name: "index_securities_on_kind"
-    t.check_constraint "kind = ANY (ARRAY['standard'::text, 'cash'::text])", name: "chk_securities_kind"
+    t.check_constraint "kind::text = ANY (ARRAY['standard'::character varying, 'cash'::character varying]::text[])", name: "chk_securities_kind"
   end
 
   create_table "security_prices", id: :uuid, default: -> { "gen_random_uuid()" }, force: :cascade do |t|
@@ -1514,10 +1512,6 @@ ActiveRecord::Schema[7.2].define(version: 2026_03_28_120000) do
     t.string "kind", default: "reconciliation", null: false
   end
 
-# Could not dump table "vector_store_chunks" because of following StandardError
-#   Unknown type 'vector(768)' for column 'embedding'
-
-
   create_table "vehicles", id: :uuid, default: -> { "gen_random_uuid()" }, force: :cascade do |t|
     t.datetime "created_at", null: false
     t.datetime "updated_at", null: false
diff --git a/test/controllers/transactions/categorizes_controller_test.rb b/test/controllers/transactions/categorizes_controller_test.rb
new file mode 100644
index 000000000..a3628543e
--- /dev/null
+++ b/test/controllers/transactions/categorizes_controller_test.rb
@@ -0,0 +1,268 @@
+require "test_helper"
+
+class Transactions::CategorizesControllerTest < ActionDispatch::IntegrationTest
+  include EntriesTestHelper
+
+  setup do
+    sign_in @user = users(:family_admin)
+    @family = @user.family
+    @account = accounts(:depository)
+    @category = categories(:food_and_drink)
+    # Clear entries for isolation
+    @family.accounts.each { |a| a.entries.delete_all }
+  end
+
+  # GET /transactions/categorize
+
+  test "show redirects with notice when nothing to categorize" do
+    get transactions_categorize_url
+    assert_redirected_to transactions_url
+    assert_match "categorized", flash[:notice]
+  end
+
+  test "show renders wizard when uncategorized transactions exist" do
+    create_transaction(account: @account, name: "Starbucks")
+    get transactions_categorize_url
+    assert_response :success
+  end
+
+  test "show renders the first group at position 0" do
+    2.times { create_transaction(account: @account, name: "Netflix") }
+    3.times { create_transaction(account: @account, name: "Starbucks") }
+
+    get transactions_categorize_url(position: 0)
+
+    assert_response :success
+    assert_select "h2", text: "Starbucks"
+  end
+
+  test "show at position 1 skips first group" do
+    3.times { create_transaction(account: @account, name: "Starbucks") }
+    2.times { create_transaction(account: @account, name: "Netflix") }
+
+    get transactions_categorize_url(position: 1)
+
+    assert_response :success
+    assert_select "h2", text: "Netflix"
+  end
+
+  test "show redirects when position exceeds available groups" do
+    create_transaction(account: @account, name: "Starbucks")
+
+    get transactions_categorize_url(position: 99)
+
+    assert_redirected_to transactions_url
+  end
+
+  test "requires authentication" do
+    sign_out
+    get transactions_categorize_url
+    assert_redirected_to new_session_url
+  end
+
+  # Account sharing authorization
+
+  test "show only groups entries from accounts accessible to the user" do
+    accessible_account = accounts(:depository)       # shared with family_member (full_control)
+    inaccessible_account = accounts(:investment)     # not shared with family_member
+
+    create_transaction(account: accessible_account, name: "Starbucks")
+    create_transaction(account: inaccessible_account, name: "Starbucks")
+
+    sign_in users(:family_member)
+    get transactions_categorize_url(position: 0)
+
+    assert_response :success
+    # Only 1 entry should appear in the group — the inaccessible account's entry is hidden
+    assert_select "input[name='entry_ids[]']", count: 1
+  end
+
+  test "create does not categorize entries from inaccessible accounts" do
+    inaccessible_account = accounts(:investment)     # not shared with family_member
+    entry = create_transaction(account: inaccessible_account, name: "Starbucks")
+
+    sign_in users(:family_member)
+    post transactions_categorize_url,
+      params: {
+        position: 0,
+        grouping_key: "Starbucks",
+        entry_ids: [ entry.id ],
+        all_entry_ids: [ entry.id ],
+        category_id: @category.id
+      },
+      headers: { "Accept" => "text/vnd.turbo-stream.html" }
+
+    assert_nil entry.transaction.reload.category
+  end
+
+  test "assign_entry does not categorize an entry from an inaccessible account" do
+    inaccessible_account = accounts(:investment)     # not shared with family_member
+    entry = create_transaction(account: inaccessible_account, name: "Starbucks")
+
+    sign_in users(:family_member)
+    patch assign_entry_transactions_categorize_url, params: {
+      entry_id: entry.id,
+      category_id: @category.id,
+      position: 0,
+      all_entry_ids: [ entry.id ]
+    }
+
+    assert_response :not_found
+    assert_nil entry.transaction.reload.category
+  end
+
+  # GET /transactions/categorize/preview_rule
+
+  test "preview_rule returns matching entries for a filter" do
+    create_transaction(account: @account, name: "Amazon Prime")
+    create_transaction(account: @account, name: "Amazon Music")
+    create_transaction(account: @account, name: "Starbucks")
+
+    get preview_rule_transactions_categorize_url(filter: "Amazon"),
+      headers: { "Accept" => "text/vnd.turbo-stream.html" }
+
+    assert_response :success
+    assert_includes response.body, "Amazon Prime"
+    assert_includes response.body, "Amazon Music"
+    assert_not_includes response.body, "Starbucks"
+  end
+
+  test "preview_rule returns empty list for blank filter" do
+    create_transaction(account: @account, name: "Amazon")
+
+    get preview_rule_transactions_categorize_url(filter: ""),
+      headers: { "Accept" => "text/vnd.turbo-stream.html" }
+
+    assert_response :success
+    assert_not_includes response.body, "Amazon"
+  end
+
+  test "preview_rule requires authentication" do
+    sign_out
+    get preview_rule_transactions_categorize_url(filter: "Amazon")
+    assert_redirected_to new_session_url
+  end
+
+  private
+
+    def sign_out
+      @user.sessions.each { |s| delete session_path(s) }
+    end
+
+    # POST /transactions/categorize
+
+    test "create categorizes selected entries and returns redirect stream when all assigned" do
+      entry = create_transaction(account: @account, name: "Starbucks")
+
+      post transactions_categorize_url,
+        params: {
+          position: 0,
+          grouping_key: "Starbucks",
+          entry_ids: [ entry.id ],
+          all_entry_ids: [ entry.id ],
+          category_id: @category.id
+        },
+        headers: { "Accept" => "text/vnd.turbo-stream.html" }
+
+      assert_response :success
+      assert_equal @category, entry.transaction.reload.category
+      assert_includes response.body, "action=\"redirect\""
+    end
+
+    test "create removes assigned rows and replaces remaining when partial assignment" do
+      entry1 = create_transaction(account: @account, name: "Starbucks")
+      entry2 = create_transaction(account: @account, name: "Starbucks")
+
+      post transactions_categorize_url,
+        params: {
+          position: 0,
+          grouping_key: "Starbucks",
+          entry_ids: [ entry1.id ],
+          all_entry_ids: [ entry1.id, entry2.id ],
+          category_id: @category.id
+        },
+        headers: { "Accept" => "text/vnd.turbo-stream.html" }
+
+      assert_response :success
+      assert_equal @category, entry1.transaction.reload.category
+      assert_nil entry2.transaction.reload.category
+      # Remove stream for categorized entry
+      assert_includes response.body, "categorize_entry_#{entry1.id}"
+      # Replace stream for remaining entry (re-checked)
+      assert_includes response.body, "categorize_entry_#{entry2.id}"
+      # No redirect stream — still in the group
+      assert_not_includes response.body, "action=\"redirect\""
+    end
+
+    test "create with create_rule param creates rule with name and type conditions" do
+      entry = create_transaction(account: @account, name: "Netflix", amount: 15)
+
+      assert_difference "@family.rules.count", 1 do
+        post transactions_categorize_url,
+          params: {
+            position: 0,
+            grouping_key: "Netflix",
+            transaction_type: "expense",
+            entry_ids: [ entry.id ],
+            all_entry_ids: [ entry.id ],
+            category_id: @category.id,
+            create_rule: "1"
+          },
+          headers: { "Accept" => "text/vnd.turbo-stream.html" }
+      end
+
+      rule = @family.rules.find_by(name: "Netflix")
+      assert_not_nil rule
+      assert rule.active
+      assert rule.conditions.any? { |c| c.condition_type == "transaction_name" && c.value == "Netflix" }
+      assert rule.conditions.any? { |c| c.condition_type == "transaction_type" && c.value == "expense" }
+    end
+
+    test "create falls back to html redirect without turbo stream header" do
+      entry = create_transaction(account: @account, name: "Starbucks")
+
+      post transactions_categorize_url, params: {
+        position: 0,
+        grouping_key: "Starbucks",
+        entry_ids: [ entry.id ],
+        all_entry_ids: [ entry.id ],
+        category_id: @category.id
+      }
+
+      assert_redirected_to transactions_categorize_url(position: 0)
+      assert flash[:notice].present?
+    end
+
+    # PATCH /transactions/categorize/assign_entry
+
+    test "assign_entry categorizes single entry and returns remove stream" do
+      entry = create_transaction(account: @account, name: "Starbucks")
+      other = create_transaction(account: @account, name: "Starbucks")
+
+      patch assign_entry_transactions_categorize_url, params: {
+        entry_id: entry.id,
+        category_id: @category.id,
+        position: 0,
+        all_entry_ids: [ entry.id, other.id ]
+      }
+
+      assert_response :success
+      assert_equal @category, entry.transaction.reload.category
+      assert_includes response.body, "categorize_entry_#{entry.id}"
+      assert_not_includes response.body, "action=\"redirect\""
+    end
+
+    test "assign_entry returns redirect stream when last entry in group" do
+      entry = create_transaction(account: @account, name: "Starbucks")
+
+      patch assign_entry_transactions_categorize_url, params: {
+        entry_id: entry.id,
+        category_id: @category.id,
+        position: 0,
+        all_entry_ids: [ entry.id ]
+      }
+
+      assert_response :success
+      assert_includes response.body, "action=\"redirect\""
+    end
+end
diff --git a/test/models/transaction/grouper/by_merchant_or_name_test.rb b/test/models/transaction/grouper/by_merchant_or_name_test.rb
new file mode 100644
index 000000000..adb6320fa
--- /dev/null
+++ b/test/models/transaction/grouper/by_merchant_or_name_test.rb
@@ -0,0 +1,140 @@
+require "test_helper"
+
+class Transaction::Grouper::ByMerchantOrNameTest < ActiveSupport::TestCase
+  include EntriesTestHelper
+
+  setup do
+    @family = families(:dylan_family)
+    @account = accounts(:depository)
+    # Clear existing entries for isolation
+    @family.accounts.each { |a| a.entries.delete_all }
+  end
+
+  test "groups uncategorized transactions by merchant name when merchant present" do
+    merchant = merchants(:netflix)
+    create_transaction(account: @account, name: "NETFLIX.COM", merchant: merchant)
+    create_transaction(account: @account, name: "Netflix Monthly", merchant: merchant)
+
+    groups = Transaction::Grouper::ByMerchantOrName.call(@family.entries)
+
+    assert_equal 1, groups.size
+    assert_equal "Netflix", groups.first.grouping_key
+    assert_equal 2, groups.first.entries.size
+  end
+
+  test "falls back to entry name when no merchant" do
+    create_transaction(account: @account, name: "AMZN MKTP US")
+    create_transaction(account: @account, name: "AMZN MKTP US")
+
+    groups = Transaction::Grouper::ByMerchantOrName.call(@family.entries)
+
+    assert_equal 1, groups.size
+    assert_equal "AMZN MKTP US", groups.first.grouping_key
+    assert_equal 2, groups.first.entries.size
+  end
+
+  test "creates separate groups for different names" do
+    create_transaction(account: @account, name: "Starbucks")
+    create_transaction(account: @account, name: "Netflix")
+
+    groups = Transaction::Grouper::ByMerchantOrName.call(@family.entries)
+
+    assert_equal 2, groups.size
+  end
+
+  test "creates separate groups for same name with different types" do
+    create_transaction(account: @account, name: "Refund", amount: 50)   # expense
+    create_transaction(account: @account, name: "Refund", amount: -50)  # income
+
+    groups = Transaction::Grouper::ByMerchantOrName.call(@family.entries)
+
+    assert_equal 2, groups.size
+    types = groups.map(&:transaction_type).sort
+    assert_equal %w[expense income], types
+  end
+
+  test "sets transaction_type to income for negative amounts" do
+    create_transaction(account: @account, name: "Paycheck", amount: -1000)
+
+    groups = Transaction::Grouper::ByMerchantOrName.call(@family.entries)
+
+    assert_equal "income", groups.first.transaction_type
+  end
+
+  test "sets transaction_type to expense for positive amounts" do
+    create_transaction(account: @account, name: "Coffee", amount: 5)
+
+    groups = Transaction::Grouper::ByMerchantOrName.call(@family.entries)
+
+    assert_equal "expense", groups.first.transaction_type
+  end
+
+  test "excludes transfer kinds" do
+    create_transaction(account: @account, name: "CC Payment", kind: "cc_payment")
+    create_transaction(account: @account, name: "Funds Move", kind: "funds_movement")
+    create_transaction(account: @account, name: "Regular")
+
+    groups = Transaction::Grouper::ByMerchantOrName.call(@family.entries)
+
+    assert_equal 1, groups.size
+    assert_equal "Regular", groups.first.grouping_key
+  end
+
+  test "excludes already-categorized transactions" do
+    create_transaction(account: @account, name: "Categorized", category: categories(:food_and_drink))
+    create_transaction(account: @account, name: "Uncategorized")
+
+    groups = Transaction::Grouper::ByMerchantOrName.call(@family.entries)
+
+    assert_equal 1, groups.size
+    assert_equal "Uncategorized", groups.first.grouping_key
+  end
+
+  test "excludes excluded entries" do
+    entry = create_transaction(account: @account, name: "Excluded")
+    entry.update!(excluded: true)
+    create_transaction(account: @account, name: "Visible")
+
+    groups = Transaction::Grouper::ByMerchantOrName.call(@family.entries)
+
+    assert_equal 1, groups.size
+    assert_equal "Visible", groups.first.grouping_key
+  end
+
+  test "returns empty array when all transactions are categorized" do
+    create_transaction(account: @account, name: "Coffee", category: categories(:food_and_drink))
+
+    groups = Transaction::Grouper::ByMerchantOrName.call(@family.entries)
+
+    assert_empty groups
+  end
+
+  test "sorts groups by count descending then name ascending" do
+    3.times { create_transaction(account: @account, name: "Starbucks") }
+    create_transaction(account: @account, name: "Netflix")
+
+    groups = Transaction::Grouper::ByMerchantOrName.call(@family.entries)
+
+    assert_equal "Starbucks", groups.first.grouping_key
+    assert_equal "Netflix", groups.last.grouping_key
+  end
+
+  test "respects limit and offset" do
+    create_transaction(account: @account, name: "A")
+    create_transaction(account: @account, name: "B")
+    create_transaction(account: @account, name: "C")
+
+    # limit
+    groups = Transaction::Grouper::ByMerchantOrName.call(@family.entries, limit: 2)
+    assert_equal 2, groups.size
+
+    # all groups
+    all_groups = Transaction::Grouper::ByMerchantOrName.call(@family.entries, limit: 10)
+    assert_equal 3, all_groups.size
+
+    # offset skips leading groups
+    offset_groups = Transaction::Grouper::ByMerchantOrName.call(@family.entries, limit: 10, offset: 1)
+    assert_equal 2, offset_groups.size
+    assert_not_includes offset_groups.map(&:grouping_key), all_groups.first.grouping_key
+  end
+end