diff --git a/app/controllers/accounts_controller.rb b/app/controllers/accounts_controller.rb
index 1524b25d0..b71318b62 100644
--- a/app/controllers/accounts_controller.rb
+++ b/app/controllers/accounts_controller.rb
@@ -36,7 +36,7 @@ class AccountsController < ApplicationController
     @chart_view = params[:chart_view] || "balance"
     @tab = params[:tab]
     @q = params.fetch(:q, {}).permit(:search, status: [])
-    entries = @account.entries.search(@q).reverse_chronological
+    entries = @account.entries.where(excluded: false).search(@q).reverse_chronological
 
     @pagy, @entries = pagy(entries, limit: params[:per_page] || "10")
 
diff --git a/app/controllers/reports_controller.rb b/app/controllers/reports_controller.rb
index 91593f801..9a076701d 100644
--- a/app/controllers/reports_controller.rb
+++ b/app/controllers/reports_controller.rb
@@ -123,6 +123,9 @@ class ReportsController < ApplicationController
       # Investment metrics
       @investment_metrics = build_investment_metrics
 
+      # Investment flows (contributions/withdrawals)
+      @investment_flows = InvestmentFlowStatement.new(Current.family).period_totals(period: @period)
+
       # Flags for view rendering
       @has_accounts = Current.family.accounts.any?
     end
@@ -161,6 +164,14 @@ class ReportsController < ApplicationController
           visible: @investment_metrics[:has_investments],
           collapsible: true
         },
+        {
+          key: "investment_flows",
+          title: "reports.investment_flows.title",
+          partial: "reports/investment_flows",
+          locals: { investment_flows: @investment_flows },
+          visible: @investment_metrics[:has_investments] && (@investment_flows.contributions.amount > 0 || @investment_flows.withdrawals.amount > 0),
+          collapsible: true
+        },
         {
           key: "transactions_breakdown",
           title: "reports.transactions_breakdown.title",
@@ -345,14 +356,6 @@ class ReportsController < ApplicationController
       # Apply filters
       transactions = apply_transaction_filters(transactions)
 
-      # Get trades in the period (matching income_statement logic)
-      trades = Trade
-        .joins(:entry)
-        .joins(entry: :account)
-        .where(accounts: { family_id: Current.family.id, status: [ "draft", "active" ] })
-        .where(entries: { entryable_type: "Trade", excluded: false, date: @period.date_range })
-        .includes(entry: :account, category: [])
-
       # Get sort parameters
       sort_by = params[:sort_by] || "amount"
       sort_direction = params[:sort_direction] || "desc"
@@ -378,24 +381,6 @@ class ReportsController < ApplicationController
         grouped_data[key][:total] += converted_amount
       end
 
-      # Process trades
-      trades.each do |trade|
-        entry = trade.entry
-        is_expense = entry.amount > 0
-        type = is_expense ? "expense" : "income"
-        # Use "Other Investments" for trades without category
-        category_name = trade.category&.name || Category.other_investments_name
-        category_color = trade.category&.color || Category::OTHER_INVESTMENTS_COLOR
-
-        # Convert to family currency
-        converted_amount = Money.new(entry.amount.abs, entry.currency).exchange_to(family_currency, fallback_rate: 1).amount
-
-        key = [ category_name, type, category_color ]
-        grouped_data[key] ||= { total: 0, count: 0 }
-        grouped_data[key][:count] += 1
-        grouped_data[key][:total] += converted_amount
-      end
-
       # Convert to array
       result = grouped_data.map do |key, data|
         {
@@ -562,14 +547,6 @@ class ReportsController < ApplicationController
 
       transactions = apply_transaction_filters(transactions)
 
-      # Get trades in the period (matching income_statement logic)
-      trades = Trade
-        .joins(:entry)
-        .joins(entry: :account)
-        .where(accounts: { family_id: Current.family.id, status: [ "draft", "active" ] })
-        .where(entries: { entryable_type: "Trade", excluded: false, date: @period.date_range })
-        .includes(entry: :account, category: [])
-
       # Group by category, type, and month
       breakdown = {}
       family_currency = Current.family.currency
@@ -592,25 +569,6 @@ class ReportsController < ApplicationController
         breakdown[key][:total] += converted_amount
       end
 
-      # Process trades
-      trades.each do |trade|
-        entry = trade.entry
-        is_expense = entry.amount > 0
-        type = is_expense ? "expense" : "income"
-        # Use "Other Investments" for trades without category
-        category_name = trade.category&.name || Category.other_investments_name
-        month_key = entry.date.beginning_of_month
-
-        # Convert to family currency
-        converted_amount = Money.new(entry.amount.abs, entry.currency).exchange_to(family_currency, fallback_rate: 1).amount
-
-        key = [ category_name, type ]
-        breakdown[key] ||= { category: category_name, type: type, months: {}, total: 0 }
-        breakdown[key][:months][month_key] ||= 0
-        breakdown[key][:months][month_key] += converted_amount
-        breakdown[key][:total] += converted_amount
-      end
-
       # Convert to array and sort by type and total (descending)
       result = breakdown.map do |key, data|
         {
diff --git a/app/controllers/trades_controller.rb b/app/controllers/trades_controller.rb
index 46cd1f39a..f131c47ef 100644
--- a/app/controllers/trades_controller.rb
+++ b/app/controllers/trades_controller.rb
@@ -55,7 +55,7 @@ class TradesController < ApplicationController
     def entry_params
       params.require(:entry).permit(
         :name, :date, :amount, :currency, :excluded, :notes, :nature,
-        entryable_attributes: [ :id, :qty, :price, :category_id ]
+        entryable_attributes: [ :id, :qty, :price, :investment_activity_label ]
       )
     end
 
@@ -73,11 +73,27 @@ class TradesController < ApplicationController
 
       qty = update_params[:entryable_attributes][:qty]
       price = update_params[:entryable_attributes][:price]
+      nature = update_params[:nature]
 
       if qty.present? && price.present?
-        qty = update_params[:nature] == "inflow" ? -qty.to_d : qty.to_d
+        is_sell = nature == "inflow"
+        qty = is_sell ? -qty.to_d.abs : qty.to_d.abs
         update_params[:entryable_attributes][:qty] = qty
         update_params[:amount] = qty * price.to_d
+
+        # Sync investment_activity_label with Buy/Sell type if not explicitly set to something else
+        # Check both the submitted param and the existing record's label
+        current_label = update_params[:entryable_attributes][:investment_activity_label].presence ||
+                        @entry.trade&.investment_activity_label
+        if current_label.blank? || current_label == "Buy" || current_label == "Sell"
+          update_params[:entryable_attributes][:investment_activity_label] = is_sell ? "Sell" : "Buy"
+        end
+
+        # Update entry name to reflect Buy/Sell change
+        ticker = @entry.trade&.security&.ticker
+        if ticker.present?
+          update_params[:name] = Trade.build_name(is_sell ? "sell" : "buy", qty.abs, ticker)
+        end
       end
 
       update_params.except(:nature)
diff --git a/app/controllers/transactions_controller.rb b/app/controllers/transactions_controller.rb
index 58220bd99..8c8ef6a21 100644
--- a/app/controllers/transactions_controller.rb
+++ b/app/controllers/transactions_controller.rb
@@ -149,6 +149,87 @@ class TransactionsController < ApplicationController
     redirect_back_or_to transactions_path
   end
 
+  def convert_to_trade
+    @transaction = Current.family.transactions.includes(entry: :account).find(params[:id])
+    @entry = @transaction.entry
+
+    unless @entry.account.investment?
+      flash[:alert] = t("transactions.convert_to_trade.errors.not_investment_account")
+      redirect_back_or_to transactions_path
+      return
+    end
+
+    render :convert_to_trade
+  end
+
+  def create_trade_from_transaction
+    @transaction = Current.family.transactions.includes(entry: :account).find(params[:id])
+    @entry = @transaction.entry
+
+    # Pre-transaction validations
+    unless @entry.account.investment?
+      flash[:alert] = t("transactions.convert_to_trade.errors.not_investment_account")
+      redirect_back_or_to transactions_path
+      return
+    end
+
+    if @entry.excluded?
+      flash[:alert] = t("transactions.convert_to_trade.errors.already_converted")
+      redirect_back_or_to transactions_path
+      return
+    end
+
+    # Resolve security before transaction
+    security = resolve_security_for_conversion
+    return if performed? # Early exit if redirect already happened
+
+    # Validate and calculate qty/price before transaction
+    qty, price = calculate_qty_and_price
+    return if performed? # Early exit if redirect already happened
+
+    activity_label = params[:investment_activity_label].presence
+    # Infer sell from amount sign: negative amount = money coming in = sell
+    is_sell = activity_label == "Sell" || (activity_label.blank? && @entry.amount < 0)
+
+    ActiveRecord::Base.transaction do
+      # For trades: positive qty = buy (money out), negative qty = sell (money in)
+      signed_qty = is_sell ? -qty : qty
+      trade_amount = qty * price
+      # Sells bring money in (negative amount), Buys take money out (positive amount)
+      signed_amount = is_sell ? -trade_amount : trade_amount
+
+      # Default activity label if not provided
+      activity_label ||= is_sell ? "Sell" : "Buy"
+
+      # Create trade entry
+      @entry.account.entries.create!(
+        name: params[:trade_name] || Trade.build_name(is_sell ? "sell" : "buy", qty, security.ticker),
+        date: @entry.date,
+        amount: signed_amount,
+        currency: @entry.currency,
+        entryable: Trade.new(
+          security: security,
+          qty: signed_qty,
+          price: price,
+          currency: @entry.currency,
+          investment_activity_label: activity_label
+        )
+      )
+
+      # Mark original transaction as excluded (soft delete)
+      @entry.update!(excluded: true)
+    end
+
+    flash[:notice] = t("transactions.convert_to_trade.success")
+    redirect_to account_path(@entry.account), status: :see_other
+  rescue ActiveRecord::RecordInvalid, ActiveRecord::RecordNotSaved => e
+    flash[:alert] = t("transactions.convert_to_trade.errors.conversion_failed", error: e.message)
+    redirect_back_or_to transactions_path, status: :see_other
+  rescue StandardError => e
+    flash[:alert] = t("transactions.convert_to_trade.errors.unexpected_error", error: e.message)
+    redirect_back_or_to transactions_path, status: :see_other
+  end
+
   def mark_as_recurring
     transaction = Current.family.transactions.includes(entry: :account).find(params[:id])
 
@@ -280,4 +361,64 @@ class TransactionsController < ApplicationController
     def preferences_params
       params.require(:preferences).permit(collapsed_sections: {})
     end
+
+    # Helper methods for convert_to_trade
+
+    def resolve_security_for_conversion
+      if params[:security_id] == "__custom__"
+        ticker = params[:custom_ticker].presence
+        unless ticker.present?
+          flash[:alert] = t("transactions.convert_to_trade.errors.enter_ticker")
+          redirect_back_or_to transactions_path
+          return nil
+        end
+
+        Security::Resolver.new(
+          ticker.strip,
+          exchange_operating_mic: params[:exchange_operating_mic].presence
+        ).resolve
+      elsif params[:security_id].present?
+        found = Security.find_by(id: params[:security_id])
+        unless found
+          flash[:alert] = t("transactions.convert_to_trade.errors.security_not_found")
+          redirect_back_or_to transactions_path
+          return nil
+        end
+        found
+      elsif params[:ticker].present?
+        Security::Resolver.new(
+          params[:ticker].strip,
+          exchange_operating_mic: params[:exchange_operating_mic].presence
+        ).resolve
+      end.tap do |security|
+        if security.nil? && !performed?
+          flash[:alert] = t("transactions.convert_to_trade.errors.select_security")
+          redirect_back_or_to transactions_path
+        end
+      end
+    end
+
+    def calculate_qty_and_price
+      amount = @entry.amount.abs
+      qty = params[:qty].present? ? params[:qty].to_d.abs : nil
+      price = params[:price].present? ? params[:price].to_d : nil
+
+      if qty.nil? && price.nil?
+        flash[:alert] = t("transactions.convert_to_trade.errors.enter_qty_or_price")
+        redirect_back_or_to transactions_path, status: :see_other
+        return [ nil, nil ]
+      elsif qty.nil? && price.present? && price > 0
+        qty = (amount / price).round(6)
+      elsif price.nil? && qty.present? && qty > 0
+        price = (amount / qty).round(4)
+      end
+
+      if qty.nil? || qty <= 0 || price.nil? || price <= 0
+        flash[:alert] = t("transactions.convert_to_trade.errors.invalid_qty_or_price")
+        redirect_back_or_to transactions_path, status: :see_other
+        return [ nil, nil ]
+      end
+
+      [ qty, price ]
+    end
 end
diff --git a/app/javascript/controllers/activity_label_quick_edit_controller.js b/app/javascript/controllers/activity_label_quick_edit_controller.js
new file mode 100644
index 000000000..ee10fdf2c
--- /dev/null
+++ b/app/javascript/controllers/activity_label_quick_edit_controller.js
@@ -0,0 +1,108 @@
+import { Controller } from "@hotwired/stimulus"
+
+export default class extends Controller {
+  static targets = ["dropdown", "badge"]
+  static values = {
+    url: String,
+    entryableId: String,
+    currentLabel: String,
+    entryableType: String,
+    convertUrl: String
+  }
+
+  connect() {
+    // Close dropdown when clicking outside
+    this.boundCloseOnClickOutside = this.closeOnClickOutside.bind(this)
+    document.addEventListener("click", this.boundCloseOnClickOutside)
+  }
+
+  disconnect() {
+    document.removeEventListener("click", this.boundCloseOnClickOutside)
+  }
+
+  toggle(event) {
+    event.preventDefault()
+    event.stopPropagation()
+
+    if (this.hasDropdownTarget) {
+      this.dropdownTarget.classList.toggle("hidden")
+    }
+  }
+
+  closeOnClickOutside(event) {
+    if (!this.element.contains(event.target)) {
+      this.close()
+    }
+  }
+
+  close() {
+    if (this.hasDropdownTarget) {
+      this.dropdownTarget.classList.add("hidden")
+    }
+  }
+
+  async select(event) {
+    event.preventDefault()
+    event.stopPropagation()
+
+    const label = event.currentTarget.dataset.label
+
+    // Don't update if it's the same label
+    if (label === this.currentLabelValue) {
+      this.close()
+      return
+    }
+
+    // For Transactions: Buy/Sell should prompt to convert to trade
+    if (this.entryableTypeValue === "Transaction" && (label === "Buy" || label === "Sell") && this.hasConvertUrlValue) {
+      this.close()
+      // Navigate to convert-to-trade modal in a Turbo frame, passing the selected label
+      const url = new URL(this.convertUrlValue, window.location.origin)
+      url.searchParams.set("activity_label", label)
+      Turbo.visit(url.toString(), { frame: "modal" })
+      return
+    }
+
+    // For other labels (Dividend, Interest, Fee, etc.) or for Trades, just save the label
+    const csrfToken = document.querySelector('meta[name="csrf-token"]')?.content
+    if (!csrfToken) {
+      console.error("CSRF token not found")
+      return
+    }
+
+    try {
+      const response = await fetch(this.urlValue, {
+        method: "PATCH",
+        headers: {
+          "Content-Type": "application/json",
+          "X-CSRF-Token": csrfToken,
+          "Accept": "text/vnd.turbo-stream.html"
+        },
+        body: JSON.stringify({
+          entry: {
+            entryable_attributes: {
+              id: this.entryableIdValue,
+              investment_activity_label: label
+            }
+          }
+        })
+      })
+
+      if (response.ok) {
+        const contentType = response.headers.get("content-type")
+        if (contentType?.includes("text/vnd.turbo-stream.html")) {
+          // Let Turbo handle the stream response
+          const html = await response.text()
+          Turbo.renderStreamMessage(html)
+        }
+        // Update local state and badge
+        this.currentLabelValue = label
+        this.close()
+      } else {
+        console.error("Failed to update activity label:", response.status)
+      }
+    } catch (error) {
+      console.error("Error updating activity label:", error)
+    }
+  }
+}
diff --git a/app/javascript/controllers/convert_to_trade_controller.js b/app/javascript/controllers/convert_to_trade_controller.js
new file mode 100644
index 000000000..c0e71663b
--- /dev/null
+++ b/app/javascript/controllers/convert_to_trade_controller.js
@@ -0,0 +1,21 @@
+import { Controller } from "@hotwired/stimulus"
+
+export default class extends Controller {
+  static targets = ["customWrapper", "customField", "tickerSelect"]
+
+  toggleCustomTicker(event) {
+    const value = event.target.value
+
+    if (value === "__custom__") {
+      // Show custom ticker field
+      this.customWrapperTarget.classList.remove("hidden")
+      this.customFieldTarget.required = true
+      this.customFieldTarget.focus()
+    } else {
+      // Hide custom ticker field
+      this.customWrapperTarget.classList.add("hidden")
+      this.customFieldTarget.required = false
+      this.customFieldTarget.value = ""
+    }
+  }
+}
diff --git a/app/models/account/provider_import_adapter.rb b/app/models/account/provider_import_adapter.rb
index bae56389e..932edf57f 100644
--- a/app/models/account/provider_import_adapter.rb
+++ b/app/models/account/provider_import_adapter.rb
@@ -142,10 +142,28 @@ class Account::ProviderImportAdapter
         entry.transaction.save!
       end
 
-      # Set investment activity label if provided and not already set
-      if investment_activity_label.present? && entry.entryable.is_a?(Transaction)
-        if entry.transaction.investment_activity_label.blank?
-          entry.transaction.assign_attributes(investment_activity_label: investment_activity_label)
+      # Auto-detect investment activity labels for investment accounts
+      detected_label = investment_activity_label
+      if account.investment? && detected_label.nil? && entry.entryable.is_a?(Transaction)
+        detected_label = detect_activity_label(name, amount)
+      end
+
+      # Auto-set kind for internal movements and contributions
+      auto_kind = nil
+      if Transaction::INTERNAL_MOVEMENT_LABELS.include?(detected_label)
+        auto_kind = "funds_movement"
+      elsif detected_label == "Contribution"
+        auto_kind = "investment_contribution"
+      end
+
+      # Set investment activity label and kind if detected
+      if entry.entryable.is_a?(Transaction)
+        if detected_label.present? && entry.transaction.investment_activity_label.blank?
+          entry.transaction.assign_attributes(investment_activity_label: detected_label)
+        end
+
+        if auto_kind.present?
+          entry.transaction.assign_attributes(kind: auto_kind)
         end
       end
 
@@ -484,8 +502,9 @@ class Account::ProviderImportAdapter
   # @param name [String, nil] Optional custom name for the trade
   # @param external_id [String, nil] Provider's unique ID (optional, for deduplication)
   # @param source [String] Provider name
+  # @param activity_label [String, nil] Investment activity label (e.g., "Buy", "Sell", "Reinvestment")
   # @return [Entry] The created entry with trade
-  def import_trade(security:, quantity:, price:, amount:, currency:, date:, name: nil, external_id: nil, source:)
+  def import_trade(security:, quantity:, price:, amount:, currency:, date:, name: nil, external_id: nil, source:, activity_label: nil)
     raise ArgumentError, "security is required" if security.nil?
     raise ArgumentError, "source is required" if source.blank?
 
@@ -522,7 +541,8 @@ class Account::ProviderImportAdapter
         security: security,
         qty: quantity,
         price: price,
-        currency: currency
+        currency: currency,
+        investment_activity_label: activity_label || (quantity > 0 ? "Buy" : "Sell")
       )
 
       entry.assign_attributes(
@@ -790,6 +810,36 @@ class Account::ProviderImportAdapter
     )
   end
 
+  # Auto-detects investment activity label from transaction name and amount
+  # Only detects extremely obvious cases to maintain high accuracy
+  # Users can always manually adjust the label afterward
+  #
+  # @param name [String] Transaction name/description
+  # @param amount [BigDecimal, Numeric] Transaction amount (positive or negative)
+  # @return [String, nil] Detected activity label or nil if no pattern matches
+  def detect_activity_label(name, amount)
+    return nil if name.blank?
+
+    name_lower = name.downcase.strip
+
+    # Only detect the most obvious patterns - be conservative to avoid false positives
+    # Users can manually adjust labels for edge cases
+    case name_lower
+    when /^dividend\b/, /\bdividend payment\b/, /\bqualified dividend\b/, /\bordinary dividend\b/
+      "Dividend"
+    when /^interest\b/, /\binterest income\b/, /\binterest payment\b/
+      "Interest"
+    when /^fee\b/, /\bmanagement fee\b/, /\badvisory fee\b/, /\btransaction fee\b/
+      "Fee"
+    when /\bemployer match\b/, /\bemployer contribution\b/
+      "Contribution"
+    when /\b401[k\(]/, /\bira contribution\b/, /\broth contribution\b/
+      "Contribution"
+    else
+      nil # Let user categorize manually - default to nil for safety
+    end
+  end
+
   # Determines why an entry should be skipped during sync.
   # Returns nil if entry should NOT be skipped.
   #
diff --git a/app/models/category.rb b/app/models/category.rb
index f668ac1fc..b6586492e 100644
--- a/app/models/category.rb
+++ b/app/models/category.rb
@@ -1,6 +1,5 @@
 class Category < ApplicationRecord
   has_many :transactions, dependent: :nullify, class_name: "Transaction"
-  has_many :trades, dependent: :nullify
   has_many :import_mappings, as: :mappable, dependent: :destroy, class_name: "Import::Mapping"
 
   belongs_to :family
diff --git a/app/models/income_statement/totals.rb b/app/models/income_statement/totals.rb
index 758ae6be3..ffcb468b1 100644
--- a/app/models/income_statement/totals.rb
+++ b/app/models/income_statement/totals.rb
@@ -96,6 +96,10 @@ class IncomeStatement::Totals
           er.to_currency = :target_currency
         )
         WHERE at.kind NOT IN ('funds_movement', 'one_time', 'cc_payment', 'investment_contribution')
+          AND (
+            at.investment_activity_label IS NULL
+            OR at.investment_activity_label NOT IN ('Transfer', 'Sweep In', 'Sweep Out', 'Exchange')
+          )
           AND ae.excluded = false
                     AND a.family_id = :family_id
           AND a.status IN ('draft', 'active')
@@ -104,30 +108,14 @@ class IncomeStatement::Totals
     end
 
     def trades_subquery_sql
-      # Get trades for the same family and date range as transactions
-      # Trades without categories appear as "Uncategorized Investments" (separate from regular uncategorized)
+      # Trades are completely excluded from income/expense budgets
+      # Rationale: Trades represent portfolio rebalancing, not cash flow
+      # Example: Selling $10k AAPL to buy MSFT = no net worth change, not an expense
+      # Contributions/withdrawals are tracked separately as Transactions with activity labels
       <<~SQL
-        SELECT
-          c.id as category_id,
-          c.parent_id as parent_category_id,
-          CASE WHEN ae.amount < 0 THEN 'income' ELSE 'expense' END as classification,
-          ABS(SUM(ae.amount * COALESCE(er.rate, 1))) as total,
-          COUNT(ae.id) as entry_count,
-          CASE WHEN t.category_id IS NULL THEN true ELSE false END as is_uncategorized_investment
-        FROM trades t
-        JOIN entries ae ON ae.entryable_id = t.id AND ae.entryable_type = 'Trade'
-        JOIN accounts a ON a.id = ae.account_id
-        LEFT JOIN categories c ON c.id = t.category_id
-        LEFT JOIN exchange_rates er ON (
-          er.date = ae.date AND
-          er.from_currency = ae.currency AND
-          er.to_currency = :target_currency
-        )
-        WHERE a.family_id = :family_id
-          AND a.status IN ('draft', 'active')
-          AND ae.excluded = false
-                    AND ae.date BETWEEN :start_date AND :end_date
-        GROUP BY c.id, c.parent_id, CASE WHEN ae.amount < 0 THEN 'income' ELSE 'expense' END, CASE WHEN t.category_id IS NULL THEN true ELSE false END
+        SELECT NULL as category_id, NULL as parent_category_id, NULL as classification,
+               NULL as total, NULL as entry_count, NULL as is_uncategorized_investment
+        WHERE false
       SQL
     end
 
diff --git a/app/models/investment_flow_statement.rb b/app/models/investment_flow_statement.rb
new file mode 100644
index 000000000..d17a71266
--- /dev/null
+++ b/app/models/investment_flow_statement.rb
@@ -0,0 +1,30 @@
+class InvestmentFlowStatement
+  include Monetizable
+
+  attr_reader :family
+
+  def initialize(family)
+    @family = family
+  end
+
+  # Get contribution/withdrawal totals for a period
+  def period_totals(period: Period.current_month)
+    transactions = family.transactions
+      .visible
+      .excluding_pending
+      .where(entries: { date: period.date_range })
+      .where(kind: %w[standard investment_contribution])
+      .where(investment_activity_label: %w[Contribution Withdrawal])
+
+    contributions = transactions.where(investment_activity_label: "Contribution").sum("entries.amount").abs
+    withdrawals = transactions.where(investment_activity_label: "Withdrawal").sum("entries.amount").abs
+
+    PeriodTotals.new(
+      contributions: Money.new(contributions, family.currency),
+      withdrawals: Money.new(withdrawals, family.currency),
+      net_flow: Money.new(contributions - withdrawals, family.currency)
+    )
+  end
+
+  PeriodTotals = Data.define(:contributions, :withdrawals, :net_flow)
+end
diff --git a/app/models/plaid_account/investments/transactions_processor.rb b/app/models/plaid_account/investments/transactions_processor.rb
index d90657ce6..5cabccb2c 100644
--- a/app/models/plaid_account/investments/transactions_processor.rb
+++ b/app/models/plaid_account/investments/transactions_processor.rb
@@ -72,7 +72,8 @@ class PlaidAccount::Investments::TransactionsProcessor
         currency: transaction["iso_currency_code"],
         date: transaction["date"],
         name: transaction["name"],
-        source: "plaid"
+        source: "plaid",
+        activity_label: label_from_plaid_type(transaction)
       )
     end
 
diff --git a/app/models/trade.rb b/app/models/trade.rb
index b9233f9db..0692fae96 100644
--- a/app/models/trade.rb
+++ b/app/models/trade.rb
@@ -4,10 +4,13 @@ class Trade < ApplicationRecord
   monetize :price
 
   belongs_to :security
-  belongs_to :category, optional: true
+
+  # Use the same activity labels as Transaction
+  ACTIVITY_LABELS = Transaction::ACTIVITY_LABELS.dup.freeze
 
   validates :qty, presence: true
   validates :price, :currency, presence: true
+  validates :investment_activity_label, inclusion: { in: ACTIVITY_LABELS }, allow_nil: true
 
   # Trade types for categorization
   def buy?
@@ -35,4 +38,10 @@ class Trade < ApplicationRecord
 
     Trend.new(current: current_value, previous: cost_basis)
   end
+
+  # Trades are always excluded from expense budgets
+  # They represent portfolio management, not living expenses
+  def excluded_from_budget?
+    true
+  end
 end
diff --git a/app/models/trade/create_form.rb b/app/models/trade/create_form.rb
index a6973df72..d822131c5 100644
--- a/app/models/trade/create_form.rb
+++ b/app/models/trade/create_form.rb
@@ -42,7 +42,7 @@ class Trade::CreateForm
           price: price,
           currency: currency,
           security: security,
-          category: investment_category_for(type)
+          investment_activity_label: type.capitalize # "buy" → "Buy", "sell" → "Sell"
         )
       )
 
@@ -54,14 +54,6 @@ class Trade::CreateForm
       trade_entry
     end
 
-    def investment_category_for(trade_type)
-      # Buy trades are categorized as "Savings & Investments" (expense)
-      # Sell trades are left uncategorized for now
-      return nil unless trade_type == "buy"
-
-      account.family.categories.find_by(name: "Savings & Investments")
-    end
-
     def create_interest_income
       signed_amount = amount.to_d * -1
 
diff --git a/app/models/trade_import.rb b/app/models/trade_import.rb
index ed0f17bcd..e8372bed4 100644
--- a/app/models/trade_import.rb
+++ b/app/models/trade_import.rb
@@ -21,7 +21,7 @@ class TradeImport < Import
           qty: row.qty,
           currency: row.currency.presence || mapped_account.currency,
           price: row.price,
-          category: investment_category_for(row.qty, mapped_account.family),
+          investment_activity_label: investment_activity_label_for(row.qty),
           entry: Entry.new(
             account: mapped_account,
             date: row.date_iso,
@@ -78,12 +78,11 @@ class TradeImport < Import
   end
 
   private
-    def investment_category_for(qty, family)
-      # Buy trades (positive qty) are categorized as "Savings & Investments"
-      # Sell trades are left uncategorized - users will be prompted to categorize
-      return nil unless qty.to_d.positive?
-
-      family.categories.find_by(name: "Savings & Investments")
+    def investment_activity_label_for(qty)
+      # Set activity label based on quantity signage
+      # Buy trades have positive qty, Sell trades have negative qty
+      return nil if qty.blank? || qty.to_d.zero?
+      qty.to_d.positive? ? "Buy" : "Sell"
     end
 
     def find_or_create_security(ticker: nil, exchange_operating_mic: nil)
diff --git a/app/models/transaction.rb b/app/models/transaction.rb
index e1a86afb5..4850923b2 100644
--- a/app/models/transaction.rb
+++ b/app/models/transaction.rb
@@ -26,6 +26,9 @@ class Transaction < ApplicationRecord
     "Interest", "Fee", "Transfer", "Contribution", "Withdrawal", "Exchange", "Other"
   ].freeze
 
+  # Internal movement labels that should be excluded from budget (auto cash management)
+  INTERNAL_MOVEMENT_LABELS = [ "Transfer", "Sweep In", "Sweep Out", "Exchange" ].freeze
+
   # Pending transaction scopes - filter based on provider pending flags in extra JSONB
   # Works with any provider that stores pending status in extra["provider_name"]["pending"]
   scope :pending, -> {
diff --git a/app/views/investment_activity/_badge.html.erb b/app/views/investment_activity/_badge.html.erb
new file mode 100644
index 000000000..549d5b33f
--- /dev/null
+++ b/app/views/investment_activity/_badge.html.erb
@@ -0,0 +1,33 @@
+<%# locals: (label:) %>
+<%# Simple non-interactive badge for displaying activity labels %>
+<%
+  # Color mapping for different investment activity labels
+  color = case label
+  when "Buy"
+    "rgb(59 130 246)" # blue
+  when "Sell"
+    "rgb(239 68 68)" # red
+  when "Dividend", "Interest"
+    "rgb(34 197 94)" # green
+  when "Contribution"
+    "rgb(168 85 247)" # purple
+  when "Withdrawal"
+    "rgb(249 115 22)" # orange
+  when "Fee"
+    "rgb(107 114 128)" # gray
+  when "Transfer", "Sweep In", "Sweep Out", "Exchange"
+    "rgb(107 114 128)" # gray
+  when "Reinvestment"
+    "rgb(59 130 246)" # blue
+  else
+    "rgb(107 114 128)" # gray for "Other"
+  end
+%>
+
+<span class="inline-flex items-center gap-1 text-xs font-medium rounded px-1.5 py-0.5 border"
+      style="
+        background-color: color-mix(in oklab, <%= color %> 10%, transparent);
+        border-color: color-mix(in oklab, <%= color %> 20%, transparent);
+        color: <%= color %>;">
+  <%= label %>
+</span>
diff --git a/app/views/investment_activity/_quick_edit_badge.html.erb b/app/views/investment_activity/_quick_edit_badge.html.erb
new file mode 100644
index 000000000..4db357ef2
--- /dev/null
+++ b/app/views/investment_activity/_quick_edit_badge.html.erb
@@ -0,0 +1,95 @@
+<%# locals: (entry:, entryable:) %>
+<%
+  label = entryable.investment_activity_label
+  has_label = label.present?
+
+  # Build the correct URL based on entryable type
+  update_url = entryable.is_a?(Transaction) ? transaction_path(entry) : trade_path(entry)
+
+  # Color mapping for different investment activity labels using design system tokens
+  color = if has_label
+    case label
+    when "Buy"
+      "var(--color-blue-500)"
+    when "Sell"
+      "var(--color-red-500)"
+    when "Dividend", "Interest"
+      "var(--color-green-500)"
+    when "Contribution"
+      "var(--color-violet-500)"
+    when "Withdrawal"
+      "var(--color-orange-500)"
+    when "Fee"
+      "var(--color-gray-500)"
+    when "Transfer", "Sweep In", "Sweep Out", "Exchange"
+      "var(--color-gray-500)"
+    when "Reinvestment"
+      "var(--color-blue-500)"
+    else
+      "var(--color-gray-500)" # for "Other"
+    end
+  else
+    "var(--color-gray-400)" # slightly lighter for empty state
+  end
+
+  activity_labels = entryable.is_a?(Trade) ? Trade::ACTIVITY_LABELS : Transaction::ACTIVITY_LABELS
+  entryable_type = entryable.is_a?(Trade) ? "Trade" : "Transaction"
+  convert_url = entryable.is_a?(Transaction) ? convert_to_trade_transaction_path(entryable) : nil
+%>
+
+<div class="relative"
+     data-controller="activity-label-quick-edit"
+     data-activity-label-quick-edit-url-value="<%= update_url %>"
+     data-activity-label-quick-edit-entryable-id-value="<%= entryable.id %>"
+     data-activity-label-quick-edit-current-label-value="<%= label %>"
+     data-activity-label-quick-edit-entryable-type-value="<%= entryable_type %>"
+     <% if convert_url %>
+     data-activity-label-quick-edit-convert-url-value="<%= convert_url %>"
+     <% end %>>
+
+  <button type="button"
+          class="inline-flex items-center gap-1 text-xs font-medium rounded-full px-2.5 py-1 cursor-pointer hover:opacity-80 transition-opacity"
+          style="<% if has_label %>
+            background-color: color-mix(in oklab, <%= color %> 15%, transparent);
+            border: 1px solid color-mix(in oklab, <%= color %> 25%, transparent);
+            color: <%= color %>;
+          <% else %>
+            background-color: var(--color-surface-inset);
+            border: 1px solid var(--color-border-secondary);
+            color: var(--color-text-secondary);
+          <% end %>"
+          data-action="click->activity-label-quick-edit#toggle"
+          data-activity-label-quick-edit-target="badge"
+          title="<%= has_label ? t("transactions.transaction.activity_type_tooltip") : t("transactions.show.activity_type") %>">
+    <% if has_label %>
+      <%= label %>
+    <% else %>
+      <%= icon "tag", size: "xs", color: "current" %>
+      <span><%= t("transactions.show.activity_type") %></span>
+    <% end %>
+    <%= icon "chevron-down", size: "xs", color: "current" %>
+  </button>
+
+  <!-- Dropdown menu -->
+  <div class="hidden absolute right-0 z-50 mt-1 w-44 rounded-lg border border-primary bg-container shadow-lg"
+       data-activity-label-quick-edit-target="dropdown">
+    <div class="py-1 max-h-64 overflow-y-auto">
+      <% if has_label %>
+        <button type="button"
+                class="w-full text-left px-3 py-1.5 text-sm text-secondary hover:bg-surface-inset transition-colors border-b border-primary"
+                data-action="click->activity-label-quick-edit#select"
+                data-label="">
+          <span class="italic"><%= t("transactions.form.none") %></span>
+        </button>
+      <% end %>
+      <% activity_labels.each do |activity_label| %>
+        <button type="button"
+                class="w-full text-left px-3 py-1.5 text-sm text-primary hover:bg-surface-inset transition-colors <%= activity_label == label ? "font-semibold bg-surface-inset" : "" %>"
+                data-action="click->activity-label-quick-edit#select"
+                data-label="<%= activity_label %>">
+          <%= activity_label %>
+        </button>
+      <% end %>
+    </div>
+  </div>
+</div>
diff --git a/app/views/pages/dashboard/_investment_summary.html.erb b/app/views/pages/dashboard/_investment_summary.html.erb
index e35a5e443..30b83a067 100644
--- a/app/views/pages/dashboard/_investment_summary.html.erb
+++ b/app/views/pages/dashboard/_investment_summary.html.erb
@@ -77,21 +77,40 @@
 
     <%# Investment Activity Summary %>
     <% totals = investment_statement.totals(period: period) %>
-    <% if totals.trades_count > 0 %>
-      <div class="px-4 pt-2">
-        <p class="text-xs text-secondary uppercase font-medium mb-2"><%= t(".period_activity", period: period.label) %></p>
-        <div class="flex gap-4 text-sm">
-          <div>
-            <span class="text-secondary"><%= t(".contributions") %>:</span>
-            <span class="font-medium text-primary"><%= format_money(totals.contributions) %></span>
-          </div>
-          <div>
-            <span class="text-secondary"><%= t(".withdrawals") %>:</span>
-            <span class="font-medium text-primary"><%= format_money(totals.withdrawals) %></span>
-          </div>
-          <div>
-            <span class="text-secondary"><%= t(".trades") %>:</span>
-            <span class="font-medium text-primary"><%= totals.trades_count %></span>
+    <% if totals.trades_count > 0 || totals.contributions.to_f > 0 || totals.withdrawals.to_f > 0 %>
+      <div class="bg-container-inset rounded-xl p-1 mx-4">
+        <div class="px-4 py-2 flex items-center uppercase text-xs font-medium text-secondary">
+          <%= t(".period_activity", period: period.label) %>
+        </div>
+        <div class="shadow-border-xs rounded-lg bg-container font-medium text-sm">
+          <div class="p-4 flex items-center justify-between gap-4">
+            <div class="flex items-center gap-2">
+              <div class="w-8 h-8 rounded-full bg-green-500/10 flex items-center justify-center">
+                <%= icon "trending-up", size: "sm", color: "green" %>
+              </div>
+              <div>
+                <p class="text-xs text-secondary"><%= t(".contributions") %></p>
+                <p class="font-medium text-green-600"><%= format_money(totals.contributions) %></p>
+              </div>
+            </div>
+            <div class="flex items-center gap-2">
+              <div class="w-8 h-8 rounded-full bg-orange-500/10 flex items-center justify-center">
+                <%= icon "trending-down", size: "sm", color: "orange" %>
+              </div>
+              <div>
+                <p class="text-xs text-secondary"><%= t(".withdrawals") %></p>
+                <p class="font-medium text-orange-600"><%= format_money(totals.withdrawals) %></p>
+              </div>
+            </div>
+            <div class="flex items-center gap-2">
+              <div class="w-8 h-8 rounded-full bg-blue-500/10 flex items-center justify-center">
+                <%= icon "arrow-left-right", size: "sm", color: "blue" %>
+              </div>
+              <div>
+                <p class="text-xs text-secondary"><%= t(".trades") %></p>
+                <p class="font-medium text-primary"><%= totals.trades_count %></p>
+              </div>
+            </div>
           </div>
         </div>
       </div>
diff --git a/app/views/reports/_investment_flows.html.erb b/app/views/reports/_investment_flows.html.erb
new file mode 100644
index 000000000..99a01273a
--- /dev/null
+++ b/app/views/reports/_investment_flows.html.erb
@@ -0,0 +1,44 @@
+<%# locals: (investment_flows:) %>
+<div class="space-y-4">
+  <p class="text-sm text-secondary">
+    Track money flowing into and out of your investment accounts through contributions and withdrawals.
+  </p>
+
+  <div class="grid grid-cols-1 md:grid-cols-3 gap-4">
+    <!-- Contributions -->
+    <div class="bg-container border border-primary rounded-lg p-4">
+      <div class="flex items-center gap-2 mb-2">
+        <%= icon("trending-up", size: "sm", class: "text-green-600") %>
+        <h3 class="text-sm font-medium text-secondary">Contributions</h3>
+      </div>
+      <div class="text-2xl font-semibold" style="color: rgb(34 197 94);">
+        <%= format_money(investment_flows.contributions) %>
+      </div>
+      <p class="text-xs text-secondary mt-1">Money added to investments</p>
+    </div>
+
+    <!-- Withdrawals -->
+    <div class="bg-container border border-primary rounded-lg p-4">
+      <div class="flex items-center gap-2 mb-2">
+        <%= icon("trending-down", size: "sm", class: "text-orange-600") %>
+        <h3 class="text-sm font-medium text-secondary">Withdrawals</h3>
+      </div>
+      <div class="text-2xl font-semibold" style="color: rgb(249 115 22);">
+        <%= format_money(investment_flows.withdrawals) %>
+      </div>
+      <p class="text-xs text-secondary mt-1">Money withdrawn from investments</p>
+    </div>
+
+    <!-- Net Flow -->
+    <div class="bg-container border border-primary rounded-lg p-4">
+      <div class="flex items-center gap-2 mb-2">
+        <%= icon("arrow-right-left", size: "sm", class: "text-primary") %>
+        <h3 class="text-sm font-medium text-secondary">Net Flow</h3>
+      </div>
+      <div class="text-2xl font-semibold text-primary">
+        <%= format_money(investment_flows.net_flow) %>
+      </div>
+      <p class="text-xs text-secondary mt-1">Total net change</p>
+    </div>
+  </div>
+</div>
diff --git a/app/views/trades/_trade.html.erb b/app/views/trades/_trade.html.erb
index 30a38226b..d768430e6 100644
--- a/app/views/trades/_trade.html.erb
+++ b/app/views/trades/_trade.html.erb
@@ -27,7 +27,7 @@
             </div>
 
             <div class="flex lg:hidden">
-              <%= render "categories/badge_mobile", category: trade.category || trade_category %>
+              <%= render "investment_activity/quick_edit_badge", entry: entry, entryable: trade %>
             </div>
 
             <div class="truncate flex-shrink">
@@ -40,8 +40,8 @@
         </div>
       </div>
 
-      <div class="hidden lg:flex">
-        <%= render "categories/badge", category: trade.category || trade_category %>
+      <div class="hidden lg:flex col-span-2 items-center">
+        <%= render "investment_activity/quick_edit_badge", entry: entry, entryable: trade %>
       </div>
 
       <div class="shrink-0 col-span-4 lg:col-span-2 ml-auto text-right">
diff --git a/app/views/trades/show.html.erb b/app/views/trades/show.html.erb
index 9d5cf3d03..227470fba 100644
--- a/app/views/trades/show.html.erb
+++ b/app/views/trades/show.html.erb
@@ -43,11 +43,6 @@
                   step: "any",
                   precision: 10,
                   disabled: @entry.linked? %>
-
-            <%= ef.select :category_id,
-                  Current.family.categories.expenses.alphabetically.map { |c| [c.name, c.id] },
-                  { include_blank: t(".no_category"), label: t(".category_label") },
-                  { data: { "auto-submit-form-target": "auto" } } %>
           <% end %>
         <% end %>
       </div>
diff --git a/app/views/transactions/_transaction.html.erb b/app/views/transactions/_transaction.html.erb
index 5eb0b822b..3b30d1b3a 100644
--- a/app/views/transactions/_transaction.html.erb
+++ b/app/views/transactions/_transaction.html.erb
@@ -78,13 +78,6 @@
                       </span>
                     <% end %>
 
-                    <%# Investment activity label badge %>
-                    <% if transaction.investment_activity_label.present? %>
-                      <span class="inline-flex items-center px-1.5 py-0.5 rounded text-xs font-medium bg-alpha-black-50 text-secondary" title="<%= t("transactions.transaction.activity_type_tooltip") %>">
-                        <%= t("transactions.activity_labels.#{transaction.investment_activity_label.parameterize(separator: '_')}") %>
-                      </span>
-                    <% end %>
-
                     <%# Pending indicator %>
                     <% if transaction.pending? %>
                       <span class="inline-flex items-center gap-1 text-xs font-medium rounded-full px-1.5 py-0.5 border border-secondary text-secondary" title="<%= t("transactions.transaction.pending_tooltip") %>">
@@ -144,7 +137,12 @@
       </div>
 
       <div class="hidden md:flex items-center gap-1 col-span-2">
-        <%= render "transactions/transaction_category", transaction: transaction, variant: "desktop" %>
+        <% if entry.account.investment? && !transaction.transfer? %>
+          <%# For investment accounts, show activity label instead of category %>
+          <%= render "investment_activity/quick_edit_badge", entry: entry, entryable: transaction %>
+        <% else %>
+          <%= render "transactions/transaction_category", transaction: transaction, variant: "desktop" %>
+        <% end %>
       </div>
 
       <div class="shrink-0 col-span-4 lg:col-span-2 ml-auto text-right">
diff --git a/app/views/transactions/convert_to_trade.html.erb b/app/views/transactions/convert_to_trade.html.erb
new file mode 100644
index 000000000..4c26097bc
--- /dev/null
+++ b/app/views/transactions/convert_to_trade.html.erb
@@ -0,0 +1,141 @@
+<%
+  # Use activity_label param if provided (from quick-edit badge click),
+  # otherwise determine default based on amount sign
+  # Negative amount (money going out) = Buy, Positive (money coming in) = Sell
+  default_label = params[:activity_label].presence || (@entry.amount > 0 ? "Sell" : "Buy")
+
+  # Get unique securities from account holdings for ticker suggestions
+  account_securities = @entry.account.holdings
+    .includes(:security)
+    .where.not(security: nil)
+    .map(&:security)
+    .uniq(&:ticker)
+    .sort_by(&:ticker)
+%>
+
+<%= render DS::Dialog.new(variant: "modal", reload_on_close: true) do |dialog| %>
+  <% dialog.with_header do %>
+    <h2 class="text-lg font-semibold text-primary"><%= t(".title") %></h2>
+    <p class="text-sm text-secondary"><%= t(".description") %></p>
+  <% end %>
+
+  <% dialog.with_body do %>
+    <%= form_with url: create_trade_from_transaction_transaction_path(@transaction), method: :post, class: "space-y-4", data: { controller: "convert-to-trade", turbo_frame: "_top" } do |f| %>
+      <!-- Pre-filled Transaction Info (Read-only) -->
+      <div class="space-y-2 p-3 bg-surface-inset rounded-lg border border-primary">
+        <div class="text-sm">
+          <span class="text-secondary"><%= t(".date_label") %></span>
+          <span class="font-medium text-primary"><%= @entry.date.strftime("%b %d, %Y") %></span>
+        </div>
+        <div class="text-sm">
+          <span class="text-secondary"><%= t(".account_label") %></span>
+          <span class="font-medium text-primary"><%= @entry.account.name %></span>
+        </div>
+        <div class="text-sm">
+          <span class="text-secondary"><%= t(".amount_label") %></span>
+          <span class="font-medium <%= @entry.amount.negative? ? "text-green-600" : "text-primary" %>"><%= format_money(@entry.amount_money.abs) %></span>
+        </div>
+      </div>
+
+      <!-- Trade-Specific Fields -->
+      <div class="space-y-4">
+        <div class="space-y-1">
+          <%= f.label :security_id, t(".security_label"), class: "font-medium text-sm text-primary block" %>
+          <% if account_securities.any? %>
+            <%= f.select :security_id,
+                  options_for_select(
+                    [[t(".security_prompt"), ""]] +
+                    account_securities.map { |s| ["#{s.ticker}#{s.name.present? ? " - #{s.name.truncate(30)}" : ""}", s.id] } +
+                    [[t(".security_custom"), "__custom__"]],
+                    nil
+                  ),
+                  {},
+                  {
+                    class: "form-field__input border border-secondary rounded-lg px-3 py-2 w-full text-primary bg-container",
+                    data: {
+                      action: "change->convert-to-trade#toggleCustomTicker",
+                      convert_to_trade_target: "tickerSelect"
+                    }
+                  } %>
+            <div class="hidden mt-2" data-convert-to-trade-target="customWrapper">
+              <%= f.text_field :custom_ticker,
+                    placeholder: t(".ticker_placeholder"),
+                    class: "form-field__input border border-secondary rounded-lg px-3 py-2 w-full text-primary bg-container",
+                    pattern: "[A-Za-z0-9.:-]{1,20}",
+                    title: t(".ticker_hint"),
+                    data: { convert_to_trade_target: "customField" } %>
+            </div>
+            <p class="text-xs text-secondary"><%= t(".security_hint") %></p>
+          <% else %>
+            <%= f.text_field :ticker,
+                  placeholder: t(".ticker_placeholder"),
+                  required: true,
+                  class: "form-field__input border border-secondary rounded-lg px-3 py-2 w-full text-primary bg-container",
+                  pattern: "[A-Za-z0-9.:-]{1,20}",
+                  title: t(".ticker_hint") %>
+            <p class="text-xs text-secondary"><%= t(".ticker_hint") %></p>
+          <% end %>
+        </div>
+
+        <div class="grid grid-cols-2 gap-4">
+          <div class="space-y-1">
+            <%= f.label :qty, t(".quantity_label"), class: "font-medium text-sm text-primary block" %>
+            <%= f.number_field :qty,
+                  step: "any",
+                  placeholder: t(".quantity_placeholder"),
+                  class: "form-field__input border border-secondary rounded-lg px-3 py-2 w-full text-primary bg-container" %>
+            <p class="text-xs text-secondary"><%= t(".quantity_hint") %></p>
+          </div>
+
+          <div class="space-y-1">
+            <%= f.label :price, t(".price_label"), class: "font-medium text-sm text-primary block" %>
+            <%= f.number_field :price,
+                  step: "0.0001",
+                  min: "0",
+                  placeholder: t(".price_placeholder"),
+                  class: "form-field__input border border-secondary rounded-lg px-3 py-2 w-full text-primary bg-container" %>
+            <p class="text-xs text-secondary"><%= t(".price_hint", currency: @entry.currency) %></p>
+          </div>
+        </div>
+
+        <p class="text-xs text-secondary bg-surface-inset p-2 rounded">
+          <%= icon "info", size: "xs", class: "inline-block mr-1" %>
+          <%= t(".qty_or_price_hint", amount: format_money(@entry.amount_money.abs)) %>
+        </p>
+
+        <div class="space-y-1">
+          <%= f.label :investment_activity_label, t(".trade_type_label"), class: "font-medium text-sm text-primary block" %>
+          <%= f.select :investment_activity_label,
+                options_for_select([[t("transactions.activity_labels.buy"), "Buy"], [t("transactions.activity_labels.sell"), "Sell"]], default_label),
+                {},
+                { class: "form-field__input border border-secondary rounded-lg px-3 py-2 w-full text-primary bg-container" } %>
+          <p class="text-xs text-secondary"><%= t(".trade_type_hint") %></p>
+        </div>
+
+        <div class="space-y-1">
+          <%= f.label :exchange_operating_mic, t(".exchange_label"), class: "font-medium text-sm text-primary block" %>
+          <%= f.text_field :exchange_operating_mic,
+                placeholder: t(".exchange_placeholder"),
+                class: "form-field__input border border-secondary rounded-lg px-3 py-2 w-full text-primary bg-container",
+                pattern: "[A-Z]{4}",
+                title: t(".exchange_hint") %>
+          <p class="text-xs text-secondary"><%= t(".exchange_hint") %></p>
+        </div>
+      </div>
+
+      <div class="flex justify-end gap-3 pt-4 border-t border-primary">
+        <%= render DS::Button.new(
+          text: t(".cancel"),
+          variant: "outline",
+          href: "#",
+          data: { action: "click->ds--dialog#close" }
+        ) %>
+        <%= render DS::Button.new(
+          text: t(".submit"),
+          variant: "primary",
+          type: "submit"
+        ) %>
+      </div>
+    <% end %>
+  <% end %>
+<% end %>
diff --git a/app/views/transactions/show.html.erb b/app/views/transactions/show.html.erb
index 3d8910dcb..4fa75711d 100644
--- a/app/views/transactions/show.html.erb
+++ b/app/views/transactions/show.html.erb
@@ -265,6 +265,25 @@
           ) %>
         </div>
 
+        <!-- Convert to Trade (Investment Accounts Only, not already converted) -->
+        <% if @entry.account.investment? && @entry.entryable.is_a?(Transaction) && !@entry.excluded? %>
+          <div class="flex items-center justify-between gap-2 p-3">
+            <div class="text-sm space-y-1">
+              <h4 class="text-primary">Convert to Security Trade</h4>
+              <p class="text-secondary">Convert this transaction into a security trade (buy/sell) by providing ticker, shares, and price.</p>
+            </div>
+
+            <%= render DS::Button.new(
+              text: "Convert",
+              variant: "outline",
+              icon: "arrow-right-left",
+              href: convert_to_trade_transaction_path(@entry.transaction),
+              method: :get,
+              frame: :modal
+            ) %>
+          </div>
+        <% end %>
+
         <!-- Mark as Recurring Form -->
         <div class="flex items-center justify-between gap-2 p-3">
           <div class="text-sm space-y-1">
diff --git a/config/locales/views/reports/en.yml b/config/locales/views/reports/en.yml
index ceebbe74c..189a99ebe 100644
--- a/config/locales/views/reports/en.yml
+++ b/config/locales/views/reports/en.yml
@@ -134,6 +134,12 @@ en:
       value: Value
       return: Return
       accounts: Investment Accounts
+    investment_flows:
+      title: Investment Flows
+      description: Track money flowing into and out of your investment accounts
+      contributions: Contributions
+      withdrawals: Withdrawals
+      net_flow: Net Flow
     google_sheets_instructions:
       title_with_key: "✅ Copy URL for Google Sheets"
       title_no_key: "⚠️ API Key Required"
diff --git a/config/locales/views/transactions/en.yml b/config/locales/views/transactions/en.yml
index ae7bb1cb3..35eb2308e 100644
--- a/config/locales/views/transactions/en.yml
+++ b/config/locales/views/transactions/en.yml
@@ -37,6 +37,9 @@ en:
       activity_type_description: Type of investment activity (Buy, Sell, Dividend, etc.). Auto-detected or set manually.
       one_time_title: One-time %{type}
       one_time_description: One-time transactions will be excluded from certain budgeting calculations and reports to help you see what's really important.
+      convert_to_trade_title: Convert to Security Trade
+      convert_to_trade_description: Convert this transaction into a Buy or Sell trade with security details for portfolio tracking.
+      convert_to_trade_button: Convert to Trade
     activity_labels:
       buy: Buy
       sell: Sell
@@ -103,6 +106,43 @@ en:
         category: Category
         tag: Tag
         merchant: Merchant
+    convert_to_trade:
+      title: Convert to Security Trade
+      description: Convert this transaction into a trade with security details
+      date_label: "Date:"
+      account_label: "Account:"
+      amount_label: "Amount:"
+      security_label: Security
+      security_prompt: Select a security...
+      security_custom: "+ Enter custom ticker"
+      security_hint: Select from your holdings or enter a custom ticker
+      ticker_placeholder: AAPL
+      ticker_hint: Enter the stock/ETF ticker symbol
+      quantity_label: Quantity (Shares)
+      quantity_placeholder: e.g. 20
+      quantity_hint: Number of shares traded
+      price_label: Price per Share
+      price_placeholder: e.g. 52.15
+      price_hint: Price per share (%{currency})
+      qty_or_price_hint: Enter at least qty OR price. The other will be calculated from the transaction amount (%{amount}).
+      trade_type_label: Trade Type
+      trade_type_hint: Buy or Sell shares of a security
+      exchange_label: Exchange (Optional)
+      exchange_placeholder: XNAS
+      exchange_hint: Leave blank to auto-detect
+      cancel: Cancel
+      submit: Convert to Trade
+      success: Transaction converted to trade
+      errors:
+        not_investment_account: Only transactions in investment accounts can be converted to trades
+        already_converted: This transaction has already been converted or excluded
+        enter_ticker: Please enter a ticker symbol
+        security_not_found: Selected security no longer exists. Please select another.
+        select_security: Please select or enter a security
+        enter_qty_or_price: Please enter either quantity or price per share. The other will be calculated from the transaction amount.
+        invalid_qty_or_price: Invalid quantity or price. Please enter valid positive values.
+        conversion_failed: "Failed to convert transaction: %{error}"
+        unexpected_error: "Unexpected error during conversion: %{error}"
     searches:
       filters:
         amount_filter:
diff --git a/config/routes.rb b/config/routes.rb
index 07a70144e..0106f6d17 100644
--- a/config/routes.rb
+++ b/config/routes.rb
@@ -197,6 +197,8 @@ Rails.application.routes.draw do
     end
 
     member do
+      get :convert_to_trade
+      post :create_trade_from_transaction
       post :mark_as_recurring
       post :merge_duplicate
       post :dismiss_duplicate
diff --git a/db/migrate/20260113230414_add_investment_activity_label_to_trades.rb b/db/migrate/20260113230414_add_investment_activity_label_to_trades.rb
new file mode 100644
index 000000000..9e8e3e8a8
--- /dev/null
+++ b/db/migrate/20260113230414_add_investment_activity_label_to_trades.rb
@@ -0,0 +1,22 @@
+class AddInvestmentActivityLabelToTrades < ActiveRecord::Migration[7.2]
+  def change
+    # Add activity label to trades (matching Transaction)
+    add_column :trades, :investment_activity_label, :string
+    add_index :trades, :investment_activity_label
+
+    # Backfill existing trades with basic labels based on quantity
+    reversible do |dir|
+      dir.up do
+        execute <<~SQL
+          UPDATE trades
+          SET investment_activity_label = CASE
+            WHEN qty > 0 THEN 'Buy'
+            WHEN qty < 0 THEN 'Sell'
+            ELSE 'Other'
+          END
+          WHERE investment_activity_label IS NULL
+        SQL
+      end
+    end
+  end
+end
diff --git a/db/migrate/20260114002048_remove_category_from_trades.rb b/db/migrate/20260114002048_remove_category_from_trades.rb
new file mode 100644
index 000000000..333f910d6
--- /dev/null
+++ b/db/migrate/20260114002048_remove_category_from_trades.rb
@@ -0,0 +1,5 @@
+class RemoveCategoryFromTrades < ActiveRecord::Migration[7.2]
+  def change
+    remove_column :trades, :category_id, :bigint
+  end
+end
diff --git a/db/schema.rb b/db/schema.rb
index fe90f4ce2..4e123a2ab 100644
--- a/db/schema.rb
+++ b/db/schema.rb
@@ -1183,14 +1183,14 @@ ActiveRecord::Schema[7.2].define(version: 2026_01_15_100001) do
     t.datetime "updated_at", null: false
     t.string "currency"
     t.jsonb "locked_attributes", default: {}
-    t.uuid "category_id"
     t.decimal "realized_gain", precision: 19, scale: 4
     t.decimal "cost_basis_amount", precision: 19, scale: 4
     t.string "cost_basis_currency"
     t.integer "holding_period_days"
     t.string "realized_gain_confidence"
     t.string "realized_gain_currency"
-    t.index ["category_id"], name: "index_trades_on_category_id"
+    t.string "investment_activity_label"
+    t.index ["investment_activity_label"], name: "index_trades_on_investment_activity_label"
     t.index ["realized_gain"], name: "index_trades_on_realized_gain_not_null", where: "(realized_gain IS NOT NULL)"
     t.index ["security_id"], name: "index_trades_on_security_id"
   end
@@ -1348,7 +1348,6 @@ ActiveRecord::Schema[7.2].define(version: 2026_01_15_100001) do
   add_foreign_key "taggings", "tags"
   add_foreign_key "tags", "families"
   add_foreign_key "tool_calls", "messages"
-  add_foreign_key "trades", "categories"
   add_foreign_key "trades", "securities"
   add_foreign_key "transactions", "categories", on_delete: :nullify
   add_foreign_key "transactions", "merchants"
diff --git a/test/fixtures/trades.yml b/test/fixtures/trades.yml
index bf1acd710..d421b51cc 100644
--- a/test/fixtures/trades.yml
+++ b/test/fixtures/trades.yml
@@ -3,3 +3,4 @@ one:
   qty: 10
   price: 214
   currency: USD
+  investment_activity_label: Buy
diff --git a/test/models/account/market_data_importer_test.rb b/test/models/account/market_data_importer_test.rb
index 828f34814..eead24bd5 100644
--- a/test/models/account/market_data_importer_test.rb
+++ b/test/models/account/market_data_importer_test.rb
@@ -79,7 +79,7 @@ class Account::MarketDataImporterTest < ActiveSupport::TestCase
     security = Security.create!(ticker: "AAPL", exchange_operating_mic: "XNAS")
 
     trade_date = 10.days.ago.to_date
-    trade      = Trade.new(security: security, qty: 1, price: 100, currency: "USD")
+    trade      = Trade.new(security: security, qty: 1, price: 100, currency: "USD", investment_activity_label: "Buy")
 
     account.entries.create!(
       name: "Buy AAPL",
@@ -129,7 +129,7 @@ class Account::MarketDataImporterTest < ActiveSupport::TestCase
     security = Security.create!(ticker: "INVALID", exchange_operating_mic: "XNAS")
 
     trade_date = 10.days.ago.to_date
-    trade      = Trade.new(security: security, qty: 1, price: 100, currency: "USD")
+    trade      = Trade.new(security: security, qty: 1, price: 100, currency: "USD", investment_activity_label: "Buy")
 
     account.entries.create!(
       name: "Buy INVALID",
diff --git a/test/models/trade_import_test.rb b/test/models/trade_import_test.rb
index 7914fe932..3fbdd3c11 100644
--- a/test/models/trade_import_test.rb
+++ b/test/models/trade_import_test.rb
@@ -63,20 +63,13 @@ class TradeImportTest < ActiveSupport::TestCase
     assert_equal "complete", @import.status
   end
 
-  test "auto-categorizes buy trades and leaves sell trades uncategorized" do
+  test "auto-assigns investment activity labels to buy and sell trades" do
     aapl = securities(:aapl)
     aapl_resolver = mock
     aapl_resolver.stubs(:resolve).returns(aapl)
     Security::Resolver.stubs(:new).returns(aapl_resolver)
 
-    # Create the investment category if it doesn't exist
     account = accounts(:depository)
-    family = account.family
-    savings_category = family.categories.find_or_create_by!(name: "Savings & Investments") do |c|
-      c.color = "#059669"
-      c.classification = "expense"
-      c.lucide_icon = "piggy-bank"
-    end
 
     import = <<~CSV
       date,ticker,qty,price,currency,name
@@ -109,7 +102,7 @@ class TradeImportTest < ActiveSupport::TestCase
 
     assert_not_nil buy_trade, "Buy trade should have been created"
     assert_not_nil sell_trade, "Sell trade should have been created"
-    assert_equal savings_category, buy_trade.category, "Buy trade should be auto-categorized as Savings & Investments"
-    assert_nil sell_trade.category, "Sell trade should not be auto-categorized"
+    assert_equal "Buy", buy_trade.investment_activity_label, "Buy trade should have 'Buy' activity label"
+    assert_equal "Sell", sell_trade.investment_activity_label, "Sell trade should have 'Sell' activity label"
   end
 end
diff --git a/test/models/trade_test.rb b/test/models/trade_test.rb
index c86f44210..ab8ba56ba 100644
--- a/test/models/trade_test.rb
+++ b/test/models/trade_test.rb
@@ -30,7 +30,8 @@ class TradeTest < ActiveSupport::TestCase
       security: security,
       price: precise_price,
       qty: 10000,
-      currency: "USD"
+      currency: "USD",
+      investment_activity_label: "Buy"
     )
 
     trade.reload
@@ -47,7 +48,8 @@ class TradeTest < ActiveSupport::TestCase
       security: security,
       price: price_with_too_many_decimals,
       qty: 1,
-      currency: "USD"
+      currency: "USD",
+      investment_activity_label: "Buy"
     )
 
     trade.reload
diff --git a/test/support/entries_test_helper.rb b/test/support/entries_test_helper.rb
index f586b1488..90ecd9220 100644
--- a/test/support/entries_test_helper.rb
+++ b/test/support/entries_test_helper.rb
@@ -41,7 +41,8 @@ module EntriesTestHelper
       qty: qty,
       security: security,
       price: trade_price,
-      currency: currency
+      currency: currency,
+      investment_activity_label: qty > 0 ? "Buy" : "Sell"
 
     account.entries.create! \
       name: "Trade",
diff --git a/test/support/ledger_testing_helper.rb b/test/support/ledger_testing_helper.rb
index d5e08aec4..a2266b679 100644
--- a/test/support/ledger_testing_helper.rb
+++ b/test/support/ledger_testing_helper.rb
@@ -77,7 +77,8 @@ module LedgerTestingHelper
           qty: entry_data[:qty],
           security: security,
           price: entry_data[:price],
-          currency: currency
+          currency: currency,
+          investment_activity_label: entry_data[:qty] > 0 ? "Buy" : "Sell"
         )
 
         created_account.entries.create!(