diff --git a/app/models/family/auto_categorizer.rb b/app/models/family/auto_categorizer.rb
index 25fde493..1ac8b874 100644
--- a/app/models/family/auto_categorizer.rb
+++ b/app/models/family/auto_categorizer.rb
@@ -70,8 +70,7 @@ class Family::AutoCategorizer
           amount: transaction.entry.amount.abs,
           classification: transaction.entry.classification,
           description: transaction.entry.name,
-          merchant: transaction.merchant&.name,
-          hint: transaction.plaid_category_detailed
+          merchant: transaction.merchant&.name
         }
       end
     end
diff --git a/app/models/plaid_account/investments/holdings_processor.rb b/app/models/plaid_account/investments/holdings_processor.rb
index b5671151..cfaaa5b3 100644
--- a/app/models/plaid_account/investments/holdings_processor.rb
+++ b/app/models/plaid_account/investments/holdings_processor.rb
@@ -27,7 +27,7 @@ class PlaidAccount::Investments::HoldingsProcessor
   end
 
   private
-    attr_reader :plaid_account
+    attr_reader :plaid_account, :security_resolver
 
     def account
       plaid_account.account
diff --git a/app/models/plaid_account/investments/transactions_processor.rb b/app/models/plaid_account/investments/transactions_processor.rb
index faa285fc..9dcebdb0 100644
--- a/app/models/plaid_account/investments/transactions_processor.rb
+++ b/app/models/plaid_account/investments/transactions_processor.rb
@@ -1,4 +1,6 @@
 class PlaidAccount::Investments::TransactionsProcessor
+  SecurityNotFoundError = Class.new(StandardError)
+
   def initialize(plaid_account, security_resolver:)
     @plaid_account = plaid_account
     @security_resolver = security_resolver
@@ -6,12 +8,10 @@ class PlaidAccount::Investments::TransactionsProcessor
 
   def process
     transactions.each do |transaction|
-      resolved_security_result = security_resolver.resolve(plaid_security_id: transaction["security_id"])
-
-      if resolved_security_result.security.present?
-        find_or_create_trade_entry(transaction)
-      else
+      if cash_transaction?(transaction)
         find_or_create_cash_entry(transaction)
+      else
+        find_or_create_trade_entry(transaction)
       end
     end
   end
@@ -23,17 +23,25 @@ class PlaidAccount::Investments::TransactionsProcessor
       plaid_account.account
     end
 
+    def cash_transaction?(transaction)
+      transaction["type"] == "cash" || transaction["type"] == "fee"
+    end
+
     def find_or_create_trade_entry(transaction)
+      resolved_security_result = security_resolver.resolve(plaid_security_id: transaction["security_id"])
+
+      unless resolved_security_result.security.present?
+        Sentry.capture_exception(SecurityNotFoundError.new("Could not find security for plaid trade")) do |scope|
+          scope.set_tags(plaid_account_id: plaid_account.id)
+        end
+
+        return # We can't process a non-cash transaction without a security
+      end
+
       entry = account.entries.find_or_initialize_by(plaid_id: transaction["investment_transaction_id"]) do |e|
         e.entryable = Trade.new
       end
 
-      entry.enrich_attribute(
-        :name,
-        transaction["name"],
-        source: "plaid"
-      )
-
       entry.assign_attributes(
         amount: transaction["quantity"] * transaction["price"],
         currency: transaction["iso_currency_code"],
@@ -41,12 +49,18 @@ class PlaidAccount::Investments::TransactionsProcessor
       )
 
       entry.trade.assign_attributes(
-        security: security,
+        security: resolved_security_result.security,
         qty: transaction["quantity"],
         price: transaction["price"],
         currency: transaction["iso_currency_code"]
       )
 
+      entry.enrich_attribute(
+        :name,
+        transaction["name"],
+        source: "plaid"
+      )
+
       entry.save!
     end
 
@@ -55,18 +69,18 @@ class PlaidAccount::Investments::TransactionsProcessor
         e.entryable = Transaction.new
       end
 
-      entry.enrich_attribute(
-        :name,
-        transaction["name"],
-        source: "plaid"
-      )
-
       entry.assign_attributes(
         amount: transaction["amount"],
         currency: transaction["iso_currency_code"],
         date: transaction["date"]
       )
 
+      entry.enrich_attribute(
+        :name,
+        transaction["name"],
+        source: "plaid"
+      )
+
       entry.save!
     end
 
diff --git a/app/models/plaid_account/transactions/processor.rb b/app/models/plaid_account/transactions/processor.rb
index 155b12fe..8aa07162 100644
--- a/app/models/plaid_account/transactions/processor.rb
+++ b/app/models/plaid_account/transactions/processor.rb
@@ -6,7 +6,7 @@ class PlaidAccount::Transactions::Processor
   def process
     # Each entry is processed inside a transaction, but to avoid locking up the DB when
     # there are hundreds or thousands of transactions, we process them individually.
-    modified_transactions.find_each do |transaction|
+    modified_transactions.each do |transaction|
       PlaidEntry::Processor.new(
         transaction,
         plaid_account: plaid_account,
@@ -15,7 +15,7 @@ class PlaidAccount::Transactions::Processor
     end
 
     PlaidAccount.transaction do
-      removed_transactions.find_each do |transaction|
+      removed_transactions.each do |transaction|
         remove_plaid_transaction(transaction)
       end
     end
diff --git a/test/models/plaid_account/investments/holdings_processor_test.rb b/test/models/plaid_account/investments/holdings_processor_test.rb
index 5d0a06ab..ac5b5895 100644
--- a/test/models/plaid_account/investments/holdings_processor_test.rb
+++ b/test/models/plaid_account/investments/holdings_processor_test.rb
@@ -2,14 +2,48 @@ require "test_helper"
 
 class PlaidAccount::Investments::HoldingsProcessorTest < ActiveSupport::TestCase
   setup do
-    # TODO: set up holdings data and security resolver stub
+    @plaid_account = plaid_accounts(:one)
+    @security_resolver = PlaidAccount::Investments::SecurityResolver.new(@plaid_account)
   end
 
   test "creates holding records from Plaid holdings snapshot" do
-    # TODO
-  end
+    test_investments_payload = {
+      securities: [], # mocked
+      holdings: [
+        {
+          "security_id" => "123",
+          "quantity" => 100,
+          "institution_price" => 100,
+          "iso_currency_code" => "USD"
+        }
+      ],
+      transactions: [] # not relevant for test
+    }
 
-  test "upserts security records via SecurityResolver" do
-    # TODO
+    @plaid_account.update!(raw_investments_payload: test_investments_payload)
+
+    @security_resolver.expects(:resolve)
+                      .with(plaid_security_id: "123")
+                      .returns(
+                        OpenStruct.new(
+                          security: securities(:aapl),
+                          cash_equivalent?: false,
+                          brokerage_cash?: false
+                        )
+                      )
+
+    processor = PlaidAccount::Investments::HoldingsProcessor.new(@plaid_account, security_resolver: @security_resolver)
+
+    assert_difference "Holding.count" do
+      processor.process
+    end
+
+    holding = Holding.order(created_at: :desc).first
+
+    assert_equal 100, holding.qty
+    assert_equal 100, holding.price
+    assert_equal "USD", holding.currency
+    assert_equal securities(:aapl), holding.security
+    assert_equal Date.current, holding.date
   end
 end
diff --git a/test/models/plaid_account/investments/security_resolver_test.rb b/test/models/plaid_account/investments/security_resolver_test.rb
index d154d536..a32430c6 100644
--- a/test/models/plaid_account/investments/security_resolver_test.rb
+++ b/test/models/plaid_account/investments/security_resolver_test.rb
@@ -2,14 +2,114 @@ require "test_helper"
 
 class PlaidAccount::Investments::SecurityResolverTest < ActiveSupport::TestCase
   setup do
-    # TODO: stub security provider lookup
+    @upstream_resolver = mock("Security::Resolver")
+    @plaid_account = plaid_accounts(:one)
+    @resolver = PlaidAccount::Investments::SecurityResolver.new(@plaid_account)
   end
 
-  test "finds existing security by identifiers" do
-    # TODO
+  test "handles missing plaid security" do
+    missing_id = "missing_security_id"
+
+    # Ensure there are *no* securities that reference the missing ID
+    @plaid_account.update!(raw_investments_payload: {
+      securities: [
+        {
+          "security_id" => "some_other_id",
+          "ticker_symbol" => "FOO",
+          "type" => "equity",
+          "market_identifier_code" => "XNAS"
+        }
+      ]
+    })
+
+    Security::Resolver.expects(:new).never
+    Sentry.stubs(:capture_exception)
+
+    response = @resolver.resolve(plaid_security_id: missing_id)
+
+    assert_nil response.security
+    refute response.cash_equivalent?
+    refute response.brokerage_cash?
   end
 
-  test "creates new security when none found" do
-    # TODO
+  test "identifies brokerage cash plaid securities" do
+    brokerage_cash_id = "brokerage_cash_security_id"
+
+    @plaid_account.update!(raw_investments_payload: {
+      securities: [
+        {
+          "security_id" => brokerage_cash_id,
+          "ticker_symbol" => "CUR:USD", # Plaid brokerage cash ticker
+          "type" => "cash",
+          "is_cash_equivalent" => true
+        }
+      ]
+    })
+
+    Security::Resolver.expects(:new).never
+
+    response = @resolver.resolve(plaid_security_id: brokerage_cash_id)
+
+    assert_nil response.security
+    assert response.cash_equivalent?
+    assert response.brokerage_cash?
+  end
+
+  test "identifies cash equivalent plaid securities" do
+    mmf_security_id = "money_market_security_id"
+
+    @plaid_account.update!(raw_investments_payload: {
+      securities: [
+        {
+          "security_id" => mmf_security_id,
+          "ticker_symbol" => "VMFXX", # Vanguard Federal Money Market Fund
+          "type" => "mutual fund",
+          "is_cash_equivalent" => true,
+          "market_identifier_code" => "XNAS"
+        }
+      ]
+    })
+
+    resolved_security = Security.create!(ticker: "VMFXX", exchange_operating_mic: "XNAS")
+
+    Security::Resolver.expects(:new)
+                     .with("VMFXX", exchange_operating_mic: "XNAS")
+                     .returns(@upstream_resolver)
+    @upstream_resolver.expects(:resolve).returns(resolved_security)
+
+    response = @resolver.resolve(plaid_security_id: mmf_security_id)
+
+    assert_equal resolved_security, response.security
+    assert response.cash_equivalent?
+    refute response.brokerage_cash?
+  end
+
+  test "resolves normal plaid securities" do
+    security_id = "regular_security_id"
+
+    @plaid_account.update!(raw_investments_payload: {
+      securities: [
+        {
+          "security_id" => security_id,
+          "ticker_symbol" => "IVV",
+          "type" => "etf",
+          "is_cash_equivalent" => false,
+          "market_identifier_code" => "XNAS"
+        }
+      ]
+    })
+
+    resolved_security = Security.create!(ticker: "IVV", exchange_operating_mic: "XNAS")
+
+    Security::Resolver.expects(:new)
+                     .with("IVV", exchange_operating_mic: "XNAS")
+                     .returns(@upstream_resolver)
+    @upstream_resolver.expects(:resolve).returns(resolved_security)
+
+    response = @resolver.resolve(plaid_security_id: security_id)
+
+    assert_equal resolved_security, response.security
+    refute response.cash_equivalent? # Normal securities are not cash equivalent
+    refute response.brokerage_cash?
   end
 end
diff --git a/test/models/plaid_account/investments/transactions_processor_test.rb b/test/models/plaid_account/investments/transactions_processor_test.rb
index a377865b..8a0c9efd 100644
--- a/test/models/plaid_account/investments/transactions_processor_test.rb
+++ b/test/models/plaid_account/investments/transactions_processor_test.rb
@@ -2,14 +2,110 @@ require "test_helper"
 
 class PlaidAccount::Investments::TransactionsProcessorTest < ActiveSupport::TestCase
   setup do
-    # TODO: set up investment plaid account and security resolver stub
+    @plaid_account = plaid_accounts(:one)
+    @security_resolver = PlaidAccount::Investments::SecurityResolver.new(@plaid_account)
   end
 
-  test "creates trade entries from Plaid investment transactions" do
-    # TODO
+
+  test "creates regular trade entries" do
+    test_investments_payload = {
+      transactions: [
+        {
+          "transaction_id" => "123",
+          "security_id" => "123",
+          "type" => "buy",
+          "quantity" => 1, # Positive, so "buy 1 share"
+          "price" => 100,
+          "iso_currency_code" => "USD",
+          "date" => Date.current,
+          "name" => "Buy 1 share of AAPL"
+        }
+      ]
+    }
+
+    @plaid_account.update!(raw_investments_payload: test_investments_payload)
+
+    @security_resolver.stubs(:resolve).returns(OpenStruct.new(
+      security: securities(:aapl)
+    ))
+
+    processor = PlaidAccount::Investments::TransactionsProcessor.new(@plaid_account, security_resolver: @security_resolver)
+
+    assert_difference [ "Entry.count", "Trade.count" ], 1 do
+      processor.process
+    end
+
+    entry = Entry.order(created_at: :desc).first
+
+    assert_equal 100, entry.amount
+    assert_equal "USD", entry.currency
+    assert_equal Date.current, entry.date
+    assert_equal "Buy 1 share of AAPL", entry.name
   end
 
-  test "handles security resolution for unknown securities" do
-    # TODO
+  test "creates cash transactions" do
+    test_investments_payload = {
+      transactions: [
+        {
+          "transaction_id" => "123",
+          "type" => "cash",
+          "subtype" => "withdrawal",
+          "amount" => 100, # Positive, so moving money OUT of the account
+          "iso_currency_code" => "USD",
+          "date" => Date.current,
+          "name" => "Withdrawal"
+        }
+      ]
+    }
+
+    @plaid_account.update!(raw_investments_payload: test_investments_payload)
+
+    @security_resolver.expects(:resolve).never # Cash transactions don't have a security
+
+    processor = PlaidAccount::Investments::TransactionsProcessor.new(@plaid_account, security_resolver: @security_resolver)
+
+    assert_difference [ "Entry.count", "Transaction.count" ], 1 do
+      processor.process
+    end
+
+    entry = Entry.order(created_at: :desc).first
+
+    assert_equal 100, entry.amount
+    assert_equal "USD", entry.currency
+    assert_equal Date.current, entry.date
+    assert_equal "Withdrawal", entry.name
+  end
+
+  test "creates fee transactions" do
+    test_investments_payload = {
+      transactions: [
+        {
+          "transaction_id" => "123",
+          "type" => "fee",
+          "subtype" => "miscellaneous fee",
+          "amount" => 10.25,
+          "iso_currency_code" => "USD",
+          "date" => Date.current,
+          "name" => "Miscellaneous fee"
+        }
+      ]
+    }
+
+    @plaid_account.update!(raw_investments_payload: test_investments_payload)
+
+    @security_resolver.expects(:resolve).never # Cash transactions don't have a security
+
+    processor = PlaidAccount::Investments::TransactionsProcessor.new(@plaid_account, security_resolver: @security_resolver)
+
+    assert_difference [ "Entry.count", "Transaction.count" ], 1 do
+      processor.process
+    end
+
+    entry = Entry.order(created_at: :desc).first
+
+    assert_equal 10.25, entry.amount
+    assert_equal "USD", entry.currency
+    assert_equal Date.current, entry.date
+    assert_equal "Miscellaneous fee", entry.name
   end
 end
diff --git a/test/models/plaid_account/transactions/processor_test.rb b/test/models/plaid_account/transactions/processor_test.rb
index 3c5bc10d..85272b11 100644
--- a/test/models/plaid_account/transactions/processor_test.rb
+++ b/test/models/plaid_account/transactions/processor_test.rb
@@ -15,16 +15,19 @@ class PlaidAccount::Transactions::ProcessorTest < ActiveSupport::TestCase
       removed: []
     })
 
-    mock_processor = mock("PlaidEntry::TransactionProcessor")
-    PlaidEntry::TransactionProcessor.expects(:new)
-                                    .with(added_transactions.first, plaid_account: @plaid_account)
-                                    .returns(mock_processor)
-                                    .once
+    mock_processor = mock("PlaidEntry::Processor")
+    category_matcher_mock = mock("PlaidAccount::Transactions::CategoryMatcher")
 
-    PlaidEntry::TransactionProcessor.expects(:new)
-                                    .with(modified_transactions.first, plaid_account: @plaid_account)
-                                    .returns(mock_processor)
-                                    .once
+    PlaidAccount::Transactions::CategoryMatcher.stubs(:new).returns(category_matcher_mock)
+    PlaidEntry::Processor.expects(:new)
+                         .with(added_transactions.first, plaid_account: @plaid_account, category_matcher: category_matcher_mock)
+                         .returns(mock_processor)
+                         .once
+
+    PlaidEntry::Processor.expects(:new)
+                         .with(modified_transactions.first, plaid_account: @plaid_account, category_matcher: category_matcher_mock)
+                         .returns(mock_processor)
+                         .once
 
     mock_processor.expects(:process).twice