diff --git a/app/models/account/provider_import_adapter.rb b/app/models/account/provider_import_adapter.rb
index 5304b59f8..0c7fc1883 100644
--- a/app/models/account/provider_import_adapter.rb
+++ b/app/models/account/provider_import_adapter.rb
@@ -30,6 +30,7 @@ class Account::ProviderImportAdapter
       # If this is a new entry, check for potential duplicates from manual/CSV imports
       # This handles the case where a user manually created or CSV imported a transaction
       # before linking their account to a provider
+      # Note: We don't pass name here to allow matching even when provider formats names differently
       if entry.new_record?
         duplicate = find_duplicate_transaction(date: date, amount: amount, currency: currency)
         if duplicate
@@ -266,33 +267,41 @@ class Account::ProviderImportAdapter
     false
   end
 
-  private
+  # Finds a potential duplicate transaction from manual entry or CSV import
+  # Matches on date, amount, currency, and optionally name
+  # Only matches transactions without external_id (manual/CSV imported)
+  #
+  # @param date [Date, String] Transaction date
+  # @param amount [BigDecimal, Numeric] Transaction amount
+  # @param currency [String] Currency code
+  # @param name [String, nil] Optional transaction name for more accurate matching
+  # @param exclude_entry_ids [Set, Array, nil] Entry IDs to exclude from the search (e.g., already claimed entries)
+  # @return [Entry, nil] The duplicate entry or nil if not found
+  def find_duplicate_transaction(date:, amount:, currency:, name: nil, exclude_entry_ids: nil)
+    # Convert date to Date object if it's a string
+    date = Date.parse(date.to_s) unless date.is_a?(Date)
 
-    # Finds a potential duplicate transaction from manual entry or CSV import
-    # Matches on date, amount, and currency
-    # Only matches transactions without external_id (manual/CSV imported)
-    #
-    # @param date [Date, String] Transaction date
-    # @param amount [BigDecimal, Numeric] Transaction amount
-    # @param currency [String] Currency code
-    # @return [Entry, nil] The duplicate entry or nil if not found
-    def find_duplicate_transaction(date:, amount:, currency:)
-      # Convert date to Date object if it's a string
-      date = Date.parse(date.to_s) unless date.is_a?(Date)
+    # Look for entries on the same account with:
+    # 1. Same date
+    # 2. Same amount (exact match)
+    # 3. Same currency
+    # 4. No external_id (manual/CSV imported transactions)
+    # 5. Entry type is Transaction (not Trade or Valuation)
+    # 6. Optionally same name (if name parameter is provided)
+    # 7. Not in the excluded IDs list (if provided)
+    query = account.entries
+                   .where(entryable_type: "Transaction")
+                   .where(date: date)
+                   .where(amount: amount)
+                   .where(currency: currency)
+                   .where(external_id: nil)
 
-      # Look for entries on the same account with:
-      # 1. Same date
-      # 2. Same amount (exact match)
-      # 3. Same currency
-      # 4. No external_id (manual/CSV imported transactions)
-      # 5. Entry type is Transaction (not Trade or Valuation)
-      account.entries
-             .where(entryable_type: "Transaction")
-             .where(date: date)
-             .where(amount: amount)
-             .where(currency: currency)
-             .where(external_id: nil)
-             .order(created_at: :asc)
-             .first
-    end
+    # Add name filter if provided
+    query = query.where(name: name) if name.present?
+
+    # Exclude already claimed entries if provided
+    query = query.where.not(id: exclude_entry_ids) if exclude_entry_ids.present?
+
+    query.order(created_at: :asc).first
+  end
 end
diff --git a/app/models/import.rb b/app/models/import.rb
index 5d6bea647..b6e25e416 100644
--- a/app/models/import.rb
+++ b/app/models/import.rb
@@ -1,5 +1,6 @@
 class Import < ApplicationRecord
   MaxRowCountExceededError = Class.new(StandardError)
+  MappingError = Class.new(StandardError)
 
   TYPES = %w[TransactionImport TradeImport AccountImport MintImport].freeze
   SIGNAGE_CONVENTIONS = %w[inflows_positive inflows_negative]
diff --git a/app/models/transaction_import.rb b/app/models/transaction_import.rb
index d233c2e42..5a1adbafa 100644
--- a/app/models/transaction_import.rb
+++ b/app/models/transaction_import.rb
@@ -3,32 +3,76 @@ class TransactionImport < Import
     transaction do
       mappings.each(&:create_mappable!)
 
-      transactions = rows.map do |row|
+      new_transactions = []
+      updated_entries = []
+      claimed_entry_ids = Set.new # Track entries we've already claimed in this import
+
+      rows.each_with_index do |row, index|
         mapped_account = if account
           account
         else
           mappings.accounts.mappable_for(row.account)
         end
 
+        # Guard against nil account - this happens when an account name in CSV is not mapped
+        if mapped_account.nil?
+          row_number = index + 1
+          account_name = row.account.presence || "(blank)"
+          error_message = "Row #{row_number}: Account '#{account_name}' is not mapped to an existing account. " \
+                         "Please map this account in the import configuration."
+          errors.add(:base, error_message)
+          raise Import::MappingError, error_message
+        end
+
         category = mappings.categories.mappable_for(row.category)
         tags = row.tags_list.map { |tag| mappings.tags.mappable_for(tag) }.compact
 
-        Transaction.new(
-          category: category,
-          tags: tags,
-          entry: Entry.new(
-            account: mapped_account,
-            date: row.date_iso,
-            amount: row.signed_amount,
-            name: row.name,
-            currency: row.currency,
-            notes: row.notes,
-            import: self
-          )
+        # Check for duplicate transactions using the adapter's deduplication logic
+        # Pass claimed_entry_ids to exclude entries we've already matched in this import
+        # This ensures identical rows within the CSV are all imported as separate transactions
+        adapter = Account::ProviderImportAdapter.new(mapped_account)
+        duplicate_entry = adapter.find_duplicate_transaction(
+          date: row.date_iso,
+          amount: row.signed_amount,
+          currency: row.currency,
+          name: row.name,
+          exclude_entry_ids: claimed_entry_ids
         )
+
+        if duplicate_entry
+          # Update existing transaction instead of creating a new one
+          duplicate_entry.transaction.category = category if category.present?
+          duplicate_entry.transaction.tags = tags if tags.any?
+          duplicate_entry.notes = row.notes if row.notes.present?
+          duplicate_entry.import = self
+          updated_entries << duplicate_entry
+          claimed_entry_ids.add(duplicate_entry.id)
+        else
+          # Create new transaction (no duplicate found)
+          new_transactions << Transaction.new(
+            category: category,
+            tags: tags,
+            entry: Entry.new(
+              account: mapped_account,
+              date: row.date_iso,
+              amount: row.signed_amount,
+              name: row.name,
+              currency: row.currency,
+              notes: row.notes,
+              import: self
+            )
+          )
+        end
       end
 
-      Transaction.import!(transactions, recursive: true)
+      # Save updated entries first
+      updated_entries.each do |entry|
+        entry.transaction.save!
+        entry.save!
+      end
+
+      # Bulk import new transactions
+      Transaction.import!(new_transactions, recursive: true) if new_transactions.any?
     end
   end
 
diff --git a/test/models/transaction_import_test.rb b/test/models/transaction_import_test.rb
index dc94b20cf..88ebf0acd 100644
--- a/test/models/transaction_import_test.rb
+++ b/test/models/transaction_import_test.rb
@@ -100,4 +100,226 @@ class TransactionImportTest < ActiveSupport::TestCase
 
     assert_equal [ -100, 200, -300 ], @import.entries.map(&:amount)
   end
+
+  test "does not create duplicate when matching transaction exists with same name" do
+    account = accounts(:depository)
+
+    # Create an existing manual transaction
+    existing_entry = account.entries.create!(
+      date: Date.new(2024, 1, 1),
+      amount: 100,
+      currency: "USD",
+      name: "Coffee Shop",
+      entryable: Transaction.new(category: categories(:food_and_drink))
+    )
+
+    # Try to import a CSV with the same transaction
+    import_csv = <<~CSV
+      date,name,amount
+      01/01/2024,Coffee Shop,100
+    CSV
+
+    @import.update!(
+      account: account,
+      raw_file_str: import_csv,
+      date_col_label: "date",
+      amount_col_label: "amount",
+      name_col_label: "name",
+      date_format: "%m/%d/%Y",
+      amount_type_strategy: "signed_amount",
+      signage_convention: "inflows_negative"
+    )
+
+    @import.generate_rows_from_csv
+    @import.reload
+
+    # Should not create a new entry, should update the existing one
+    assert_no_difference -> { Entry.count } do
+      assert_no_difference -> { Transaction.count } do
+        @import.publish
+      end
+    end
+
+    # The existing entry should now be linked to the import
+    assert_equal @import.id, existing_entry.reload.import_id
+  end
+
+  test "creates new transaction when name differs even if date and amount match" do
+    account = accounts(:depository)
+
+    # Create an existing manual transaction
+    existing_entry = account.entries.create!(
+      date: Date.new(2024, 1, 1),
+      amount: 100,
+      currency: "USD",
+      name: "Coffee Shop",
+      entryable: Transaction.new
+    )
+
+    # Try to import a CSV with same date/amount but different name
+    import_csv = <<~CSV
+      date,name,amount
+      01/01/2024,Different Store,100
+    CSV
+
+    @import.update!(
+      account: account,
+      raw_file_str: import_csv,
+      date_col_label: "date",
+      amount_col_label: "amount",
+      name_col_label: "name",
+      date_format: "%m/%d/%Y",
+      amount_type_strategy: "signed_amount",
+      signage_convention: "inflows_negative"
+    )
+
+    @import.generate_rows_from_csv
+    @import.reload
+
+    # Should create a new entry because the name is different
+    assert_difference -> { Entry.count } => 1,
+                      -> { Transaction.count } => 1 do
+      @import.publish
+    end
+
+    # Both transactions should exist
+    assert_equal 2, account.entries.where(date: Date.new(2024, 1, 1), amount: 100).count
+  end
+
+  test "imports all identical transactions from CSV even when one exists in database" do
+    account = accounts(:depository)
+
+    # Create an existing manual transaction
+    existing_entry = account.entries.create!(
+      date: Date.new(2024, 1, 1),
+      amount: 50,
+      currency: "USD",
+      name: "Vending Machine",
+      entryable: Transaction.new
+    )
+
+    # Import CSV with 3 identical transactions (e.g., buying from vending machine 3 times)
+    import_csv = <<~CSV
+      date,name,amount
+      01/01/2024,Vending Machine,50
+      01/01/2024,Vending Machine,50
+      01/01/2024,Vending Machine,50
+    CSV
+
+    @import.update!(
+      account: account,
+      raw_file_str: import_csv,
+      date_col_label: "date",
+      amount_col_label: "amount",
+      name_col_label: "name",
+      date_format: "%m/%d/%Y",
+      amount_type_strategy: "signed_amount",
+      signage_convention: "inflows_negative"
+    )
+
+    @import.generate_rows_from_csv
+    @import.reload
+
+    # Should update 1 existing and create 2 new (total of 3 in system)
+    # The first matching row claims the existing entry, the other 2 create new ones
+    assert_difference -> { Entry.count } => 2,
+                      -> { Transaction.count } => 2 do
+      @import.publish
+    end
+
+    # Should have exactly 3 identical transactions total
+    assert_equal 3, account.entries.where(
+      date: Date.new(2024, 1, 1),
+      amount: 50,
+      name: "Vending Machine"
+    ).count
+
+    # The existing entry should be linked to the import
+    assert_equal @import.id, existing_entry.reload.import_id
+  end
+
+  test "imports all identical transactions from CSV when none exist in database" do
+    account = accounts(:depository)
+
+    # Import CSV with 3 identical transactions (no existing entry in database)
+    import_csv = <<~CSV
+      date,name,amount
+      01/01/2024,Vending Machine,50
+      01/01/2024,Vending Machine,50
+      01/01/2024,Vending Machine,50
+    CSV
+
+    @import.update!(
+      account: account,
+      raw_file_str: import_csv,
+      date_col_label: "date",
+      amount_col_label: "amount",
+      name_col_label: "name",
+      date_format: "%m/%d/%Y",
+      amount_type_strategy: "signed_amount",
+      signage_convention: "inflows_negative"
+    )
+
+    @import.generate_rows_from_csv
+    @import.reload
+
+    # Should create all 3 as new transactions
+    assert_difference -> { Entry.count } => 3,
+                      -> { Transaction.count } => 3 do
+      @import.publish
+    end
+
+    # Should have exactly 3 identical transactions
+    assert_equal 3, account.entries.where(
+      date: Date.new(2024, 1, 1),
+      amount: 50,
+      name: "Vending Machine"
+    ).count
+  end
+
+  test "does not raise error when all accounts are properly mapped" do
+    # Import CSV with multiple accounts, all mapped
+    import_csv = <<~CSV
+      date,name,amount,account
+      01/01/2024,Coffee Shop,100,Checking Account
+      01/02/2024,Grocery Store,200,Credit Card
+    CSV
+
+    checking = accounts(:depository)
+    credit_card = accounts(:credit_card)
+
+    @import.update!(
+      account: nil,
+      raw_file_str: import_csv,
+      date_col_label: "date",
+      amount_col_label: "amount",
+      name_col_label: "name",
+      account_col_label: "account",
+      date_format: "%m/%d/%Y",
+      amount_type_strategy: "signed_amount",
+      signage_convention: "inflows_negative"
+    )
+
+    @import.generate_rows_from_csv
+
+    # Map both accounts
+    @import.mappings.create!(key: "Checking Account", mappable: checking, type: "Import::AccountMapping")
+    @import.mappings.create!(key: "Credit Card", mappable: credit_card, type: "Import::AccountMapping")
+    @import.mappings.create!(key: "", mappable: nil, create_when_empty: false, type: "Import::CategoryMapping")
+    @import.mappings.create!(key: "", mappable: nil, create_when_empty: false, type: "Import::TagMapping")
+
+    @import.reload
+
+    # Should succeed without errors
+    assert_difference -> { Entry.count } => 2,
+                      -> { Transaction.count } => 2 do
+      @import.publish
+    end
+
+    assert_equal "complete", @import.status
+
+    # Check that each account got one entry from this import
+    assert_equal 1, checking.entries.where(import: @import).count
+    assert_equal 1, credit_card.entries.where(import: @import).count
+  end
 end