diff --git a/app/controllers/import/configurations_controller.rb b/app/controllers/import/configurations_controller.rb
index f723c63efbb..535b2575167 100644
--- a/app/controllers/import/configurations_controller.rb
+++ b/app/controllers/import/configurations_controller.rb
@@ -38,6 +38,7 @@ def import_params
         :number_format,
         :signage_convention,
         :amount_type_strategy,
+        :amount_type_identifier_value,
         :amount_type_inflow_value,
       )
     end
diff --git a/app/javascript/controllers/import_controller.js b/app/javascript/controllers/import_controller.js
index 7c555d3ff50..9da24035f87 100644
--- a/app/javascript/controllers/import_controller.js
+++ b/app/javascript/controllers/import_controller.js
@@ -11,6 +11,7 @@ export default class extends Controller {
     "signedAmountFieldset",
     "customColumnFieldset",
     "amountTypeValue",
+    "amountTypeInflowValue",
     "amountTypeStrategySelect",
   ];
 
@@ -20,6 +21,9 @@ export default class extends Controller {
       this.amountTypeColumnKeyValue
     ) {
       this.#showAmountTypeValueTargets(this.amountTypeColumnKeyValue);
+      if (this.amountTypeValueTarget.querySelector("select")?.value) {
+        this.#showAmountTypeInflowValueTargets();
+      }
     }
   }
 
@@ -31,6 +35,9 @@ export default class extends Controller {
 
       if (this.amountTypeColumnKeyValue) {
         this.#showAmountTypeValueTargets(this.amountTypeColumnKeyValue);
+        if (this.amountTypeValueTarget.querySelector("select")?.value) {
+          this.#showAmountTypeInflowValueTargets();
+        }
       }
     }
 
@@ -45,6 +52,10 @@ export default class extends Controller {
     this.#showAmountTypeValueTargets(amountTypeColumnKey);
   }
 
+  handleAmountTypeIdentifierChange(event) {
+    this.#showAmountTypeInflowValueTargets();
+  }
+
   #showAmountTypeValueTargets(amountTypeColumnKey) {
     const selectableValues = this.#uniqueValuesForColumn(amountTypeColumnKey);
 
@@ -72,6 +83,29 @@ export default class extends Controller {
     select.appendChild(fragment);
   }
 
+  #showAmountTypeInflowValueTargets() {
+    // Called when amount_type_identifier_value changes
+    // Updates the displayed identifier value in the UI text and shows/hides the inflow value dropdown
+    const identifierValueSelect = this.amountTypeValueTarget.querySelector("select");
+    const selectedValue = identifierValueSelect.value;
+    
+    if (!selectedValue) {
+      this.amountTypeInflowValueTarget.classList.add("hidden");
+      this.amountTypeInflowValueTarget.classList.remove("flex");
+      return;
+    }
+
+    // Show the inflow value dropdown
+    this.amountTypeInflowValueTarget.classList.remove("hidden");
+    this.amountTypeInflowValueTarget.classList.add("flex");
+
+    // Update the displayed identifier value in the text
+    const identifierSpan = this.amountTypeInflowValueTarget.querySelector("span.font-medium");
+    if (identifierSpan) {
+      identifierSpan.textContent = selectedValue;
+    }
+  }
+
   #uniqueValuesForColumn(column) {
     const colIdx = this.csvValue[0].indexOf(column);
     const values = this.csvValue.slice(1).map((row) => row[colIdx]);
@@ -101,6 +135,12 @@ export default class extends Controller {
     this.customColumnFieldsetTarget.classList.add("hidden");
     this.signedAmountFieldsetTarget.classList.remove("hidden");
 
+    // Hide the inflow value targets when using signed amount strategy
+    this.amountTypeValueTarget.classList.add("hidden");
+    this.amountTypeValueTarget.classList.remove("flex");
+    this.amountTypeInflowValueTarget.classList.add("hidden");
+    this.amountTypeInflowValueTarget.classList.remove("flex");
+
     // Remove required from custom column fields
     this.customColumnFieldsetTarget
       .querySelectorAll("select, input")
diff --git a/app/models/import.rb b/app/models/import.rb
index 5d6bea64796..28e0bb2f588 100644
--- a/app/models/import.rb
+++ b/app/models/import.rb
@@ -35,6 +35,7 @@ class Import < ApplicationRecord
   validates :col_sep, inclusion: { in: SEPARATORS.map(&:last) }
   validates :signage_convention, inclusion: { in: SIGNAGE_CONVENTIONS }, allow_nil: true
   validates :number_format, presence: true, inclusion: { in: NUMBER_FORMATS.keys }
+  validate :custom_column_import_requires_identifier
 
   has_many :rows, dependent: :destroy
   has_many :mappings, dependent: :destroy
@@ -287,4 +288,11 @@ def sanitize_number(value)
     def set_default_number_format
       self.number_format ||= "1,234.56" # Default to US/UK format
     end
+
+    def custom_column_import_requires_identifier
+      return unless amount_type_strategy == "custom_column"
+      return if amount_type_identifier_value.present? || amount_type_inflow_value.present?
+
+      errors.add(:base, "Custom column imports require either an identifier value or a legacy inflow indicator")
+    end
 end
diff --git a/app/models/import/row.rb b/app/models/import/row.rb
index ef16d26e551..8e9b6dc9f9d 100644
--- a/app/models/import/row.rb
+++ b/app/models/import/row.rb
@@ -47,12 +47,25 @@ def apply_transaction_signage_convention(value)
       if import.amount_type_strategy == "signed_amount"
         value * (import.signage_convention == "inflows_positive" ? -1 : 1)
       elsif import.amount_type_strategy == "custom_column"
-        inflow_value = import.amount_type_inflow_value
-
-        if entity_type == inflow_value
-          value * -1
+        legacy_identifier = import.amount_type_inflow_value
+        selected_identifier =
+          if import.amount_type_identifier_value.present?
+            import.amount_type_identifier_value
+          else
+            legacy_identifier
+          end
+
+        inflow_treatment =
+          if import.amount_type_inflow_value.in?(%w[inflows_positive inflows_negative])
+            import.amount_type_inflow_value
+          else
+            "inflows_positive"
+          end
+
+        if entity_type == selected_identifier
+          value * (inflow_treatment == "inflows_positive" ? -1 : 1)
         else
-          value
+          value * (inflow_treatment == "inflows_positive" ? 1 : -1)
         end
       else
         raise "Unknown amount type strategy for import: #{import.amount_type_strategy}"
diff --git a/app/views/import/configurations/_transaction_import.html.erb b/app/views/import/configurations/_transaction_import.html.erb
index 84301d6910e..7a391892640 100644
--- a/app/views/import/configurations/_transaction_import.html.erb
+++ b/app/views/import/configurations/_transaction_import.html.erb
@@ -78,11 +78,21 @@
       <div class="items-center gap-2 text-sm <%= @import.entity_type_col_label.nil? ? "hidden" : "flex" %>" data-import-target="amountTypeValue">
         <span class="shrink-0 text-secondary">↪</span>
         <span class="text-secondary">Set</span>
-        <%= form.select :amount_type_inflow_value,
+        <%= form.select :amount_type_identifier_value,
                         @import.selectable_amount_type_values,
-                        { prompt: "Select column", container_class: "w-48 px-3 py-1.5 border border-secondary rounded-md" },
+                        { prompt: "Select value", container_class: "w-48 px-3 py-1.5 border border-secondary rounded-md" },
+                        required: @import.amount_type_strategy == "custom_column",
+                        data: { action: "import#handleAmountTypeIdentifierChange" } %>
+        <span class="text-secondary">as identifier value</span>
+      </div>
+
+      <div class="items-center gap-2 text-sm <%= @import.amount_type_identifier_value.nil? ? "hidden" : "flex" %>" data-import-target="amountTypeInflowValue">
+        <span class="shrink-0 text-secondary">↪</span>
+        <span class="text-secondary">Treat "<span class="font-medium"><%= @import.amount_type_identifier_value %></span>" as</span>
+        <%= form.select :amount_type_inflow_value,
+                        [["Income (inflow)", "inflows_positive"], ["Expense (outflow)", "inflows_negative"]],
+                        { prompt: "Select type", container_class: "w-48 px-3 py-1.5 border border-secondary rounded-md" },
                         required: @import.amount_type_strategy == "custom_column" %>
-        <span class="text-secondary">as "income" (inflow) value</span>
       </div>
     </div>
   <% end %>
diff --git a/db/migrate/20251002120000_add_amount_type_identifier_value_to_imports.rb b/db/migrate/20251002120000_add_amount_type_identifier_value_to_imports.rb
new file mode 100644
index 00000000000..bb910fdf2aa
--- /dev/null
+++ b/db/migrate/20251002120000_add_amount_type_identifier_value_to_imports.rb
@@ -0,0 +1,5 @@
+class AddAmountTypeIdentifierValueToImports < ActiveRecord::Migration[7.2]
+  def change
+    add_column :imports, :amount_type_identifier_value, :string
+  end
+end
diff --git a/test/models/transaction_import_test.rb b/test/models/transaction_import_test.rb
index dc94b20cfeb..25de8237589 100644
--- a/test/models/transaction_import_test.rb
+++ b/test/models/transaction_import_test.rb
@@ -84,7 +84,8 @@ class TransactionImportTest < ActiveSupport::TestCase
       date_format: "%m/%d/%Y",
       amount_col_label: "amount",
       entity_type_col_label: "amount_type",
-      amount_type_inflow_value: "debit",
+      amount_type_identifier_value: "debit",
+      amount_type_inflow_value: "inflows_positive",
       amount_type_strategy: "custom_column",
       signage_convention: nil # Explicitly set to nil to prove this is not needed
     )