diff --git a/specifyweb/backend/workbench/upload/column_options.py b/specifyweb/backend/workbench/upload/column_options.py
index 4a9bd278387..95b8f3fbb29 100644
--- a/specifyweb/backend/workbench/upload/column_options.py
+++ b/specifyweb/backend/workbench/upload/column_options.py
@@ -5,6 +5,7 @@
 from specifyweb.specify.utils.uiformatters import ScopedFormatter
 
 MatchBehavior = Literal["ignoreWhenBlank", "ignoreAlways", "ignoreNever"]
+DisambiguationBehavior = Literal["ask", "pickFirst"]
 
 # A single row in the workbench. Maps column names to values in the row
 Row = dict[str, str]
@@ -14,9 +15,10 @@ class ColumnOptions(NamedTuple):
     matchBehavior: MatchBehavior
     nullAllowed: bool
     default: str | None
+    disambiguationBehavior: DisambiguationBehavior
 
     def to_json(self) -> dict | str:
-        if self.matchBehavior == "ignoreNever" and self.nullAllowed and self.default is None:
+        if self.matchBehavior == "ignoreNever" and self.nullAllowed and self.default is None and self.disambiguationBehavior == "ask":
             return self.column
 
         return dict(self._asdict())
@@ -26,6 +28,7 @@ class ExtendedColumnOptions(NamedTuple):
     matchBehavior: MatchBehavior
     nullAllowed: bool
     default: str | None
+    disambiguationBehavior: DisambiguationBehavior
     uiformatter: ScopedFormatter | None
     schemaitem: Any
     picklist: Any
diff --git a/specifyweb/backend/workbench/upload/parsing.py b/specifyweb/backend/workbench/upload/parsing.py
index b59d6601d1c..7abcad0b1e3 100644
--- a/specifyweb/backend/workbench/upload/parsing.py
+++ b/specifyweb/backend/workbench/upload/parsing.py
@@ -5,7 +5,7 @@
 
 from specifyweb.specify.datamodel import datamodel
 from specifyweb.backend.workbench.upload.predicates import filter_match_key
-from .column_options import ExtendedColumnOptions
+from .column_options import DisambiguationBehavior, ExtendedColumnOptions
 from specifyweb.backend.workbench.upload.parse import parse_field, is_latlong, ParseSucess, ParseFailure
 
 Row = dict[str, str]
@@ -38,17 +38,20 @@ class ParseResult(NamedTuple):
     add_to_picklist: PicklistAddition | None
     column: str
     missing_required: str | None
+    disambiguation_behavior: DisambiguationBehavior
 
     @classmethod
-    def from_parse_success(cls, ps: ParseSucess, filter_on: Filter, add_to_picklist: PicklistAddition | None, column: str, missing_required: str | None):
-        return cls(filter_on=filter_on, upload=ps.payload, add_to_picklist=add_to_picklist, column=column, missing_required=missing_required)
+    def from_parse_success(cls, ps: ParseSucess, filter_on: Filter, add_to_picklist: PicklistAddition | None, column: str,
+                           missing_required: str | None, disambiguation_behavior: DisambiguationBehavior):
+        return cls(filter_on=filter_on, upload=ps.payload, add_to_picklist=add_to_picklist, column=column,
+                   missing_required=missing_required, disambiguation_behavior=disambiguation_behavior)
 
     def match_key(self) -> str:
         return filter_match_key(self.filter_on)
 
 
-def filter_and_upload(f: Filter, column: str) -> ParseResult:
-    return ParseResult(f, f, None, column, None)
+def filter_and_upload(f: Filter, column: str, disambiguation_behavior: DisambiguationBehavior = 'ask') -> ParseResult:
+    return ParseResult(f, f, None, column, None, disambiguation_behavior)
 
 
 def parse_many(tablename: str, mapping: dict[str, ExtendedColumnOptions], row: Row) -> tuple[list[ParseResult], list[WorkBenchParseFailure]]:
@@ -76,7 +79,7 @@ def parse_value(tablename: str, fieldname: str, value_in: str, colopts: Extended
                 None
             )
             result = ParseResult({fieldname: None}, {fieldname: None},
-                                 None, colopts.column, missing_required)
+                                 None, colopts.column, missing_required, colopts.disambiguationBehavior)
         else:
             result = _parse(tablename, fieldname,
                             colopts, colopts.default)
@@ -105,7 +108,7 @@ def _parse(tablename: str, fieldname: str, colopts: ExtendedColumnOptions, value
     field = table.get_field_strict(fieldname)
 
     if colopts.picklist:
-        result = parse_with_picklist(colopts.picklist, fieldname, value, colopts.column)
+        result = parse_with_picklist(colopts.picklist, fieldname, value, colopts.column, colopts.disambiguationBehavior,)
         if result is not None:
             if isinstance(result, ParseResult) and hasattr(field, 'length') and field.length is not None and len(result.upload[fieldname]) > field.length:
                 return WorkBenchParseFailure(
@@ -123,19 +126,19 @@ def _parse(tablename: str, fieldname: str, colopts: ExtendedColumnOptions, value
     if is_latlong(table, field) and isinstance(parsed, ParseSucess):
         coord_text_field = field.name.replace('itude', '') + 'text' if field.name else ''
         filter_on = {coord_text_field: parsed.payload[coord_text_field]}
-        return ParseResult.from_parse_success(parsed, filter_on, None, colopts.column, None)
+        return ParseResult.from_parse_success(parsed, filter_on, None, colopts.column, None, colopts.disambiguationBehavior)
 
     if isinstance(parsed, ParseFailure):
         return WorkBenchParseFailure.from_parse_failure(parsed, colopts.column)
     else:
-        return ParseResult.from_parse_success(parsed, parsed.payload, None, colopts.column, None)
+        return ParseResult.from_parse_success(parsed, parsed.payload, None, colopts.column, None, colopts.disambiguationBehavior)
 
 
-def parse_with_picklist(picklist, fieldname: str, value: str, column: str) -> ParseResult | WorkBenchParseFailure | None:
+def parse_with_picklist(picklist, fieldname: str, value: str, column: str, disambiguation_behavior: DisambiguationBehavior) -> ParseResult | WorkBenchParseFailure | None:
     if picklist.type == 0:  # items from picklistitems table
         try:
             item = picklist.picklistitems.get(title=value)
-            return filter_and_upload({fieldname: item.value}, column)
+            return filter_and_upload({fieldname: item.value}, column, disambiguation_behavior)
         except ObjectDoesNotExist:
             if picklist.readonly:
                 return WorkBenchParseFailure(
@@ -144,11 +147,11 @@ def parse_with_picklist(picklist, fieldname: str, value: str, column: str) -> Pa
                     column
                 )
             else:
-                return filter_and_upload({fieldname: value}, column)._replace(
+                return filter_and_upload({fieldname: value}, column, disambiguation_behavior)._replace(
                     add_to_picklist=PicklistAddition(
                         picklist=picklist, column=column, value=value)
                 )
-            return filter_and_upload({fieldname: value})
+            return filter_and_upload({fieldname: value}, column, disambiguation_behavior)
 
     elif picklist.type == 1:  # items from rows in some table
         # we ignore this type of picklist because it is primarily used to choose many-to-one's on forms
diff --git a/specifyweb/backend/workbench/upload/scoping.py b/specifyweb/backend/workbench/upload/scoping.py
index 24b7e887b11..f2d64ba7f34 100644
--- a/specifyweb/backend/workbench/upload/scoping.py
+++ b/specifyweb/backend/workbench/upload/scoping.py
@@ -147,6 +147,7 @@ def extend_columnoptions(
         matchBehavior=colopts.matchBehavior,
         nullAllowed=colopts.nullAllowed,
         default=colopts.default,
+        disambiguationBehavior=colopts.disambiguationBehavior,
         schemaitem=schemaitem,
         # Formatters are "scoped" here, that is, all they need is a value coming directly from the row.
         uiformatter=(None if scoped_formatter is None else CustomRepr(scoped_formatter, friendly_repr)),
diff --git a/specifyweb/backend/workbench/upload/tests/testparsing.py b/specifyweb/backend/workbench/upload/tests/testparsing.py
index 65867f44ea7..b68c50ae032 100644
--- a/specifyweb/backend/workbench/upload/tests/testparsing.py
+++ b/specifyweb/backend/workbench/upload/tests/testparsing.py
@@ -21,6 +21,7 @@
     WorkBenchParseFailure
 from ..upload_results_schema import schema as upload_results_schema
 from ..upload_table import UploadTable
+from specifyweb.specify import models
 
 from django.conf import settings
 
@@ -444,7 +445,7 @@ def test_tree_cols_with_ignoreWhenBlank(self) -> None:
             ranks=dict(
                 Genus=dict(name=parse_column_options('Genus')),
                 Species=dict(name=parse_column_options('Species'),
-                             author=ColumnOptions(column='Species Author', matchBehavior="ignoreWhenBlank", nullAllowed=True, default=None))
+                             author=ColumnOptions(column='Species Author', matchBehavior="ignoreWhenBlank", nullAllowed=True, default=None, disambiguationBehavior="ask"))
             )
         )
         data  = [
@@ -466,7 +467,7 @@ def test_higher_tree_cols_with_ignoreWhenBlank(self) -> None:
             ranks=dict(
                 Genus=dict(name=parse_column_options('Genus')),
                 Species=dict(name=parse_column_options('Species'),
-                             author=ColumnOptions(column='Species Author', matchBehavior="ignoreWhenBlank", nullAllowed=True, default=None)),
+                             author=ColumnOptions(column='Species Author', matchBehavior="ignoreWhenBlank", nullAllowed=True, default=None, disambiguationBehavior="ask")),
                 Subspecies=dict(name=parse_column_options('Subspecies')),
             )
         )
@@ -488,7 +489,7 @@ def test_tree_cols_with_ignoreNever(self) -> None:
             ranks=dict(
                 Genus=dict(name=parse_column_options('Genus')),
                 Species=dict(name=parse_column_options('Species'),
-                             author=ColumnOptions(column='Species Author', matchBehavior="ignoreNever", nullAllowed=True, default=None))
+                             author=ColumnOptions(column='Species Author', matchBehavior="ignoreNever", nullAllowed=True, default=None, disambiguationBehavior="ask"))
             )
         )
         data  = [
@@ -508,7 +509,7 @@ def test_tree_cols_with_required(self) -> None:
             ranks=dict(
                 Genus=dict(name=parse_column_options('Genus')),
                 Species=dict(name=parse_column_options('Species'),
-                             author=ColumnOptions(column='Species Author', matchBehavior="ignoreNever", nullAllowed=False, default=None))
+                             author=ColumnOptions(column='Species Author', matchBehavior="ignoreNever", nullAllowed=False, default=None, disambiguationBehavior="ask"))
             )
         )
         data  = [
@@ -530,7 +531,7 @@ def test_tree_cols_with_ignoreAlways(self) -> None:
             ranks=dict(
                 Genus=dict(name=parse_column_options('Genus')),
                 Species=dict(name=parse_column_options('Species'),
-                             author=ColumnOptions(column='Species Author', matchBehavior="ignoreAlways", nullAllowed=True, default=None))
+                             author=ColumnOptions(column='Species Author', matchBehavior="ignoreAlways", nullAllowed=True, default=None, disambiguationBehavior="ask"))
             )
         )
         data  = [
@@ -551,7 +552,7 @@ def test_wbcols_with_ignoreWhenBlank(self) -> None:
             name='Agent',
             wbcols={
                 'lastname': parse_column_options('lastname'),
-                'firstname': ColumnOptions(column='firstname', matchBehavior="ignoreWhenBlank", nullAllowed=True, default=None),
+                'firstname': ColumnOptions(column='firstname', matchBehavior="ignoreWhenBlank", nullAllowed=True, default=None, disambiguationBehavior="ask"),
             },
             overrideScope=None,
             static={},
@@ -577,7 +578,7 @@ def test_wbcols_with_ignoreWhenBlank_and_default(self) -> None:
             name='Agent',
             wbcols={
                 'lastname': parse_column_options('lastname'),
-                'firstname': ColumnOptions(column='firstname', matchBehavior="ignoreWhenBlank", nullAllowed=True, default="John"),
+                'firstname': ColumnOptions(column='firstname', matchBehavior="ignoreWhenBlank", nullAllowed=True, default="John", disambiguationBehavior="ask"),
             },
             overrideScope=None,
             static={},
@@ -609,7 +610,7 @@ def test_wbcols_with_ignoreNever(self) -> None:
             name='Agent',
             wbcols={
                 'lastname': parse_column_options('lastname'),
-                'firstname': ColumnOptions(column='firstname', matchBehavior="ignoreNever", nullAllowed=True, default=None),
+                'firstname': ColumnOptions(column='firstname', matchBehavior="ignoreNever", nullAllowed=True, default=None, disambiguationBehavior="ask"),
             },
             overrideScope=None,
             static={},
@@ -634,7 +635,7 @@ def test_wbcols_with_ignoreAlways(self) -> None:
             name='Agent',
             wbcols={
                 'lastname': parse_column_options('lastname'),
-                'firstname': ColumnOptions(column='firstname', matchBehavior="ignoreAlways", nullAllowed=True, default=None),
+                'firstname': ColumnOptions(column='firstname', matchBehavior="ignoreAlways", nullAllowed=True, default=None, disambiguationBehavior="ask"),
             },
             overrideScope=None,
             static={},
@@ -662,7 +663,7 @@ def test_wbcols_with_default(self) -> None:
             name='Agent',
             wbcols={
                 'lastname': parse_column_options('lastname'),
-                'firstname': ColumnOptions(column='firstname', matchBehavior="ignoreNever", nullAllowed=True, default="John"),
+                'firstname': ColumnOptions(column='firstname', matchBehavior="ignoreNever", nullAllowed=True, default="John", disambiguationBehavior="ask"),
             },
             overrideScope=None,
             static={},
@@ -690,7 +691,7 @@ def test_wbcols_with_default_matching(self) -> None:
             name='Agent',
             wbcols={
                 'lastname': parse_column_options('lastname'),
-                'firstname': ColumnOptions(column='firstname', matchBehavior="ignoreNever", nullAllowed=True, default="John"),
+                'firstname': ColumnOptions(column='firstname', matchBehavior="ignoreNever", nullAllowed=True, default="John", disambiguationBehavior="ask"),
             },
             overrideScope=None,
             static={},
@@ -721,7 +722,7 @@ def test_wbcols_with_default_and_null_disallowed(self) -> None:
             name='Agent',
             wbcols={
                 'lastname': parse_column_options('lastname'),
-                'firstname': ColumnOptions(column='firstname', matchBehavior="ignoreNever", nullAllowed=False, default="John"),
+                'firstname': ColumnOptions(column='firstname', matchBehavior="ignoreNever", nullAllowed=False, default="John", disambiguationBehavior="ask"),
             },
             overrideScope=None,
             static={},
@@ -750,7 +751,7 @@ def test_wbcols_with_default_blank(self) -> None:
             name='Agent',
             wbcols={
                 'lastname': parse_column_options('lastname'),
-                'firstname': ColumnOptions(column='firstname', matchBehavior="ignoreNever", nullAllowed=False, default=""),
+                'firstname': ColumnOptions(column='firstname', matchBehavior="ignoreNever", nullAllowed=False, default="", disambiguationBehavior="ask"),
             },
             overrideScope=None,
             static={},
@@ -780,7 +781,7 @@ def test_wbcols_with_null_disallowed(self) -> None:
             name='Agent',
             wbcols={
                 'lastname': parse_column_options('lastname'),
-                'firstname': ColumnOptions(column='firstname', matchBehavior="ignoreNever", nullAllowed=False, default=None),
+                'firstname': ColumnOptions(column='firstname', matchBehavior="ignoreNever", nullAllowed=False, default=None, disambiguationBehavior="ask"),
             },
             overrideScope=None,
             static={},
@@ -805,7 +806,7 @@ def test_wbcols_with_null_disallowed_and_ignoreWhenBlank(self) -> None:
             name='Agent',
             wbcols={
                 'lastname': parse_column_options('lastname'),
-                'firstname': ColumnOptions(column='firstname', matchBehavior="ignoreWhenBlank", nullAllowed=False, default=None),
+                'firstname': ColumnOptions(column='firstname', matchBehavior="ignoreWhenBlank", nullAllowed=False, default=None, disambiguationBehavior="ask"),
             },
             overrideScope=None,
             static={},
@@ -834,7 +835,7 @@ def test_wbcols_with_null_disallowed_and_ignoreAlways(self) -> None:
             name='Agent',
             wbcols={
                 'lastname': parse_column_options('lastname'),
-                'firstname': ColumnOptions(column='firstname', matchBehavior="ignoreAlways", nullAllowed=False, default=None),
+                'firstname': ColumnOptions(column='firstname', matchBehavior="ignoreAlways", nullAllowed=False, default=None, disambiguationBehavior="ask"),
             },
             overrideScope=None,
             static={},
@@ -857,3 +858,64 @@ def test_wbcols_with_null_disallowed_and_ignoreAlways(self) -> None:
         self.assertIsInstance(results[2].record_result, Uploaded)
         self.assertIsInstance(results[3].record_result, Matched)
         self.assertIsInstance(results[4].record_result, Matched)
+
+class DisambiguationBehaviorTests(UploadTestsBase):
+    def test_pickFirst_disambiguation_behavior(self) -> None:
+        # Upload some agents first
+        agent_plan = UploadTable(
+            name='Agent',
+            wbcols={
+                'firstname': parse_column_options('firstname'),
+                'lastname': parse_column_options('lastname'),
+                'email': parse_column_options('email'),
+            },
+            overrideScope=None,
+            static={},
+            toOne={},
+            toMany={}
+        )
+        agent_data = [
+            {'lastname': 'Doe', 'firstname': 'John', 'email': '0'},
+            {'lastname': 'Doe', 'firstname': 'John', 'email': '1'},
+        ]
+
+        results = do_upload(self.collection, agent_data, agent_plan, self.agent.id)
+        for result in results:
+            validate([result.to_json()], upload_results_schema, cls=Draft7Validator)
+
+        self.assertIsInstance(results[0].record_result, Uploaded)
+        self.assertIsInstance(results[1].record_result, Uploaded)
+        
+        # Try to add some Collection Objects with ambiguous catalogers
+        plan = UploadTable(
+            name='Collectionobject',
+            wbcols={
+                'catalognumber': parse_column_options('Cat #'),
+            },
+            overrideScope=None,
+            static={},
+            toOne={
+                'cataloger': UploadTable(
+                    name='Agent',
+                    wbcols={
+                        'lastname': parse_column_options('lastname'),
+                        'firstname': ColumnOptions(column='firstname', matchBehavior="ignoreNever", nullAllowed=True, default=None, disambiguationBehavior="pickFirst"),
+                    },
+                    overrideScope=None,
+                    static={},
+                    toOne={},
+                    toMany={},
+                )
+            },
+            toMany={}
+        )
+        data = [
+            {'Cat #': '124', 'lastname': 'Doe', 'firstname': 'John'},
+            {'Cat #': '125', 'lastname': 'Doe', 'firstname': 'Jane'}
+        ]
+        results = do_upload(self.collection, data, plan, self.agent.id)
+        for result in results:
+            validate([result.to_json()], upload_results_schema, cls=Draft7Validator)
+        
+        self.assertIsInstance(results[0].toOne['cataloger'].record_result, Matched, "Record was not disambiguated automatically despite having disambiguationBehavior='pickFirst'.")
+        self.assertIsInstance(results[1].toOne['cataloger'].record_result, Uploaded)
diff --git a/specifyweb/backend/workbench/upload/upload_attachments.py b/specifyweb/backend/workbench/upload/upload_attachments.py
index 410647cd0b0..b2d1527c5da 100644
--- a/specifyweb/backend/workbench/upload/upload_attachments.py
+++ b/specifyweb/backend/workbench/upload/upload_attachments.py
@@ -126,7 +126,8 @@ def add_attachments_to_plan(
                 column=f"_ATTACHMENT_ORDINAL_{index}",
                 matchBehavior="ignoreNever",
                 nullAllowed=True,
-                default="0"
+                default="0",
+                disambiguationBehavior="ask"
             )
             attackment_columns = {}
             for field in attachment_fields_to_copy:
@@ -134,7 +135,8 @@ def add_attachments_to_plan(
                     column=f"_ATTACHMENT_{field.upper()}_{index}",
                     matchBehavior="ignoreNever",
                     nullAllowed=True,
-                    default=attachment_field_default(field)
+                    default=attachment_field_default(field),
+                    disambiguationBehavior="ask"
                 )
             attachment_uploadable = UploadTable(
                 name="Attachment",
diff --git a/specifyweb/backend/workbench/upload/upload_plan_schema.py b/specifyweb/backend/workbench/upload/upload_plan_schema.py
index 3d35a7d0ae6..3cd7f748119 100644
--- a/specifyweb/backend/workbench/upload/upload_plan_schema.py
+++ b/specifyweb/backend/workbench/upload/upload_plan_schema.py
@@ -274,6 +274,12 @@
                     "default": None,
                     "description": "When set use this value for any cells that are empty in this column.",
                 },
+                "disambiguationBehavior": {
+                    "type": "string",
+                    "enum": ["ask", "pickFirst"],
+                    "default": "ask",
+                    "description": "How to disambiguate when multiple records are matched.",
+                },
             },
             "required": ["column"],
             "additionalProperties": False,
@@ -425,6 +431,7 @@ def parse_column_options(to_parse: str | dict) -> ColumnOptions:
             matchBehavior="ignoreNever",
             nullAllowed=True,
             default=None,
+            disambiguationBehavior="ask",
         )
     else:
         return ColumnOptions(
@@ -432,4 +439,5 @@ def parse_column_options(to_parse: str | dict) -> ColumnOptions:
             matchBehavior=to_parse.get("matchBehavior", "ignoreNever"),
             nullAllowed=to_parse.get("nullAllowed", True),
             default=to_parse.get("default", None),
+            disambiguationBehavior=to_parse.get("disambiguationBehavior", "ask")
         )
diff --git a/specifyweb/backend/workbench/upload/upload_table.py b/specifyweb/backend/workbench/upload/upload_table.py
index a5ab4cb3f9a..f0cc413ef80 100644
--- a/specifyweb/backend/workbench/upload/upload_table.py
+++ b/specifyweb/backend/workbench/upload/upload_table.py
@@ -674,12 +674,21 @@ def _match(
 
         n_matched = len(ids)
         if n_matched > 1:
+            if self._disambiguation_pick_first():
+                return Matched(id=ids[0], info=info)
             return MatchedMultiple(ids=ids, key=repr(cache_key), info=info)
         elif n_matched == 1:
             return Matched(id=ids[0], info=info)
         else:
             return None
 
+    def _disambiguation_pick_first(self) -> bool:
+        """Disambiguate by picking the first record if any field uses 'pickFirst'."""
+        for p in self.parsedFields:
+            if p.filter_on and p.disambiguation_behavior == "pickFirst":
+                return True
+        return False
+
     def _check_missing_required(self) -> ParseFailures | None:
         missing_requireds = [
             # TODO: there should probably be a different structure for
diff --git a/specifyweb/frontend/js_src/lib/components/WbPlanView/Mapper.tsx b/specifyweb/frontend/js_src/lib/components/WbPlanView/Mapper.tsx
index 6b7bb023457..c717e86a94b 100644
--- a/specifyweb/frontend/js_src/lib/components/WbPlanView/Mapper.tsx
+++ b/specifyweb/frontend/js_src/lib/components/WbPlanView/Mapper.tsx
@@ -651,6 +651,12 @@ export function Mapper(props: {
                         line,
                         defaultValue,
                       }),
+                    onChangeDisambiguationBehavior: (disambiguationBehavior) =>
+                      dispatch({
+                        type: 'ChangeDisambiguationBehaviorAction',
+                        line,
+                        disambiguationBehavior,
+                      }),
                   }),
                   previewOption: {
                     optionName: 'mappingOptions',
diff --git a/specifyweb/frontend/js_src/lib/components/WbPlanView/MapperComponents.tsx b/specifyweb/frontend/js_src/lib/components/WbPlanView/MapperComponents.tsx
index f8465cea9fa..ff9a781b052 100644
--- a/specifyweb/frontend/js_src/lib/components/WbPlanView/MapperComponents.tsx
+++ b/specifyweb/frontend/js_src/lib/components/WbPlanView/MapperComponents.tsx
@@ -32,7 +32,7 @@ import {
 } from './Mapper';
 import { getMappingLineData } from './navigator';
 import { navigatorSpecs } from './navigatorSpecs';
-import type { ColumnOptions, MatchBehaviors } from './uploadPlanParser';
+import type { ColumnOptions, DisambiguationBehaviors, MatchBehaviors } from './uploadPlanParser';
 
 export function MappingsControlPanel({
   showHiddenFields,
@@ -229,6 +229,7 @@ export function mappingOptionsMenu({
   onChangeMatchBehaviour: handleChangeMatchBehaviour,
   onToggleAllowNulls: handleToggleAllowNulls,
   onChangeDefaultValue: handleChangeDefaultValue,
+  onChangeDisambiguationBehavior: handleChangeDisambiguationBehavior,
 }: {
   readonly id: (suffix: string) => string;
   readonly isReadOnly: boolean;
@@ -236,6 +237,7 @@ export function mappingOptionsMenu({
   readonly onChangeMatchBehaviour: (matchBehavior: MatchBehaviors) => void;
   readonly onToggleAllowNulls: (allowNull: boolean) => void;
   readonly onChangeDefaultValue: (defaultValue: string | null) => void;
+  readonly onChangeDisambiguationBehavior: (disambiguationBehavior: DisambiguationBehaviors) => void;
 }): IR<MapperComponentData> {
   return {
     matchBehavior: {
@@ -318,6 +320,38 @@ export function mappingOptionsMenu({
       ),
       title: wbPlanText.defaultValueDescription(),
     },
+    disambiguationBehavior: {
+      optionLabel: (
+        <>
+          {wbPlanText.disambiguationBehavior()}
+          <Ul>
+            {Object.entries({
+              ask: {
+                title: wbPlanText.ask(),
+                description: wbPlanText.askDescription(),
+              },
+              pickFirst: {
+                title: wbPlanText.pickFirst(),
+                description: wbPlanText.pickFirstDescription(),
+              },
+            }).map(([id, { title, description }]) => (
+              <li key={id}>
+                <Label.Inline title={description}>
+                  <Input.Radio
+                    checked={columnOptions.disambiguationBehavior === id}
+                    isReadOnly={isReadOnly}
+                    name="disambiguation-behavior"
+                    value={id}
+                    onChange={(): void => handleChangeDisambiguationBehavior(id)}
+                  />
+                  {` ${title}`}
+                </Label.Inline>
+              </li>
+            ))}
+          </Ul>
+        </>
+      ),
+    },
   };
 }
 
diff --git a/specifyweb/frontend/js_src/lib/components/WbPlanView/__tests__/linesGetter.test.ts b/specifyweb/frontend/js_src/lib/components/WbPlanView/__tests__/linesGetter.test.ts
index 8d804e02644..c0c4bfec10e 100644
--- a/specifyweb/frontend/js_src/lib/components/WbPlanView/__tests__/linesGetter.test.ts
+++ b/specifyweb/frontend/js_src/lib/components/WbPlanView/__tests__/linesGetter.test.ts
@@ -47,6 +47,7 @@ theories(getLinesFromHeaders, [
           matchBehavior: 'ignoreNever',
           nullAllowed: true,
           default: null,
+          disambiguationBehavior: 'ask',
         },
       },
       /*
@@ -57,6 +58,7 @@ theories(getLinesFromHeaders, [
        *     matchBehavior: 'ignoreNever',
        *     nullAllowed: true,
        *     default: null,
+       *     disambiguationBehavior: 'ask,
        *   },
        * },
        * {
@@ -66,6 +68,7 @@ theories(getLinesFromHeaders, [
        *     matchBehavior: 'ignoreNever',
        *     nullAllowed: true,
        *     default: null,
+       *     disambiguationBehavior: 'ask,
        *   },
        * },
        * {
@@ -75,6 +78,7 @@ theories(getLinesFromHeaders, [
        *     matchBehavior: 'ignoreNever',
        *     nullAllowed: true,
        *     default: null,
+       *     disambiguationBehavior: 'ask,
        *   },
        * },
        * {
@@ -84,6 +88,7 @@ theories(getLinesFromHeaders, [
        *     matchBehavior: 'ignoreNever',
        *     nullAllowed: true,
        *     default: null,
+       *     disambiguationBehavior: 'ask,
        *   },
        * },
        * {
@@ -93,6 +98,7 @@ theories(getLinesFromHeaders, [
        *     matchBehavior: 'ignoreNever',
        *     nullAllowed: true,
        *     default: null,
+       *     disambiguationBehavior: 'ask,
        *   },
        * },
        * {
@@ -102,6 +108,7 @@ theories(getLinesFromHeaders, [
        *     matchBehavior: 'ignoreNever',
        *     nullAllowed: true,
        *     default: null,
+       *     disambiguationBehavior: 'ask,
        *   },
        * },
        * {
@@ -111,6 +118,7 @@ theories(getLinesFromHeaders, [
        *     matchBehavior: 'ignoreNever',
        *     nullAllowed: true,
        *     default: null,
+       *     disambiguationBehavior: 'ask,
        *   },
        * },
        * {
@@ -120,6 +128,7 @@ theories(getLinesFromHeaders, [
        *     matchBehavior: 'ignoreNever',
        *     nullAllowed: true,
        *     default: null,
+       *     disambiguationBehavior: 'ask,
        *   },
        * },
        * {
@@ -129,6 +138,7 @@ theories(getLinesFromHeaders, [
        *     matchBehavior: 'ignoreNever',
        *     nullAllowed: true,
        *     default: null,
+       *     disambiguationBehavior: 'ask,
        *   },
        * },
        */
@@ -161,6 +171,7 @@ theories(getLinesFromHeaders, [
           matchBehavior: 'ignoreNever',
           nullAllowed: true,
           default: null,
+          disambiguationBehavior: 'ask',
         },
       },
       {
@@ -170,6 +181,7 @@ theories(getLinesFromHeaders, [
           matchBehavior: 'ignoreNever',
           nullAllowed: true,
           default: null,
+          disambiguationBehavior: 'ask',
         },
       },
       {
@@ -179,6 +191,7 @@ theories(getLinesFromHeaders, [
           matchBehavior: 'ignoreNever',
           nullAllowed: true,
           default: null,
+          disambiguationBehavior: 'ask',
         },
       },
       {
@@ -188,6 +201,7 @@ theories(getLinesFromHeaders, [
           matchBehavior: 'ignoreNever',
           nullAllowed: true,
           default: null,
+          disambiguationBehavior: 'ask',
         },
       },
       {
@@ -197,6 +211,7 @@ theories(getLinesFromHeaders, [
           matchBehavior: 'ignoreNever',
           nullAllowed: true,
           default: null,
+          disambiguationBehavior: 'ask',
         },
       },
       {
@@ -206,6 +221,7 @@ theories(getLinesFromHeaders, [
           matchBehavior: 'ignoreNever',
           nullAllowed: true,
           default: null,
+          disambiguationBehavior: 'ask',
         },
       },
       {
@@ -215,6 +231,7 @@ theories(getLinesFromHeaders, [
           matchBehavior: 'ignoreNever',
           nullAllowed: true,
           default: null,
+          disambiguationBehavior: 'ask',
         },
       },
       {
@@ -224,6 +241,7 @@ theories(getLinesFromHeaders, [
           matchBehavior: 'ignoreNever',
           nullAllowed: true,
           default: null,
+          disambiguationBehavior: 'ask',
         },
       },
       {
@@ -233,6 +251,7 @@ theories(getLinesFromHeaders, [
           matchBehavior: 'ignoreNever',
           nullAllowed: true,
           default: null,
+          disambiguationBehavior: 'ask',
         },
       },
       {
@@ -242,6 +261,7 @@ theories(getLinesFromHeaders, [
           matchBehavior: 'ignoreNever',
           nullAllowed: true,
           default: null,
+          disambiguationBehavior: 'ask',
         },
       },
     ],
diff --git a/specifyweb/frontend/js_src/lib/components/WbPlanView/linesGetter.ts b/specifyweb/frontend/js_src/lib/components/WbPlanView/linesGetter.ts
index 41ff98b9aa2..3ad19a5752a 100644
--- a/specifyweb/frontend/js_src/lib/components/WbPlanView/linesGetter.ts
+++ b/specifyweb/frontend/js_src/lib/components/WbPlanView/linesGetter.ts
@@ -21,6 +21,7 @@ export const defaultColumnOptions: ColumnOptions = {
   matchBehavior: 'ignoreNever',
   nullAllowed: true,
   default: null,
+  disambiguationBehavior: 'ask',
 } as const;
 
 export const columnOptionsAreDefault = (
diff --git a/specifyweb/frontend/js_src/lib/components/WbPlanView/mappingReducer.ts b/specifyweb/frontend/js_src/lib/components/WbPlanView/mappingReducer.ts
index c59e2bccd55..a411082125a 100644
--- a/specifyweb/frontend/js_src/lib/components/WbPlanView/mappingReducer.ts
+++ b/specifyweb/frontend/js_src/lib/components/WbPlanView/mappingReducer.ts
@@ -27,8 +27,8 @@ import type {
   MappingState,
   SelectElementPosition,
 } from './Mapper';
-import { emptyMapping } from './mappingHelpers';
-import type { MatchBehaviors } from './uploadPlanParser';
+import { emptyMapping, mappingPathToString } from './mappingHelpers';
+import type { DisambiguationBehaviors, MatchBehaviors } from './uploadPlanParser';
 
 const modifyLine = (
   state: MappingState,
@@ -152,6 +152,14 @@ type ChangeDefaultValueAction = Action<
   }
 >;
 
+type ChangeDisambiguationBehaviorAction = Action<
+  'ChangeDisambiguationBehaviorAction',
+  {
+    readonly line: number;
+    readonly disambiguationBehavior: DisambiguationBehaviors;
+  }
+>;
+
 type UpdateLinesAction = Action<
   'UpdateLinesAction',
   { readonly lines: RA<MappingLine> }
@@ -178,6 +186,7 @@ export type MappingActions =
   | ChangeBatchEditPrefs
   | ChangeDefaultValueAction
   | ChangeMatchBehaviorAction
+  | ChangeDisambiguationBehaviorAction
   | ChangeSelectElementValueAction
   | ChangMustMatchPrefAction
   | ClearMappingLineAction
@@ -393,6 +402,23 @@ export const reducer = generateReducer<MappingState, MappingActions>({
     }),
     changesMade: true,
   }),
+  ChangeDisambiguationBehaviorAction: ({ state, action }) => {
+    const mappingPath = state.lines[action.line].mappingPath;
+    return {
+        ...state,
+        lines: state.lines.map((line) =>
+          isSameMappingPath(line.mappingPath, mappingPath) ?
+          {
+            ...line,
+            columnOptions: {
+              ...line.columnOptions,
+              disambiguationBehavior: action.disambiguationBehavior,
+            },
+          } : line
+        ),
+        changesMade: true,
+      }
+  },
   UpdateLinesAction: ({ state, action: { lines } }) => ({
     ...state,
     lines,
@@ -418,3 +444,6 @@ export const reducer = generateReducer<MappingState, MappingActions>({
     batchEditPrefs: action.prefs,
   }),
 });
+
+const isSameMappingPath = (pathA: MappingPath, pathB: MappingPath): boolean =>
+  mappingPathToString(pathA.slice(0, -1)) === mappingPathToString(pathB.slice(0, -1));
\ No newline at end of file
diff --git a/specifyweb/frontend/js_src/lib/components/WbPlanView/uploadPlanParser.ts b/specifyweb/frontend/js_src/lib/components/WbPlanView/uploadPlanParser.ts
index 21323955077..61528d9ae81 100644
--- a/specifyweb/frontend/js_src/lib/components/WbPlanView/uploadPlanParser.ts
+++ b/specifyweb/frontend/js_src/lib/components/WbPlanView/uploadPlanParser.ts
@@ -13,11 +13,13 @@ import { formatToManyIndex, formatTreeRank } from './mappingHelpers';
 import { RANK_KEY_DELIMITER } from './uploadPlanBuilder';
 
 export type MatchBehaviors = 'ignoreAlways' | 'ignoreNever' | 'ignoreWhenBlank';
+export type DisambiguationBehaviors = 'ask' | 'pickFirst'
 
 export type ColumnOptions = {
   readonly matchBehavior: MatchBehaviors;
   readonly nullAllowed: boolean;
   readonly default: string | null;
+  readonly disambiguationBehavior: DisambiguationBehaviors;
 };
 
 export type ColumnDefinition =
diff --git a/specifyweb/frontend/js_src/lib/localization/wbPlan.ts b/specifyweb/frontend/js_src/lib/localization/wbPlan.ts
index 31f57f98b8c..975e90a8d9d 100644
--- a/specifyweb/frontend/js_src/lib/localization/wbPlan.ts
+++ b/specifyweb/frontend/js_src/lib/localization/wbPlan.ts
@@ -770,4 +770,19 @@ export const wbPlanText = createDictionary({
       'O conjunto de dados selecionado não possui um plano de upload. Selecione outro.',
     'hr-hr': 'Odabrani skup podataka nema plan prijenosa. Odaberite drugi.',
   },
+  disambiguationBehavior: {
+    'en-us': 'Disambiguation Behavior:',
+  },
+  ask: {
+    'en-us': 'Ask',
+  },
+  askDescription: {
+    'en-us': 'You will be prompted to pick a record out of all the records matched to this field.',
+  },
+  pickFirst: {
+    'en-us': 'Pick first',
+  },
+  pickFirstDescription: {
+    'en-us': 'When multiple records are matched to this field, the first record will be picked automatically.',
+  }
 } as const);
diff --git a/specifyweb/frontend/js_src/lib/tests/fixtures/mappinglines.1.json b/specifyweb/frontend/js_src/lib/tests/fixtures/mappinglines.1.json
index 76d3c75cd21..9b1f292c3ba 100644
--- a/specifyweb/frontend/js_src/lib/tests/fixtures/mappinglines.1.json
+++ b/specifyweb/frontend/js_src/lib/tests/fixtures/mappinglines.1.json
@@ -7,7 +7,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreWhenBlank",
         "nullAllowed": true,
-        "default": "qwerty"
+        "default": "qwerty",
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -16,7 +17,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -25,7 +27,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -34,7 +37,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -43,7 +47,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -52,7 +57,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -61,7 +67,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -70,7 +77,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -79,7 +87,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -88,7 +97,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -97,7 +107,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -106,7 +117,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -121,7 +133,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -136,7 +149,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -151,7 +165,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -160,7 +175,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -175,7 +191,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -190,7 +207,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -205,7 +223,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -214,7 +233,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -229,7 +249,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -244,7 +265,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -259,7 +281,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -268,7 +291,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -283,7 +307,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -298,7 +323,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -313,7 +339,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -322,7 +349,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -337,7 +365,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -352,7 +381,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -367,7 +397,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -376,7 +407,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -391,7 +423,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -400,7 +433,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -409,7 +443,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -418,7 +453,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -427,7 +463,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreAlways",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -436,7 +473,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -445,7 +483,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -454,7 +493,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -463,7 +503,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -472,7 +513,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -481,7 +523,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -490,7 +533,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -499,7 +543,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -508,7 +553,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -517,7 +563,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -526,7 +573,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -535,7 +583,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -544,7 +593,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -553,7 +603,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     }
   ],
diff --git a/specifyweb/frontend/js_src/lib/tests/fixtures/uploadplan.1.json b/specifyweb/frontend/js_src/lib/tests/fixtures/uploadplan.1.json
index ea0336746b4..58caf26d7db 100644
--- a/specifyweb/frontend/js_src/lib/tests/fixtures/uploadplan.1.json
+++ b/specifyweb/frontend/js_src/lib/tests/fixtures/uploadplan.1.json
@@ -87,6 +87,7 @@
             "matchBehavior": "ignoreWhenBlank",
             "nullAllowed": true,
             "default": "qwerty",
+            "disambiguationBehavior": "ask",
             "column": "BMSM No."
           }
         },
@@ -286,6 +287,7 @@
                             "matchBehavior": "ignoreAlways",
                             "nullAllowed": true,
                             "default": null,
+                            "disambiguationBehavior": "ask",
                             "column": "Class"
                           }
                         }
diff --git a/specifyweb/frontend/js_src/lib/tests/fixtures/wbplanviewlines.1.json b/specifyweb/frontend/js_src/lib/tests/fixtures/wbplanviewlines.1.json
index e7149c8bb8d..5e13ff91de5 100644
--- a/specifyweb/frontend/js_src/lib/tests/fixtures/wbplanviewlines.1.json
+++ b/specifyweb/frontend/js_src/lib/tests/fixtures/wbplanviewlines.1.json
@@ -7,7 +7,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreWhenBlank",
         "nullAllowed": true,
-        "default": "qwerty"
+        "default": "qwerty",
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -16,7 +17,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreAlways",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -25,7 +27,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -34,7 +37,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -43,7 +47,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -52,7 +57,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -61,7 +67,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -70,7 +77,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -79,7 +87,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -88,7 +97,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -97,7 +107,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -106,7 +117,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -115,7 +127,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -124,7 +137,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -133,7 +147,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -142,7 +157,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -151,7 +167,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -160,7 +177,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -175,7 +193,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -190,7 +209,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -199,7 +219,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -208,7 +229,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -217,7 +239,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -232,7 +255,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -241,7 +265,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -250,7 +275,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -259,7 +285,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -268,7 +295,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -283,7 +311,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -292,7 +321,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -301,7 +331,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -310,7 +341,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -319,7 +351,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -328,7 +361,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -337,7 +371,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -346,7 +381,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -355,7 +391,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -364,7 +401,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -373,7 +411,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -382,7 +421,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -391,7 +431,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -400,7 +441,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -409,7 +451,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -418,7 +461,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -427,7 +471,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
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     {
@@ -436,7 +481,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
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     {
@@ -445,7 +491,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
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     {
@@ -454,7 +501,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -463,7 +511,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -472,7 +521,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
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     {
@@ -481,7 +531,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
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     {
@@ -490,7 +541,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
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     {
@@ -499,7 +551,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -508,7 +561,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
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     {
@@ -517,7 +571,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
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     {
@@ -526,7 +581,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
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     {
@@ -535,7 +591,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
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     {
@@ -544,7 +601,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -553,7 +611,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -562,7 +621,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -571,7 +631,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
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     {
@@ -580,7 +641,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -595,7 +657,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
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     {
@@ -610,7 +673,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -625,7 +689,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
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     {
@@ -634,7 +699,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
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     {
@@ -649,7 +715,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -664,7 +731,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -679,7 +747,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -688,7 +757,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -703,7 +773,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -718,7 +789,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -733,7 +805,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -742,7 +815,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -757,7 +831,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -772,7 +847,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     },
     {
@@ -787,7 +863,8 @@
       "columnOptions": {
         "matchBehavior": "ignoreNever",
         "nullAllowed": true,
-        "default": null
+        "default": null,
+        "disambiguationBehavior": "ask"
       }
     }
   ],