diff --git a/static/app/components/searchQueryBuilder/hooks/useQueryBuilderState.tsx b/static/app/components/searchQueryBuilder/hooks/useQueryBuilderState.tsx
index 549fc1e952fb..9191002ff351 100644
--- a/static/app/components/searchQueryBuilder/hooks/useQueryBuilderState.tsx
+++ b/static/app/components/searchQueryBuilder/hooks/useQueryBuilderState.tsx
@@ -205,6 +205,7 @@ type MultiSelectFilterValueAction = {
   token: TokenResult<Token.FILTER>;
   type: 'TOGGLE_FILTER_VALUE';
   value: string;
+  op?: TermOperator;
 };
 
 type UpdateAggregateArgsAction = {
@@ -693,7 +694,8 @@ export function modifyFilterValue(
 function updateFilterMultipleValues(
   state: QueryBuilderState,
   token: TokenResult<Token.FILTER>,
-  values: string[]
+  values: string[],
+  op?: TermOperator
 ) {
   // Deduplicate by canonical form while preserving the original text of the
   // first occurrence (so the query string keeps the user's original formatting)
@@ -712,7 +714,7 @@ function updateFilterMultipleValues(
     return true;
   });
   if (uniqNonEmptyValues.length === 0) {
-    return {...state, query: replaceQueryToken(state.query, token.value, '""')};
+    return {...state, query: modifyFilterValue(state.query, token, '""', op)};
   }
 
   const newValue =
@@ -720,7 +722,7 @@ function updateFilterMultipleValues(
       ? `[${uniqNonEmptyValues.join(',')}]`
       : uniqNonEmptyValues[0]!;
 
-  return {...state, query: replaceQueryToken(state.query, token.value, newValue)};
+  return {...state, query: modifyFilterValue(state.query, token, newValue, op)};
 }
 
 // Normalizes a filter value so that different surface representations of the
@@ -803,10 +805,12 @@ export function multiSelectTokenValue(
       );
 
       if (!containsValue) {
-        return updateFilterMultipleValues(state, action.token, [
-          ...values.map(({text}) => text),
-          action.value,
-        ]);
+        return updateFilterMultipleValues(
+          state,
+          action.token,
+          [...values.map(({text}) => text), action.value],
+          action.op
+        );
       }
 
       // The selected value was already present, so this is a deselect. Filter it
@@ -820,18 +824,18 @@ export function multiSelectTokenValue(
         }
       }
 
-      return updateFilterMultipleValues(state, action.token, newValues);
+      return updateFilterMultipleValues(state, action.token, newValues, action.op);
     }
     default: {
       // Single values use the same toggle semantics as lists: if the canonical
       // value is already selected, clear it; otherwise expand it into a list.
       if (canonicalizeSearchValue(tokenValue.value ?? '') === normalizedActionValue) {
-        return updateFilterMultipleValues(state, action.token, ['']);
+        return updateFilterMultipleValues(state, action.token, [''], action.op);
       }
       const newValue = tokenValue.value
         ? [tokenValue.text, action.value]
         : [action.value];
-      return updateFilterMultipleValues(state, action.token, newValue);
+      return updateFilterMultipleValues(state, action.token, newValue, action.op);
     }
   }
 }
diff --git a/static/app/components/searchQueryBuilder/index.spec.tsx b/static/app/components/searchQueryBuilder/index.spec.tsx
index 3f918deb5b2c..cdcfff190dd2 100644
--- a/static/app/components/searchQueryBuilder/index.spec.tsx
+++ b/static/app/components/searchQueryBuilder/index.spec.tsx
@@ -3831,6 +3831,26 @@ describe('SearchQueryBuilder', () => {
         expect(optionsAfterToggle).toEqual(initialOptions);
       });
 
+      it('switches from contains to is when selecting an initial value via checkbox', async () => {
+        render(
+          <SearchQueryBuilder
+            {...defaultProps}
+            initialQuery={`browser.name:${WildcardOperators.CONTAINS}""`}
+          />
+        );
+
+        await userEvent.click(
+          screen.getByRole('button', {name: 'Edit value for filter: browser.name'})
+        );
+        await userEvent.click(
+          await screen.findByRole('checkbox', {name: 'Toggle Chrome'})
+        );
+
+        expect(
+          await screen.findByRole('row', {name: 'browser.name:Chrome'})
+        ).toBeInTheDocument();
+      });
+
       it('does not reset frozen order when predefined sections rebuild', async () => {
         render(
           <SearchQueryBuilder
diff --git a/static/app/components/searchQueryBuilder/tokens/filter/valueCombobox.tsx b/static/app/components/searchQueryBuilder/tokens/filter/valueCombobox.tsx
index ae73d530b1ba..04654c57cc8c 100644
--- a/static/app/components/searchQueryBuilder/tokens/filter/valueCombobox.tsx
+++ b/static/app/components/searchQueryBuilder/tokens/filter/valueCombobox.tsx
@@ -588,6 +588,7 @@ function ItemCheckbox({disabled, value}: {disabled: boolean; value: string}) {
               type: 'TOGGLE_FILTER_VALUE',
               token,
               value: escapedValue,
+              op: getOperatorForSelectedValue(token),
             });
 
             const {selected: currentlySelected, selectedCount} = getMultiSelectValueState(
@@ -609,6 +610,20 @@ function ItemCheckbox({disabled, value}: {disabled: boolean; value: string}) {
   );
 }
 
+function getOperatorForSelectedValue(
+  token: TokenResult<Token.FILTER>
+): TermOperator | undefined {
+  if (
+    token.operator === TermOperator.CONTAINS &&
+    token.value.type === Token.VALUE_TEXT &&
+    !token.value.value
+  ) {
+    return token.negated ? TermOperator.NOT_EQUAL : TermOperator.DEFAULT;
+  }
+
+  return undefined;
+}
+
 function ValueComboboxCustomMenu(
   props: CustomComboboxMenuProps<SelectOptionWithKey<string>>
 ) {
@@ -1103,16 +1118,9 @@ export function SearchQueryBuilderValueCombobox({
       }
 
       // When selecting from dropdown with no existing value, switch from "contains" to "is"
-      let newOp: TermOperator | undefined;
-      if (
-        token.operator === TermOperator.CONTAINS &&
-        token.value.type === Token.VALUE_TEXT &&
-        !token.value.value
-      ) {
-        newOp = token.negated ? TermOperator.NOT_EQUAL : TermOperator.DEFAULT;
-      }
-
-      updateFilterValue(value, newOp, {escapeSearchValue: true});
+      updateFilterValue(value, getOperatorForSelectedValue(token), {
+        escapeSearchValue: true,
+      });
       trackAnalytics('search.value_autocompleted', {
         ...analyticsData,
         filter_value: value,
diff --git a/static/app/utils/fields/index.ts b/static/app/utils/fields/index.ts
index 8e7cbebf0fd1..a44288980577 100644
--- a/static/app/utils/fields/index.ts
+++ b/static/app/utils/fields/index.ts
@@ -2712,6 +2712,7 @@ const PREPROD_FIELD_DEFINITIONS: Record<string, FieldDefinition> = {
     desc: t('Status of the snapshot in the comparison pipeline'),
     kind: FieldKind.FIELD,
     valueType: FieldValueType.STRING,
+    allowWildcard: false,
     values: [
       'approved',
       'auto_approved',