diff --git a/frontend/src/component/feature/FeatureStrategy/FeatureStrategyConstraints/AddSingleValueWidget.tsx b/frontend/src/component/feature/FeatureStrategy/FeatureStrategyConstraints/AddSingleValueWidget.tsx
index a6b1221bf2..545da27372 100644
--- a/frontend/src/component/feature/FeatureStrategy/FeatureStrategyConstraints/AddSingleValueWidget.tsx
+++ b/frontend/src/component/feature/FeatureStrategy/FeatureStrategyConstraints/AddSingleValueWidget.tsx
@@ -21,10 +21,11 @@ interface AddValuesProps {
     onAddValue: (newValue: string) => void;
     removeValue: () => void;
     currentValue?: string;
+    helpText?: string;
 }
 
 export const AddSingleValueWidget = forwardRef<HTMLDivElement, AddValuesProps>(
-    ({ currentValue, onAddValue, removeValue }, ref) => {
+    ({ currentValue, onAddValue, removeValue, helpText }, ref) => {
         const [open, setOpen] = useState(false);
         const positioningRef = useRef<HTMLDivElement>(null);
         useImperativeHandle(
@@ -56,6 +57,7 @@ export const AddSingleValueWidget = forwardRef<HTMLDivElement, AddValuesProps>(
                 <AddValuesPopover
                     initialValue={currentValue}
                     onAdd={handleAdd}
+                    helpText={helpText}
                     open={open}
                     anchorEl={positioningRef.current}
                     onClose={() => setOpen(false)}
diff --git a/frontend/src/component/feature/FeatureStrategy/FeatureStrategyConstraints/AddValuesPopover.tsx b/frontend/src/component/feature/FeatureStrategy/FeatureStrategyConstraints/AddValuesPopover.tsx
index 51a21e1ce4..c13d2bf25f 100644
--- a/frontend/src/component/feature/FeatureStrategy/FeatureStrategyConstraints/AddValuesPopover.tsx
+++ b/frontend/src/component/feature/FeatureStrategy/FeatureStrategyConstraints/AddValuesPopover.tsx
@@ -33,19 +33,31 @@ type AddValuesProps = {
     open: boolean;
     anchorEl: HTMLElement | null;
     onClose: () => void;
+    helpText?: string;
 };
 
+const HelpText = styled('p')(({ theme }) => ({
+    color: theme.palette.text.secondary,
+    fontSize: theme.typography.caption.fontSize,
+}));
+
+const AddButton = styled(Button)(({ theme }) => ({
+    minWidth: theme.spacing(4),
+}));
+
 export const AddValuesPopover: FC<AddValuesProps> = ({
     initialValue,
     onAdd,
     anchorEl,
     open,
     onClose,
+    helpText,
 }) => {
     const [inputValue, setInputValue] = useState(initialValue || '');
     const [error, setError] = useState('');
     const inputRef = useRef<HTMLInputElement>(null);
     const inputId = useId();
+    const helpTextId = useId();
 
     return (
         <StyledPopover
@@ -106,16 +118,19 @@ export const AddValuesPopover: FC<AddValuesProps> = ({
                         autoFocus
                         error={!!error}
                         helperText={error}
+                        aria-describedby={helpTextId}
                     />
-                    <Button
+                    <AddButton
                         variant='text'
                         type='submit'
+                        size='small'
                         color='primary'
                         disabled={!inputValue?.trim()}
                     >
                         Add
-                    </Button>
+                    </AddButton>
                 </InputRow>
+                <HelpText id={helpTextId}>{helpText}</HelpText>
             </form>
         </StyledPopover>
     );
diff --git a/frontend/src/component/feature/FeatureStrategy/FeatureStrategyConstraints/AddValuesWidget.tsx b/frontend/src/component/feature/FeatureStrategy/FeatureStrategyConstraints/AddValuesWidget.tsx
index 1d43370803..33b154cd65 100644
--- a/frontend/src/component/feature/FeatureStrategy/FeatureStrategyConstraints/AddValuesWidget.tsx
+++ b/frontend/src/component/feature/FeatureStrategy/FeatureStrategyConstraints/AddValuesWidget.tsx
@@ -28,10 +28,11 @@ const AddValuesButton = styled('button')(({ theme }) => ({
 
 interface AddValuesProps {
     onAddValues: (newValues: string[]) => void;
+    helpText?: string;
 }
 
 export const AddValuesWidget = forwardRef<HTMLButtonElement, AddValuesProps>(
-    ({ onAddValues }, ref) => {
+    ({ onAddValues, helpText }, ref) => {
         const [open, setOpen] = useState(false);
         const positioningRef = useRef<HTMLButtonElement>(null);
         useImperativeHandle(
@@ -73,6 +74,7 @@ export const AddValuesWidget = forwardRef<HTMLButtonElement, AddValuesProps>(
 
                 <AddValuesPopover
                     onAdd={handleAdd}
+                    helpText={helpText}
                     open={open}
                     anchorEl={positioningRef.current}
                     onClose={() => setOpen(false)}
diff --git a/frontend/src/component/feature/FeatureStrategy/FeatureStrategyConstraints/EditableConstraint.tsx b/frontend/src/component/feature/FeatureStrategy/FeatureStrategyConstraints/EditableConstraint.tsx
index d34c864915..100c411a51 100644
--- a/frontend/src/component/feature/FeatureStrategy/FeatureStrategyConstraints/EditableConstraint.tsx
+++ b/frontend/src/component/feature/FeatureStrategy/FeatureStrategyConstraints/EditableConstraint.tsx
@@ -146,21 +146,28 @@ const StyledCaseSensitiveIcon = styled(CaseSensitiveIcon)(({ theme }) => ({
     fill: 'currentcolor',
 }));
 
-const getInputType = (input: Input) => {
+type InputType =
+    | { input: 'legal values' }
+    | { input: 'date' }
+    | { input: 'single value'; type: 'number' | 'semver' }
+    | { input: 'multiple values' };
+
+const getInputType = (input: Input): InputType => {
     switch (input) {
         case 'IN_OPERATORS_LEGAL_VALUES':
         case 'STRING_OPERATORS_LEGAL_VALUES':
         case 'NUM_OPERATORS_LEGAL_VALUES':
         case 'SEMVER_OPERATORS_LEGAL_VALUES':
-            return 'legal values';
+            return { input: 'legal values' };
         case 'DATE_OPERATORS_SINGLE_VALUE':
-            return 'date input';
+            return { input: 'date' };
         case 'NUM_OPERATORS_SINGLE_VALUE':
+            return { input: 'single value', type: 'number' };
         case 'SEMVER_OPERATORS_SINGLE_VALUE':
-            return 'single text value';
+            return { input: 'single value', type: 'semver' };
         case 'IN_OPERATORS_FREETEXT':
         case 'STRING_OPERATORS_FREETEXT':
-            return 'free text';
+            return { input: 'multiple values' };
     }
 };
 
@@ -273,8 +280,8 @@ export const EditableConstraint: FC<Props> = ({
     };
 
     const TopRowInput = () => {
-        switch (inputType) {
-            case 'date input':
+        switch (inputType.input) {
+            case 'date':
                 return (
                     <ConstraintDateInput
                         setValue={setValue}
@@ -283,7 +290,7 @@ export const EditableConstraint: FC<Props> = ({
                         setError={setError}
                     />
                 );
-            case 'single text value':
+            case 'single value':
                 return (
                     <AddSingleValueWidget
                         onAddValue={(newValue) => {
@@ -291,11 +298,17 @@ export const EditableConstraint: FC<Props> = ({
                         }}
                         removeValue={() => setValue('')}
                         currentValue={localConstraint.value}
+                        helpText={
+                            inputType.type === 'number'
+                                ? 'Add a single number'
+                                : 'A semver value should be of the format X.Y.Z'
+                        }
                     />
                 );
-            case 'free text':
+            case 'multiple values':
                 return (
                     <AddValuesWidget
+                        helpText='Maximum 100 char length per value'
                         ref={addValuesButtonRef}
                         onAddValues={(newValues) => {
                             // todo (`addEditStrategy`): move deduplication logic higher up in the context handling
@@ -400,7 +413,7 @@ export const EditableConstraint: FC<Props> = ({
                     </StyledIconButton>
                 </HtmlTooltip>
             </TopRow>
-            {inputType === 'legal values' ? (
+            {inputType.input === 'legal values' ? (
                 <LegalValuesContainer>
                     <LegalValuesSelector
                         data={resolveLegalValues(
@@ -411,7 +424,7 @@ export const EditableConstraint: FC<Props> = ({
                         values={localConstraint.values || []}
                         setValuesWithRecord={setValuesWithRecord}
                         setValues={setValues}
-                    />{' '}
+                    />
                 </LegalValuesContainer>
             ) : null}
         </Container>