diff --git a/site/src/components/DurationField/DurationField.stories.tsx b/site/src/components/DurationField/DurationField.stories.tsx
index a68f3454ff..5ccb2dcb44 100644
--- a/site/src/components/DurationField/DurationField.stories.tsx
+++ b/site/src/components/DurationField/DurationField.stories.tsx
@@ -64,16 +64,27 @@ export const ChangeUnit: Story = {
 	},
 };
 
-export const CantConvertToDays: Story = {
+export const ConvertSmallHoursToDays: Story = {
 	args: {
-		valueMs: hoursToMs(2),
+		valueMs: hoursToMs(2), // 2 hours should convert to 1 day when switching units (rounded up)
 	},
 	play: async ({ canvasElement }) => {
 		const canvas = within(canvasElement);
+
+		// Initially should show 2 hours
+		const input = canvas.getByLabelText("Duration");
+		await expect(input).toHaveValue("2");
+
+		// Switch to days by clicking the dropdown
 		const unitDropdown = canvas.getByLabelText("Time unit");
 		await userEvent.click(unitDropdown);
+
+		// Find and click the Days option - this should now work (no longer disabled)
 		const daysOption = within(document.body).getByText("Days");
-		await expect(daysOption).toHaveAttribute("aria-disabled", "true");
+		await userEvent.click(daysOption);
+
+		// After switching to days, should show 1 day (2 hours rounded up to nearest day)
+		await expect(input).toHaveValue("1");
 	},
 };
 
diff --git a/site/src/components/DurationField/DurationField.tsx b/site/src/components/DurationField/DurationField.tsx
index 9f6a0fb543..9a2cb602fb 100644
--- a/site/src/components/DurationField/DurationField.tsx
+++ b/site/src/components/DurationField/DurationField.tsx
@@ -45,19 +45,12 @@ const reducer = (state: State, action: Action): State => {
 				state.unit,
 			);
 
-			if (
-				action.unit === "days" &&
-				!canConvertDurationToDays(currentDurationMs)
-			) {
-				return state;
-			}
-
 			return {
 				unit: action.unit,
 				durationFieldValue:
 					action.unit === "hours"
 						? durationInHours(currentDurationMs).toString()
-						: durationInDays(currentDurationMs).toString(),
+						: Math.ceil(durationInDays(currentDurationMs)).toString(),
 			};
 		}
 		default: {
@@ -124,17 +117,30 @@ export const DurationField: FC<DurationFieldProps> = (props) => {
 							type: "CHANGE_TIME_UNIT",
 							unit,
 						});
+
+						// Calculate the new duration in ms after changing the unit
+						// Important: When changing from hours to days, we need to round up to nearest day
+						// but keep the millisecond value consistent for the parent component
+						let newDurationMs: number;
+						if (unit === "hours") {
+							// When switching to hours, use the current milliseconds to get exact hours
+							newDurationMs = currentDurationMs;
+						} else {
+							// When switching to days, round up to the nearest day
+							const daysValue = Math.ceil(durationInDays(currentDurationMs));
+							newDurationMs = daysToDuration(daysValue);
+						}
+
+						// Notify parent component if the value has changed
+						if (newDurationMs !== parentValueMs) {
+							onChange(newDurationMs);
+						}
 					}}
 					inputProps={{ "aria-label": "Time unit" }}
 					IconComponent={ChevronDownIcon}
 				>
 					<MenuItem value="hours">Hours</MenuItem>
-					<MenuItem
-						value="days"
-						disabled={!canConvertDurationToDays(currentDurationMs)}
-					>
-						Days
-					</MenuItem>
+					<MenuItem value="days">Days</MenuItem>
 				</Select>
 			</div>
 
@@ -181,7 +187,3 @@ function hoursToDuration(hours: number): number {
 function daysToDuration(days: number): number {
 	return days * 24 * hoursToDuration(1);
 }
-
-function canConvertDurationToDays(duration: number): boolean {
-	return Number.isInteger(durationInDays(duration));
-}