diff --git a/desktop/src/features/workflows/ui/WorkflowConditionBuilder.tsx b/desktop/src/features/workflows/ui/WorkflowConditionBuilder.tsx
index 8d20c26e05..aba54ecb8c 100644
--- a/desktop/src/features/workflows/ui/WorkflowConditionBuilder.tsx
+++ b/desktop/src/features/workflows/ui/WorkflowConditionBuilder.tsx
@@ -84,7 +84,7 @@ export function WorkflowConditionBuilder({
   channels,
   disabled,
   idPrefix,
-  matchAllHint = "Leave empty to match every event.",
+  matchAllLabel = "All events",
   onChange,
   triggerType,
   value,
@@ -92,7 +92,7 @@ export function WorkflowConditionBuilder({
   channels: Channel[];
   disabled?: boolean;
   idPrefix: string;
-  matchAllHint?: string;
+  matchAllLabel?: string;
   onChange: (value: string) => void;
   triggerType: TriggerType;
   value: string;
@@ -164,23 +164,26 @@ export function WorkflowConditionBuilder({
     )
     .join(", ");
   const fieldOptions = [
+    { label: matchAllLabel, value: "" },
     ...fields,
     { label: "Custom", value: CUSTOM_CONDITION_FIELD },
   ];
 
   return (
     <div className="space-y-3">
-      <fieldset className="space-y-1.5">
-        <legend className="text-xs font-medium text-muted-foreground">
-          Condition (optional)
-        </legend>
+      <fieldset>
+        <legend className="sr-only">Condition</legend>
         <div className="grid grid-cols-2 gap-2.5">
           {fieldOptions.map((field) => {
+            const isMatchAll = field.value === "";
             const isCustom = field.value === CUSTOM_CONDITION_FIELD;
             const isSelected = editor.field === field.value;
             return (
               <div
-                className={cn("relative", isCustom && "col-span-2")}
+                className={cn(
+                  "relative",
+                  (isMatchAll || isCustom) && "col-span-2",
+                )}
                 key={field.value}
               >
                 <button
@@ -196,7 +199,8 @@ export function WorkflowConditionBuilder({
                   )}
                   disabled={disabled}
                   onClick={() => {
-                    if (isSelected) {
+                    if (isSelected) return;
+                    if (isMatchAll) {
                       setEditor({
                         field: "",
                         operator: "contains",
@@ -358,8 +362,6 @@ export function WorkflowConditionBuilder({
           ) : null}
         </>
       ) : null}
-
-      <p className="text-xs text-muted-foreground">{matchAllHint}</p>
     </div>
   );
 }
diff --git a/desktop/src/features/workflows/ui/WorkflowFormBuilder.tsx b/desktop/src/features/workflows/ui/WorkflowFormBuilder.tsx
index 5bbf98bade..83c8861a36 100644
--- a/desktop/src/features/workflows/ui/WorkflowFormBuilder.tsx
+++ b/desktop/src/features/workflows/ui/WorkflowFormBuilder.tsx
@@ -67,7 +67,9 @@ function TriggerConfigFields({
             channels={channels}
             disabled={disabled}
             idPrefix="wf-trigger-filter"
-            matchAllHint="Leave empty to trigger on every message."
+            matchAllLabel={
+              trigger.on === "message_posted" ? "All messages" : "All diffs"
+            }
             onChange={(filter) => onUpdate({ ...trigger, filter })}
             triggerType={trigger.on}
             value={trigger.filter ?? ""}
diff --git a/desktop/src/features/workflows/ui/WorkflowScheduleFields.tsx b/desktop/src/features/workflows/ui/WorkflowScheduleFields.tsx
index 8bb0db807f..d52612f339 100644
--- a/desktop/src/features/workflows/ui/WorkflowScheduleFields.tsx
+++ b/desktop/src/features/workflows/ui/WorkflowScheduleFields.tsx
@@ -78,20 +78,9 @@ export function WorkflowScheduleFields({
 
   return (
     <div className="space-y-3">
-      <div className="space-y-1.5">
-        <div className="flex items-center justify-between gap-3">
-          <p
-            className="text-xs font-medium text-muted-foreground"
-            id="wf-trigger-frequency-label"
-          >
-            Repeats
-          </p>
-        </div>
-        <div
-          aria-labelledby="wf-trigger-frequency-label"
-          className="grid grid-cols-2 gap-2.5"
-          role="radiogroup"
-        >
+      <fieldset>
+        <legend className="sr-only">Repeats</legend>
+        <div className="grid grid-cols-2 gap-2.5">
           {SCHEDULE_FREQUENCIES.map((frequency) => {
             const id = `wf-trigger-frequency-${frequency}`;
             return (
@@ -139,7 +128,7 @@ export function WorkflowScheduleFields({
             );
           })}
         </div>
-      </div>
+      </fieldset>
 
       {schedule.frequency === "weekly" ? (
         <fieldset className="space-y-1.5">
diff --git a/desktop/src/features/workflows/ui/WorkflowStepCard.tsx b/desktop/src/features/workflows/ui/WorkflowStepCard.tsx
index 3e900be4d6..54584e0020 100644
--- a/desktop/src/features/workflows/ui/WorkflowStepCard.tsx
+++ b/desktop/src/features/workflows/ui/WorkflowStepCard.tsx
@@ -386,7 +386,7 @@ export function WorkflowStepCard({
             channels={channels}
             disabled={disabled}
             idPrefix={`${prefix}-condition`}
-            matchAllHint="Leave empty to run this step every time the workflow starts."
+            matchAllLabel="Every run"
             onChange={(condition) => onUpdate({ ...step, condition })}
             triggerType={triggerType}
             value={step.condition ?? ""}
diff --git a/desktop/tests/e2e/workflows.spec.ts b/desktop/tests/e2e/workflows.spec.ts
index c92ae7d31c..158d431a8b 100644
--- a/desktop/tests/e2e/workflows.spec.ts
+++ b/desktop/tests/e2e/workflows.spec.ts
@@ -130,7 +130,7 @@ async function createWorkflow(
   }
   if (options?.stepCondition) {
     await dialog
-      .getByRole("group", { name: "Condition (optional)" })
+      .getByRole("group", { name: "Condition" })
       .getByRole("button", { name: "Custom" })
       .click();
     await dialog.getByLabel("Custom expression").fill(options.stepCondition);
@@ -275,11 +275,15 @@ test("builds a valid trigger condition from plain-language choices", async ({
   await dialog.getByRole("button", { name: /^Trigger:/ }).click();
   const inspector = dialog.getByTestId("workflow-node-inspector");
 
-  const conditionFields = inspector.getByRole("group", {
-    name: "Condition (optional)",
-  });
+  const conditionFields = inspector.getByRole("group", { name: "Condition" });
   const conditionOptions = conditionFields.getByRole("button");
-  await expect(conditionOptions).toHaveCount(5);
+  await expect(conditionOptions).toHaveCount(6);
+  const allMessages = conditionFields.getByRole("button", {
+    name: "All messages",
+  });
+  await expect(allMessages).toHaveAttribute("aria-pressed", "true");
+  await allMessages.click();
+  await expect(allMessages).toHaveAttribute("aria-pressed", "true");
   await expect(
     conditionFields.getByRole("button", { name: "Message text" }),
   ).toHaveAttribute("aria-pressed", "false");
@@ -288,6 +292,7 @@ test("builds a valid trigger condition from plain-language choices", async ({
   }
 
   await conditionFields.getByRole("button", { name: "Message text" }).click();
+  await expect(allMessages).toHaveAttribute("aria-pressed", "false");
   await inspector.getByLabel("Text to match").fill('deploy "buzz"');
   await dialog.getByRole("tab", { name: "YAML" }).click();
   await expect(dialog.getByLabel("Workflow YAML")).toHaveValue(
@@ -297,7 +302,7 @@ test("builds a valid trigger condition from plain-language choices", async ({
   await dialog.getByRole("tab", { name: "Form" }).click();
   await dialog.getByRole("button", { name: /^Trigger:/ }).click();
   const roundTrippedFields = inspector.getByRole("group", {
-    name: "Condition (optional)",
+    name: "Condition",
   });
   await expect(
     roundTrippedFields.getByRole("button", { name: "Message text" }),
@@ -311,6 +316,11 @@ test("builds a valid trigger condition from plain-language choices", async ({
   );
   await expect(inspector.getByText(/Use an evalexpr expression/)).toBeVisible();
   await customCondition.click();
+  await expect(customCondition).toHaveAttribute("aria-pressed", "true");
+  await expect(inspector.getByLabel("Custom expression")).toBeVisible();
+  await roundTrippedFields
+    .getByRole("button", { name: "All messages" })
+    .click();
   await expect(customCondition).toHaveAttribute("aria-pressed", "false");
   await expect(inspector.getByLabel("Custom expression")).not.toBeVisible();
 });