diff --git a/e2e/__screenshots__/work-orders/work-orders.visual.spec.ts/wo-detail.png b/e2e/__screenshots__/work-orders/work-orders.visual.spec.ts/wo-detail.png
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diff --git a/e2e/__screenshots__/work-orders/work-orders.visual.spec.ts/wo-error.png b/e2e/__screenshots__/work-orders/work-orders.visual.spec.ts/wo-error.png
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diff --git a/e2e/__screenshots__/work-orders/work-orders.visual.spec.ts/wo-filters.png b/e2e/__screenshots__/work-orders/work-orders.visual.spec.ts/wo-filters.png
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diff --git a/e2e/__screenshots__/work-orders/work-orders.visual.spec.ts/wo-list.png b/e2e/__screenshots__/work-orders/work-orders.visual.spec.ts/wo-list.png
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diff --git a/e2e/__screenshots__/work-orders/work-orders.visual.spec.ts/wo-new.png b/e2e/__screenshots__/work-orders/work-orders.visual.spec.ts/wo-new.png
index 0c225e74..13e7ffe3 100644
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diff --git a/src/app/(protected)/workorders/_components/list/table/wo-table-head.tsx b/src/app/(protected)/workorders/_components/list/table/wo-table-head.tsx
index c490f17e..14a446fd 100644
--- a/src/app/(protected)/workorders/_components/list/table/wo-table-head.tsx
+++ b/src/app/(protected)/workorders/_components/list/table/wo-table-head.tsx
@@ -1,4 +1,5 @@
 import { WO_TABLE_COLS } from "./wo-table-cols";
+import { WoTableHeaderLabel } from "./wo-table-header-label";
 
 export function WoTableHead() {
   return (
@@ -25,7 +26,7 @@ export function WoTableHead() {
                 borderBottom: "1px solid var(--border)",
               }}
             >
-              {col.label}
+              <WoTableHeaderLabel colKey={col.key} label={col.label} />
               {Boolean(srLabel) && <span className="sr-only">{srLabel}</span>}
             </th>
           );
diff --git a/src/app/(protected)/workorders/_components/list/table/wo-table-header-label.tsx b/src/app/(protected)/workorders/_components/list/table/wo-table-header-label.tsx
new file mode 100644
index 00000000..1902b463
--- /dev/null
+++ b/src/app/(protected)/workorders/_components/list/table/wo-table-header-label.tsx
@@ -0,0 +1,39 @@
+import { Tooltip } from "@mui/material";
+import { CircleQuestionMark } from "lucide-react";
+
+import { getWoTableHeaderTooltip } from "@/domain/work-orders/constants/wo-table-header-tooltips";
+
+type WoTableHeaderLabelProps = {
+  colKey: string;
+  label: string;
+};
+
+export function WoTableHeaderLabel({ colKey, label }: WoTableHeaderLabelProps) {
+  const tooltip = getWoTableHeaderTooltip(colKey);
+
+  if (!tooltip) {
+    return <>{label}</>;
+  }
+
+  return (
+    <span style={{ display: "inline-flex", alignItems: "center", gap: 4 }}>
+      {label}
+      <Tooltip title={tooltip} arrow placement="top">
+        <button
+          type="button"
+          aria-label={`${label} column help`}
+          style={{
+            display: "inline-flex",
+            cursor: "help",
+            color: "var(--color-text-muted)",
+            padding: 0,
+            border: 0,
+            background: "transparent",
+          }}
+        >
+          <CircleQuestionMark size={13} aria-hidden="true" />
+        </button>
+      </Tooltip>
+    </span>
+  );
+}
diff --git a/src/domain/work-orders/constants/wo-table-header-tooltips.ts b/src/domain/work-orders/constants/wo-table-header-tooltips.ts
new file mode 100644
index 00000000..24ff23be
--- /dev/null
+++ b/src/domain/work-orders/constants/wo-table-header-tooltips.ts
@@ -0,0 +1,17 @@
+/**
+ * Help copy for date-column headers on the work orders board table.
+ * Keyed by the `WO_TABLE_COLS` column key; only columns with copy here show a
+ * header help icon. `appt` (Appt Time) is an intentional open point — do not
+ * add it without a business-rule decision.
+ */
+export const WO_TABLE_HEADER_TOOLTIPS = {
+  sched: "The date the work is planned to happen. Setting it moves the work order to Scheduled.",
+  due: "The deadline for the work — when it must be completed by.",
+  completed: "The date the vendor actually finished the work. Required to complete the work order.",
+} as const;
+
+export function getWoTableHeaderTooltip(colKey: string): string | undefined {
+  return colKey in WO_TABLE_HEADER_TOOLTIPS
+    ? WO_TABLE_HEADER_TOOLTIPS[colKey as keyof typeof WO_TABLE_HEADER_TOOLTIPS]
+    : undefined;
+}
diff --git a/src/test/app/(protected)/workorders/wo-table-head-date-tooltips.test.tsx b/src/test/app/(protected)/workorders/wo-table-head-date-tooltips.test.tsx
new file mode 100644
index 00000000..a25bd953
--- /dev/null
+++ b/src/test/app/(protected)/workorders/wo-table-head-date-tooltips.test.tsx
@@ -0,0 +1,71 @@
+import { screen, within } from "@testing-library/react";
+import userEvent from "@testing-library/user-event";
+import { describe, expect, it } from "vitest";
+
+import { WoTableHead } from "@/app/(protected)/workorders/_components/list/table/wo-table-head";
+import { getWoTableHeaderTooltip } from "@/domain/work-orders/constants/wo-table-header-tooltips";
+import { renderWithProviders } from "@/test/test-utils";
+
+const CASES = [
+  {
+    columnName: "SCHEDULE ON",
+    tooltip:
+      "The date the work is planned to happen. Setting it moves the work order to Scheduled.",
+  },
+  {
+    columnName: "DUE DATE",
+    tooltip: "The deadline for the work — when it must be completed by.",
+  },
+  {
+    columnName: "COMPLETED DATE",
+    tooltip: "The date the vendor actually finished the work. Required to complete the work order.",
+  },
+];
+
+function renderHead() {
+  return renderWithProviders(
+    <table>
+      <WoTableHead />
+    </table>,
+    { withAuth: false },
+  );
+}
+
+describe("WoTableHead date column header tooltips (SH-195)", () => {
+  it.each(CASES)(
+    "shows the $columnName help icon and tooltip copy on hover",
+    async ({ columnName, tooltip }) => {
+      const user = userEvent.setup();
+      renderHead();
+
+      const header = screen.getByRole("columnheader", { name: new RegExp(`^${columnName}`) });
+      const icon = within(header).getByRole("button", { name: `${columnName} column help` });
+
+      await user.hover(icon);
+
+      const tip = await screen.findByText(tooltip);
+      expect(tip).toBeInTheDocument();
+    },
+    15000,
+  );
+
+  it("moves focus to the help icon on tab and keeps it keyboard reachable", async () => {
+    const user = userEvent.setup();
+    renderHead();
+
+    const header = screen.getByRole("columnheader", { name: /^SCHEDULE ON/ });
+    const icon = within(header).getByRole("button", { name: "SCHEDULE ON column help" });
+
+    await user.tab();
+
+    expect(icon).toHaveFocus();
+  });
+
+  it("does not add a help icon to Appt Time (open point, not implemented)", () => {
+    renderHead();
+
+    const header = screen.getByRole("columnheader", { name: "APPT TIME" });
+    expect(within(header).queryByRole("img")).not.toBeInTheDocument();
+    expect(getWoTableHeaderTooltip("appt")).toBeUndefined();
+  });
+});