diff --git a/web/src/styles/app.css b/web/src/styles/app.css
index 5c8bdbb..d5a9c32 100644
--- a/web/src/styles/app.css
+++ b/web/src/styles/app.css
@@ -607,6 +607,8 @@ img { max-width: 100%; }
 .rule-card.disabled { opacity: .6; }
 .rule-row { display: grid; grid-template-columns: 1fr 1fr 1fr auto; gap: 8px; align-items: center; margin-bottom: 8px; }
 .rule-row.actions { grid-template-columns: 1fr 2fr auto; }
+/* A header typed by hand needs a box of its own, alongside the comparator. */
+.rule-row.named-header { grid-template-columns: 1fr 1fr 1fr 1fr auto; }
 .code { font-family: var(--font-mono); font-size: 12.5px; line-height: 1.5; white-space: pre; overflow: auto; background: var(--bg-sunken); border: 1px solid var(--border); border-radius: var(--radius-sm); padding: 12px; min-height: 240px; width: 100%; resize: vertical; tab-size: 2; }
 .shortcut-grid { display: grid; grid-template-columns: repeat(auto-fill, minmax(300px, 1fr)); gap: 16px 32px; }
 .shortcut-grid h3 { margin: 0 0 6px; font-size: .9em; text-transform: uppercase; letter-spacing: .05em; color: var(--fg-faint); }
diff --git a/web/src/views/settings/RuleDialog.tsx b/web/src/views/settings/RuleDialog.tsx
index 93c3341..d23d682 100644
--- a/web/src/views/settings/RuleDialog.tsx
+++ b/web/src/views/settings/RuleDialog.tsx
@@ -43,41 +43,47 @@ export function RuleDialog({ rule, onClose, onSave, applyMailbox, title, saveLab
           <option value="anyof">any of the following match</option>
         </select>
       </div>
-      {r.tests.map((t, i) => (
-        <div key={i} className="rule-row">
-          <select className="select" value={t.type === "true" ? "true" : t.type === "size" ? "size" : t.type === "body" ? "body" : t.type === "address" ? "address" : HEADER_CHOICES.some((h) => h.value === t.header) ? t.header : "__custom__"} onChange={(e) => {
-            const v = e.target.value;
-            if (v === "size") setTest(i, { type: "size", op: "over", value: 1024 * 1024 });
-            else if (v === "body") setTest(i, { type: "body", op: "contains", value: "" });
-            else if (v === "true") setTest(i, { type: "true" });
-            else if (v === "address") setTest(i, { type: "address", header: "from", part: "domain", op: "is", value: "" });
-            else setTest(i, { type: "header", header: v === "__custom__" ? "" : v, op: "contains", value: "" });
-          }}>
-            {HEADER_CHOICES.map((h) => <option key={h.value} value={h.value}>{h.label}</option>)}
-            <option value="address">Sender domain</option>
-            <option value="size">Message size</option>
-            <option value="body">Body text</option>
-            <option value="true">Always (all messages)</option>
-          </select>
-          {t.type === "header" && !HEADER_CHOICES.some((h) => h.value === t.header && h.value !== "__custom__") ? (
-            <input className="input" placeholder="Header name" value={t.header} onChange={(e) => setTest(i, { ...t, header: e.target.value })} />
-          ) : t.type === "size" ? (
-            <select className="select" value={t.op} onChange={(e) => setTest(i, { ...t, op: e.target.value as "over" | "under" })}><option value="over">is larger than</option><option value="under">is smaller than</option></select>
-          ) : t.type === "body" ? (
-            <select className="select" value={t.op} onChange={(e) => setTest(i, { ...t, op: e.target.value as "contains" | "notcontains" })}><option value="contains">contains</option><option value="notcontains">does not contain</option></select>
-          ) : t.type === "true" ? <span /> : (
-            <select className="select" value={t.op} onChange={(e) => setTest(i, { ...t, op: e.target.value as SieveTest extends { op: infer O } ? O : never })}>
-              {HEADER_OPS.map((o) => <option key={o.value} value={o.value}>{o.label}</option>)}
+      {r.tests.map((t, i) => {
+        // A header the dropdown doesn't list needs a box to type its name in,
+        // which takes a column of its own — the comparator keeps its.
+        const customHeader = t.type === "header" && !HEADER_CHOICES.some((h) => h.value === t.header && h.value !== "__custom__");
+        return (
+          <div key={i} className={`rule-row${customHeader ? " named-header" : ""}`}>
+            <select className="select" value={t.type === "true" ? "true" : t.type === "size" ? "size" : t.type === "body" ? "body" : t.type === "address" ? "address" : HEADER_CHOICES.some((h) => h.value === t.header) ? t.header : "__custom__"} onChange={(e) => {
+              const v = e.target.value;
+              if (v === "size") setTest(i, { type: "size", op: "over", value: 1024 * 1024 });
+              else if (v === "body") setTest(i, { type: "body", op: "contains", value: "" });
+              else if (v === "true") setTest(i, { type: "true" });
+              else if (v === "address") setTest(i, { type: "address", header: "from", part: "domain", op: "is", value: "" });
+              else setTest(i, { type: "header", header: v === "__custom__" ? "" : v, op: "contains", value: "" });
+            }}>
+              {HEADER_CHOICES.map((h) => <option key={h.value} value={h.value}>{h.label}</option>)}
+              <option value="address">Sender domain</option>
+              <option value="size">Message size</option>
+              <option value="body">Body text</option>
+              <option value="true">Always (all messages)</option>
             </select>
-          )}
-          {t.type === "size" ? (
-            <div className="row"><input className="input" type="number" min={1} value={Math.round(t.value / 1024)} onChange={(e) => setTest(i, { ...t, value: Number(e.target.value) * 1024 })} /><span className="muted">KB</span></div>
-          ) : t.type === "true" ? <span /> : t.type === "header" && (t.op === "exists" || t.op === "notexists") ? <span /> : (
-            <input className="input" placeholder={t.type === "address" ? "example.com" : "value"} value={(t as { value: string }).value} onChange={(e) => setTest(i, { ...t, value: e.target.value } as SieveTest)} />
-          )}
-          <button className="icon-btn sm danger" aria-label="Remove condition" onClick={() => setR({ ...r, tests: r.tests.filter((_, j) => j !== i) })} disabled={r.tests.length <= 1}><Trash2 size={16} /></button>
-        </div>
-      ))}
+            {customHeader && t.type === "header" && (
+              <input className="input" placeholder="Header name" aria-label="Header name" value={t.header} onChange={(e) => setTest(i, { ...t, header: e.target.value })} />
+            )}
+            {t.type === "size" ? (
+              <select className="select" value={t.op} onChange={(e) => setTest(i, { ...t, op: e.target.value as "over" | "under" })}><option value="over">is larger than</option><option value="under">is smaller than</option></select>
+            ) : t.type === "body" ? (
+              <select className="select" value={t.op} onChange={(e) => setTest(i, { ...t, op: e.target.value as "contains" | "notcontains" })}><option value="contains">contains</option><option value="notcontains">does not contain</option></select>
+            ) : t.type === "true" ? <span /> : (
+              <select className="select" value={t.op} onChange={(e) => setTest(i, { ...t, op: e.target.value as SieveTest extends { op: infer O } ? O : never })}>
+                {HEADER_OPS.map((o) => <option key={o.value} value={o.value}>{o.label}</option>)}
+              </select>
+            )}
+            {t.type === "size" ? (
+              <div className="row"><input className="input" type="number" min={1} value={Math.round(t.value / 1024)} onChange={(e) => setTest(i, { ...t, value: Number(e.target.value) * 1024 })} /><span className="muted">KB</span></div>
+            ) : t.type === "true" ? <span /> : t.type === "header" && (t.op === "exists" || t.op === "notexists") ? <span /> : (
+              <input className="input" placeholder={t.type === "address" ? "example.com" : "value"} value={(t as { value: string }).value} onChange={(e) => setTest(i, { ...t, value: e.target.value } as SieveTest)} />
+            )}
+            <button className="icon-btn sm danger" aria-label="Remove condition" onClick={() => setR({ ...r, tests: r.tests.filter((_, j) => j !== i) })} disabled={r.tests.length <= 1}><Trash2 size={16} /></button>
+          </div>
+        );
+      })}
       <button className="btn btn-ghost btn-sm" onClick={() => setR({ ...r, tests: [...r.tests, { type: "header", header: "subject", op: "contains", value: "" }] })}><Plus size={14} /> Add condition</button>
 
       <div className="row" style={{ margin: "16px 0 8px" }}><span className="label">Then</span></div>
diff --git a/web/src/views/settings/__tests__/rule-dialog-header.test.tsx b/web/src/views/settings/__tests__/rule-dialog-header.test.tsx
new file mode 100644
index 0000000..8022f4b
--- /dev/null
+++ b/web/src/views/settings/__tests__/rule-dialog-header.test.tsx
@@ -0,0 +1,67 @@
+import { act } from "react";
+import { createRoot, type Root } from "react-dom/client";
+import { afterEach, beforeEach, describe, expect, it } from "vitest";
+import { RuleDialog } from "../RuleDialog";
+import { newRule } from "@/lib/sieve";
+
+(globalThis as { IS_REACT_ACT_ENVIRONMENT?: boolean }).IS_REACT_ACT_ENVIRONMENT = true;
+
+/**
+ * Choosing "Other header…" used to put the header-name box in the column the
+ * comparator lived in, so the comparator vanished: whatever it happened to be
+ * (contains) was what you were stuck with. Both belong in the row.
+ */
+describe("RuleDialog custom headers", () => {
+  let host: HTMLDivElement;
+  let root: Root;
+
+  /** The condition row's own selects: [field, comparator]. */
+  const selects = () => Array.from(document.querySelectorAll<HTMLSelectElement>(".rule-row:not(.actions) select"));
+  const find = (sel: string) => document.querySelector(sel);
+  const pick = (el: HTMLSelectElement, value: string) => act(() => {
+    el.value = value;
+    el.dispatchEvent(new Event("change", { bubbles: true }));
+  });
+
+  beforeEach(() => {
+    host = document.createElement("div");
+    document.body.appendChild(host);
+    root = createRoot(host);
+  });
+  afterEach(() => {
+    act(() => root.unmount());
+    host.remove();
+  });
+
+  const render = () => act(() => {
+    root.render(<RuleDialog rule={newRule({ id: "r1" })} onClose={() => undefined} onSave={() => undefined} />);
+  });
+
+  it("keeps the comparator when a header is typed by hand", () => {
+    render();
+    // [field, comparator] — the rule starts on "from contains".
+    expect(selects()).toHaveLength(2);
+    pick(selects()[0]!, "__custom__");
+
+    const header = find('input[aria-label="Header name"]') as HTMLInputElement | null;
+    expect(header).not.toBeNull();
+    expect(header!.value).toBe("");
+    const ops = selects()[1]!;
+    expect(ops.value).toBe("contains");
+    expect(Array.from(ops.options).map((o) => o.value)).toContain("matches");
+
+    pick(ops, "matches");
+    expect(selects()[1]!.value).toBe("matches");
+    // The header box is still there, and still has a column of its own.
+    expect(find('input[aria-label="Header name"]')).not.toBeNull();
+    expect(find(".rule-row.named-header")).not.toBeNull();
+  });
+
+  it("leaves a listed header alone", () => {
+    render();
+    expect(find('input[aria-label="Header name"]')).toBeNull();
+    expect(find(".rule-row.named-header")).toBeNull();
+    pick(selects()[1]!, "is");
+    expect(selects()[1]!.value).toBe("is");
+  });
+});