diff --git a/packages/cli/src/__tests__/pi-transcript.test.ts b/packages/cli/src/__tests__/pi-transcript.test.ts
index e2c15c0779..dcf8ff403c 100644
--- a/packages/cli/src/__tests__/pi-transcript.test.ts
+++ b/packages/cli/src/__tests__/pi-transcript.test.ts
@@ -287,6 +287,165 @@ describe('Maka Pi TUI transcript', () => {
     );
   });
 
+  test('status line drops whole low-value segments on overflow, lowest rank first (#3421)', () => {
+    const richMeta = {
+      ...meta(),
+      modelContextWindow: 500_000,
+      usage: {
+        costUsd: 0.42,
+        cacheHitInput: 60,
+        cacheMissInput: 40,
+        contextRemaining: 480_000,
+      },
+    };
+    // Wide: everything renders.
+    const wide = stripAnsi(renderMakaPiStatusLine(richMeta, 120));
+    assert.match(wide, /ctx 20k\/500k 4%/);
+    assert.match(wide, /\$0\.42/);
+    assert.match(wide, /cache 60%/);
+    assert.match(wide, /deepseek · \/tmp\/project/);
+
+    // Below full width, cache drops before cost, and no segment is cut
+    // mid-token while any lower rank still survives.
+    const fullWidth = visibleWidth(wide);
+    const noCache = stripAnsi(renderMakaPiStatusLine(richMeta, fullWidth - 1));
+    assert.doesNotMatch(noCache, /cache/);
+    assert.match(noCache, /\$0\.42/);
+    const noCost = stripAnsi(
+      renderMakaPiStatusLine(richMeta, fullWidth - 'cache 60% · '.length - 1),
+    );
+    assert.doesNotMatch(noCost, /cache|\$0\.42/);
+    assert.match(noCost, /deepseek · \/tmp\/project/);
+  });
+
+  test('status line shortens cwd to its basename before dropping it (#3421)', () => {
+    const line = stripAnsi(
+      renderMakaPiStatusLine(
+        {
+          ...meta(),
+          cwd: '/very/long/nested/project-directory',
+          modelContextWindow: 500_000,
+          usage: {
+            costUsd: 0,
+            cacheHitInput: 1,
+            cacheMissInput: 1,
+            contextRemaining: 480_000,
+          },
+        },
+        // Room for title, mode, model, ctx and a short tail only.
+        'Maka · Auto · deepseek-v4-flash · ctx 20k/500k 4% · project-directory'.length,
+      ),
+    );
+    assert.doesNotMatch(line, /very\/long/);
+    assert.match(line, /project-directory/);
+  });
+
+  test('status line drops a drive-root cwd instead of rendering an empty basename (#3421)', () => {
+    const line = stripAnsi(
+      renderMakaPiStatusLine(
+        {
+          ...meta(),
+          cwd: 'C:\\',
+          modelContextWindow: 500_000,
+          usage: {
+            costUsd: 0.5,
+            cacheHitInput: 1,
+            cacheMissInput: 1,
+            contextRemaining: 480_000,
+          },
+        },
+        40,
+      ),
+    );
+    // C:\ has no useful basename; the segment drops cleanly rather than
+    // leaving an empty segment dangling after the separator.
+    assert.doesNotMatch(line, /C:\\/);
+    assert.doesNotMatch(line, /·\s*$/);
+  });
+
+  test('status line never drops mode, model, goal, or ctx at narrow widths (#3421)', () => {
+    const line = stripAnsi(
+      renderMakaPiStatusLine(
+        {
+          ...meta(),
+          permissionMode: 'bypass',
+          modelContextWindow: 500_000,
+          usage: {
+            costUsd: 9.99,
+            cacheHitInput: 1,
+            cacheMissInput: 1,
+            contextRemaining: 480_000,
+          },
+          goal: {
+            goalId: 'goal-1',
+            revision: 1,
+            sessionId: 'session-1',
+            condition: 'Ship it',
+            setAt: Date.now() - 60_000,
+            iterations: 1,
+            maxIterations: 50,
+            consecutiveNoProgress: 0,
+            blockCap: 8,
+            tokenBudget: null,
+            tokensSpent: 0,
+            lastReason: null,
+            achievedAt: null,
+            pausedAt: null,
+            status: 'active' as const,
+          },
+        },
+        75,
+      ),
+    );
+    assert.match(line, /Full access/);
+    assert.match(line, /deepseek-v4-flash/);
+    assert.match(line, /goal 1\/50/);
+    assert.match(line, /ctx 20k\/500k 4%/);
+    assert.doesNotMatch(line, /\$9\.99|cache|deepseek ·|tmp\/project/);
+  });
+
+  test('status line compacts every critical segment before the narrow-width fallback (#3421)', () => {
+    const metadata = {
+      ...meta(),
+      permissionMode: 'bypass',
+      model: 'anthropic/claude-opus-4-1-very-long',
+      modelContextWindow: 500_000,
+      usage: {
+        costUsd: 9.99,
+        cacheHitInput: 1,
+        cacheMissInput: 1,
+        contextRemaining: 20_000,
+      },
+      goal: {
+        goalId: 'goal-1',
+        revision: 1,
+        sessionId: 'session-1',
+        condition: 'Ship it',
+        setAt: Date.now() - 60_000,
+        iterations: 1,
+        maxIterations: 50,
+        consecutiveNoProgress: 0,
+        blockCap: 8,
+        tokenBudget: null,
+        tokensSpent: 0,
+        lastReason: null,
+        achievedAt: null,
+        pausedAt: null,
+        status: 'active' as const,
+      },
+    };
+
+    for (const width of [40, 70, 80]) {
+      const line = stripAnsi(renderMakaPiStatusLine(metadata, width));
+      assert.ok(visibleWidth(line) <= width);
+      assert.match(line, /Maka/);
+      assert.match(line, /Full/);
+      assert.match(line, /anthropic/);
+      assert.match(line, /(?:goal |g)1\/50/);
+      assert.match(line, /(?:ctx .*96%|c96%)/);
+    }
+  });
+
   test('keeps assistant text after a tool call visible after the tool block', () => {
     const state = createMakaPiTranscriptState();
     appendUserPrompt(state, 'inspect the package');
diff --git a/packages/cli/src/__tests__/pi-tui-runner.test.ts b/packages/cli/src/__tests__/pi-tui-runner.test.ts
index dfcbed939f..f21a769c36 100644
--- a/packages/cli/src/__tests__/pi-tui-runner.test.ts
+++ b/packages/cli/src/__tests__/pi-tui-runner.test.ts
@@ -3506,7 +3506,9 @@ describe('Maka Pi TUI runner', () => {
   });
 
   test('restores switched session state from stored messages', async () => {
-    const terminal = new FakeTerminal();
+    // 120 cols: the status line fits every segment, so the usage segments this
+    // test asserts (ctx, cache) are not priority-dropped (#3421).
+    const terminal = new FakeTerminal(120);
     const driver = new SlashCommandDriver(
       [fakeSessionSummary('session-2', '/repo')],
       new Map([
diff --git a/packages/cli/src/pi-transcript.ts b/packages/cli/src/pi-transcript.ts
index b514cb5f78..89f8bce0be 100644
--- a/packages/cli/src/pi-transcript.ts
+++ b/packages/cli/src/pi-transcript.ts
@@ -45,6 +45,7 @@ import {
 } from '@maka/core/tool-result-status';
 import { type ShellRunUpdate } from '@maka/core/events';
 import { homedir } from 'node:os';
+import { basename } from 'node:path';
 import type { MakaSessionDriver, MakaSideConversationParentStatus } from './session-driver.js';
 import { BoundedChunkBuffer } from './bounded-chunk-buffer.js';
 import { ansi } from './tui-ansi.js';
@@ -1336,38 +1337,69 @@ export function renderMakaPiStatusLine(metadata: MakaPiTranscriptMetadata, width
     return fitLine(ansi.dim(sideConversationStatusLineText(metadata.sideConversation)), safeWidth);
   }
   const sep = ansi.dim(' · ');
-  const parts: string[] = [
-    ansi.bold(metadata.title),
-    ansi.dim(permissionModeLabel(metadata.permissionMode)),
-    ansi.dim(metadata.model),
+  // #3421: segments carry a dropRank so overflow drops whole low-value
+  // segments instead of cutting the chain mid-token from the right.
+  // Lower ranks drop first; segments without a rank never drop:
+  // title, permission mode and goal are safety-relevant, ctx is the
+  // context budget, model is the session's identity.
+  const parts: MakaPiStatusLineSegment[] = [
+    {
+      text: ansi.bold(metadata.title),
+      compactRank: 1,
+      shortenedText: ansi.bold(fitLine(metadata.title, 7)),
+    },
+    {
+      text: ansi.dim(permissionModeLabel(metadata.permissionMode)),
+      compactRank: 4,
+      shortenedText: ansi.dim(compactPermissionModeLabel(metadata.permissionMode)),
+    },
+    {
+      text: ansi.dim(metadata.model),
+      compactRank: 0,
+      shortenedText: ansi.dim(fitLine(metadata.model, 11)),
+    },
   ];
   if (metadata.sideConversation?.view === 'parent') {
-    parts.push(ansi.dim(sideConversationStatusLineText(metadata.sideConversation)));
+    parts.push({
+      text: ansi.dim(sideConversationStatusLineText(metadata.sideConversation)),
+      dropRank: 4,
+    });
   }
   // #1064: omit thinking:default — it is noise before the user explicitly
   // changes the level. Only a non-default, explicitly set level shows.
   if (metadata.thinkingLevel) {
-    parts.push(ansi.dim(`thinking:${metadata.thinkingLevel}`));
+    parts.push({ text: ansi.dim(`thinking:${metadata.thinkingLevel}`), dropRank: 3 });
   }
   if (metadata.orchestrationMode === 'swarm') {
-    parts.push(ansi.accent('swarm'));
+    parts.push({ text: ansi.accent('swarm'), dropRank: 4 });
   } else if (metadata.orchestrationMode === 'graph') {
-    parts.push(ansi.accent('graph'));
+    parts.push({ text: ansi.accent('graph'), dropRank: 4 });
   }
   // An autonomous goal burns tokens between prompts; it must never be
   // invisible. Terminal goals show nothing (the desktop chip hides them too).
   if (metadata.goal && isLiveGoalStatus(metadata.goal.status)) {
     const text = goalStatusLineText(metadata.goal, Date.now());
+    const compactStatus =
+      metadata.goal.status === 'active' ? '' : metadata.goal.status === 'paused' ? 'p' : 'w';
+    const compactText = `g${compactStatus}${metadata.goal.iterations}/${metadata.goal.maxIterations}`;
     // paused gets warning salience: the loop stopped burning but stays armed
     // and resumable, which the user must not miss. waiting is a normal
     // transient between turns, so it stays dim like the other chrome.
-    parts.push(
-      metadata.goal.status === 'active'
-        ? ansi.accent(text)
-        : metadata.goal.status === 'paused'
-          ? ansi.yellow(text)
-          : ansi.dim(text),
-    );
+    parts.push({
+      text:
+        metadata.goal.status === 'active'
+          ? ansi.accent(text)
+          : metadata.goal.status === 'paused'
+            ? ansi.yellow(text)
+            : ansi.dim(text),
+      compactRank: 3,
+      shortenedText:
+        metadata.goal.status === 'active'
+          ? ansi.accent(fitLine(compactText, 8))
+          : metadata.goal.status === 'paused'
+            ? ansi.yellow(fitLine(compactText, 8))
+            : ansi.dim(fitLine(compactText, 8)),
+    });
   }
   const usage = metadata.usage;
   // ctx segment: only show "used" when contextRemaining is available, since
@@ -1380,32 +1412,118 @@ export function renderMakaPiStatusLine(metadata: MakaPiTranscriptMetadata, width
     const pct = Math.round((used / metadata.modelContextWindow) * 100);
     // #1064: color warning — yellow >80%, red >95%, dim otherwise.
     const ctxColor = pct > 95 ? ansi.red : pct > 80 ? ansi.yellow : ansi.dim;
-    parts.push(
-      ctxColor(
+    parts.push({
+      text: ctxColor(
         `ctx ${formatTokenCount(used)}/${formatTokenCount(metadata.modelContextWindow)} ${pct}%`,
       ),
-    );
+      compactRank: 2,
+      shortenedText: ctxColor(`c${pct}%`),
+    });
   } else if (metadata.modelContextWindow !== undefined) {
     // #3371: the window is known but no usage has arrived yet (fresh session,
     // or the provider doesn't report per-step input tokens). Degrade
     // explicitly, pi-style, instead of hiding the segment silently — the user
     // can then tell "not measured yet" apart from "window unknown".
-    parts.push(ansi.dim(`ctx ?/${formatTokenCount(metadata.modelContextWindow)}`));
+    parts.push({
+      text: ansi.dim(`ctx ?/${formatTokenCount(metadata.modelContextWindow)}`),
+      compactRank: 2,
+      shortenedText: ansi.dim('c?'),
+    });
   }
   if (usage) {
     if (usage.costUsd > 0) {
-      parts.push(ansi.dim(`$${formatCost(usage.costUsd)}`));
+      parts.push({ text: ansi.dim(`$${formatCost(usage.costUsd)}`), dropRank: 1 });
     }
     const totalCache = usage.cacheHitInput + usage.cacheMissInput;
     if (totalCache > 0) {
       const hitRate = Math.round((usage.cacheHitInput / totalCache) * 100);
-      parts.push(ansi.dim(`cache ${hitRate}%`));
+      parts.push({ text: ansi.dim(`cache ${hitRate}%`), dropRank: 0 });
     }
   }
-  parts.push(ansi.dim(metadata.connectionSlug));
+  parts.push({ text: ansi.dim(metadata.connectionSlug), dropRank: 2 });
   // #1064: shorten cwd to ~-relative path instead of the full path.
-  parts.push(ansi.dim(shortenCwd(metadata.cwd)));
-  return fitLine(parts.join(sep), safeWidth);
+  const cwd = shortenCwd(metadata.cwd);
+  // cwd degrades progressively (full → basename → dropped), after every
+  // ranked segment above but before the final truncation fallback. A drive
+  // root (C:\) or filesystem root has no useful basename — empty, or the
+  // path itself — so it drops directly instead of rendering an empty
+  // segment after the separator.
+  const cwdBase = basename(cwd);
+  parts.push({
+    text: ansi.dim(cwd),
+    dropRank: 5,
+    shortenedText: cwdBase === '' || cwdBase === cwd ? undefined : ansi.dim(cwdBase),
+  });
+  return fitStatusLine(parts, sep, safeWidth);
+}
+
+interface MakaPiStatusLineSegment {
+  text: string;
+  /** Overflow drops whole segments lowest-rank-first; undefined never drops. */
+  dropRank?: number;
+  /** Critical segments shorten in this order after every droppable segment is gone. */
+  compactRank?: number;
+  /** Progressive fallback tried before this segment is dropped entirely. */
+  shortenedText?: string;
+}
+
+function fitStatusLine(segments: MakaPiStatusLineSegment[], sep: string, width: number): string {
+  const compactSep = ansi.dim(' ');
+  let activeSep = sep;
+  const lineWidth = (segs: MakaPiStatusLineSegment[]): number =>
+    visibleWidth(segs.map((segment) => segment.text).join(activeSep));
+  let kept = segments;
+  // Drop whole low-value segments, lowest rank first, re-checking after each
+  // rank so the fewest possible segments are sacrificed.
+  while (lineWidth(kept) > width) {
+    const dropRanks = kept.flatMap((segment) =>
+      segment.dropRank !== undefined ? [segment.dropRank] : [],
+    );
+    if (dropRanks.length > 0) {
+      const lowest = Math.min(...dropRanks);
+      // A droppable segment with a shortened form degrades before disappearing.
+      const shorten = kept.find(
+        (segment) => segment.dropRank === lowest && segment.shortenedText !== undefined,
+      );
+      if (shorten) {
+        kept = kept.map((segment) =>
+          segment === shorten
+            ? { ...segment, text: segment.shortenedText ?? segment.text, shortenedText: undefined }
+            : segment,
+        );
+      } else {
+        kept = kept.filter((segment) => segment.dropRank !== lowest);
+      }
+      continue;
+    }
+
+    const compactRanks = kept.flatMap((segment) =>
+      segment.compactRank !== undefined && segment.shortenedText !== undefined
+        ? [segment.compactRank]
+        : [],
+    );
+    if (compactRanks.length === 0) break;
+    const nextRank = Math.min(...compactRanks);
+    const shorten = kept.find(
+      (segment) => segment.compactRank === nextRank && segment.shortenedText !== undefined,
+    );
+    if (!shorten) break;
+    kept = kept.map((segment) =>
+      segment === shorten
+        ? { ...segment, text: segment.shortenedText ?? segment.text, shortenedText: undefined }
+        : segment,
+    );
+    // Once critical values compact, reclaim separator chrome too. At widths
+    // below the compact critical seam, fitLine remains the honest fallback.
+    activeSep = compactSep;
+  }
+  return fitLine(kept.map((segment) => segment.text).join(activeSep), width);
+}
+
+function compactPermissionModeLabel(mode: string): string {
+  if (mode === 'bypass') return 'Full';
+  if (mode === 'explore') return 'Read';
+  return 'Auto';
 }
 
 function sideConversationStatusLineText(