diff --git a/packages/junior-dashboard/e2e/conversations.spec.ts b/packages/junior-dashboard/e2e/conversations.spec.ts
index c8a0fcf129..032a6aa326 100644
--- a/packages/junior-dashboard/e2e/conversations.spec.ts
+++ b/packages/junior-dashboard/e2e/conversations.spec.ts
@@ -134,7 +134,8 @@ test("opens a conversation in the built dashboard", async ({ page }) => {
     .filter({ hasText: /^\$0\.03$/ });
   await expect(costMetric).toHaveCount(1);
   await costMetric.focus();
-  const costTooltip = page.getByRole("tooltip");
+  // Scope past sidebar linked-work tooltips that can stay open on the selected row.
+  const costTooltip = page.getByRole("tooltip").filter({ hasText: /\$/ });
   await expect(costTooltip).toBeVisible();
   const tooltipId = await costTooltip.getAttribute("id");
   expect(tooltipId).toBeTruthy();
diff --git a/packages/junior-dashboard/src/client/conversations/ConversationMeta.tsx b/packages/junior-dashboard/src/client/conversations/ConversationMeta.tsx
index 8d2b8057e2..04c5bdd516 100644
--- a/packages/junior-dashboard/src/client/conversations/ConversationMeta.tsx
+++ b/packages/junior-dashboard/src/client/conversations/ConversationMeta.tsx
@@ -8,6 +8,7 @@ import {
   LockKeyhole,
   TriangleAlert,
 } from "lucide-react";
+import { useSyncExternalStore } from "react";
 import { Link } from "react-router";
 import type { ConversationDetailReport } from "@sentry/junior/api/schema";
 
@@ -22,9 +23,12 @@ import {
 } from "../format";
 import { Tooltip } from "../components/Tooltip";
 import { MetricList, type MetricListItem } from "../components/Metric";
+import { cn } from "../styles";
 import { CostMetric, DurationMetric, TokenMetric } from "./TelemetryMetrics";
 import type { Conversation } from "../types";
 
+const MOBILE_MEDIA_QUERY = "(max-width: 767px)";
+
 /** Show a pending OAuth authorization call-to-action above the composer. */
 export function PendingAuthorization(props: {
   authorization: {
@@ -96,23 +100,233 @@ export function hasConversationAnnotations(
   );
 }
 
-/** Render annotations selected by plugins for a conversation row. */
+/** Render plugin annotations as a newest-first stack in a conversation row. */
 export function ConversationSidebarAnnotations(props: {
   annotations: ConversationDetailReport["sidebarAnnotations"] | undefined;
 }) {
-  if (!props.annotations?.length) return null;
-  return props.annotations.map((summary) => (
+  const annotations = props.annotations;
+  const isMobile = useIsMobileViewport();
+  if (!annotations?.length) return null;
+
+  const details = annotations.map((annotation) =>
+    sidebarAnnotationDetail(annotation),
+  );
+  // Collapse same-label scopes for the stack so one repo doesn't become two
+  // chips. The tooltip still lists every annotation.
+  const stack = collapseSidebarAnnotationStack(annotations);
+
+  return (
+    <Tooltip
+      align="left"
+      content={
+        <ul className="m-0 list-none space-y-1 p-0">
+          {annotations.map((annotation, index) => (
+            <li
+              className="flex min-w-0 items-center gap-1.5"
+              key={`${annotation.key}:${index}`}
+            >
+              {annotation.icon ? (
+                <SidebarAnnotationIcon icon={annotation.icon} />
+              ) : null}
+              <span className="min-w-0 truncate">{details[index]}</span>
+            </li>
+          ))}
+        </ul>
+      }
+      label="Linked work"
+      triggerClassName="min-w-0"
+    >
+      <span
+        aria-label={`Linked work, newest first: ${details.join(", ")}`}
+        className="inline-flex min-w-0 max-w-full items-center"
+      >
+        {isMobile ? (
+          <SidebarAnnotationIconFacepile
+            annotations={stack}
+            // Discs sit on the sidebar panel / row surface (#09090b).
+            cutoutColor="var(--color-dashboard-surface-panel)"
+          />
+        ) : stack.length <= 2 ? (
+          <span className="inline-flex min-w-0 items-center gap-1">
+            {stack.map((annotation) => (
+              <SidebarAnnotationChip
+                annotation={annotation}
+                key={annotation.key}
+              />
+            ))}
+          </span>
+        ) : (
+          <SidebarAnnotationOverflowStack annotations={stack} />
+        )}
+      </span>
+    </Tooltip>
+  );
+}
+
+/** Compact overlapping status chips used by mobile and overflow clusters. */
+function SidebarAnnotationIconFacepile(props: {
+  annotations: NonNullable<ConversationDetailReport["sidebarAnnotations"]>;
+  /**
+   * CSS color for the avatar-stack cutout ring. Must match the surface under
+   * the facepile so lower chips read as clean silhouettes.
+   */
+  cutoutColor: string;
+  className?: string;
+}) {
+  return (
     <span
-      className="inline-flex min-w-0 max-w-full items-center gap-1 truncate"
-      key={summary.key}
-      title={summary.label}
+      className={cn(
+        // Isolate stacking context so z-index only orders chips inside the pile.
+        // Extra right pad keeps the last chip's cutout ring from clipping.
+        "relative isolate inline-flex h-[18px] items-center pr-0.5",
+        props.className,
+      )}
     >
-      {summary.icon ? <SidebarAnnotationIcon icon={summary.icon} /> : null}
-      <span className="min-w-0 truncate whitespace-nowrap font-sans text-dashboard-text-muted">
-        {summary.label}
+      {props.annotations.map((annotation, index) => (
+        <SidebarAnnotationStatusChip
+          annotation={annotation}
+          cutoutColor={props.cutoutColor}
+          key={annotation.key}
+          // Each chip to the right layers above the chip before it.
+          stacked={index > 0}
+          zIndex={index + 1}
+        />
+      ))}
+    </span>
+  );
+}
+
+/** One continuous stack: labeled chip, icon chips, then the count chip. */
+function SidebarAnnotationOverflowStack(props: {
+  annotations: NonNullable<ConversationDetailReport["sidebarAnnotations"]>;
+}) {
+  const [primary, ...overflow] = props.annotations;
+  if (!primary || overflow.length === 0) return null;
+  return (
+    <span className="isolate inline-flex h-5 min-w-0 items-center pr-0.5">
+      <SidebarAnnotationChip annotation={primary} />
+      {overflow.map((annotation, index) => (
+        <SidebarAnnotationStatusChip
+          annotation={annotation}
+          cutoutColor="var(--color-dashboard-surface-panel)"
+          key={annotation.key}
+          stacked
+          zIndex={index + 1}
+        />
+      ))}
+      <span
+        className="relative -ml-1.5 inline-flex h-5 min-w-7 shrink-0 items-center justify-center rounded-full border border-white/12 bg-dashboard-control px-1.5 font-mono text-2xs leading-none text-dashboard-text-muted"
+        style={{
+          boxShadow: "0 0 0 2px var(--color-dashboard-surface-panel)",
+          zIndex: overflow.length + 1,
+        }}
+      >
+        +{overflow.length}
+      </span>
+    </span>
+  );
+}
+
+function SidebarAnnotationChip(props: {
+  annotation: NonNullable<
+    ConversationDetailReport["sidebarAnnotations"]
+  >[number];
+}) {
+  return (
+    <span className="inline-flex h-5 min-w-0 max-w-28 shrink-0 items-center gap-1 truncate rounded-full border border-white/10 bg-dashboard-control px-1.5 font-sans text-2xs leading-none text-dashboard-text-muted">
+      {props.annotation.icon ? (
+        <SidebarAnnotationIcon
+          decorative
+          icon={props.annotation.icon}
+          size={11}
+        />
+      ) : null}
+      <span className="min-w-0 truncate whitespace-nowrap">
+        {props.annotation.label}
       </span>
     </span>
-  ));
+  );
+}
+
+/** Icon-only chip that matches labeled-chip chrome and stacks like a facepile. */
+function SidebarAnnotationStatusChip(props: {
+  annotation: NonNullable<
+    ConversationDetailReport["sidebarAnnotations"]
+  >[number];
+  cutoutColor: string;
+  stacked?: boolean;
+  zIndex: number;
+}) {
+  const tone = props.annotation.icon
+    ? SIDEBAR_ICON_PRESENTATION[props.annotation.icon]
+    : undefined;
+  return (
+    <span
+      aria-hidden="true"
+      className={cn(
+        // Same border + fill language as labeled chips so the stack reads as
+        // real chips, not floating glyphs. Box-shadow cutout (not border) keeps
+        // layout at 18px while punching a surface-colored ring through the chip
+        // underneath — classic avatar-facepile silhouette.
+        "relative box-border inline-flex size-[18px] shrink-0 items-center justify-center rounded-full border border-white/12 bg-dashboard-control",
+        props.stacked && "-ml-2",
+      )}
+      style={{
+        boxShadow: `0 0 0 2px ${props.cutoutColor}`,
+        zIndex: props.zIndex,
+      }}
+      title={tone?.label}
+    >
+      {props.annotation.icon ? (
+        <SidebarAnnotationIcon
+          decorative
+          icon={props.annotation.icon}
+          size={11}
+        />
+      ) : (
+        <span className="font-sans text-2xs font-semibold leading-none text-dashboard-text-muted">
+          {props.annotation.label.slice(0, 1)}
+        </span>
+      )}
+    </span>
+  );
+}
+
+function useIsMobileViewport(): boolean {
+  return useSyncExternalStore(
+    (onStoreChange) => {
+      if (typeof window === "undefined") return () => {};
+      const media = window.matchMedia(MOBILE_MEDIA_QUERY);
+      media.addEventListener("change", onStoreChange);
+      return () => media.removeEventListener("change", onStoreChange);
+    },
+    () =>
+      typeof window !== "undefined" &&
+      window.matchMedia(MOBILE_MEDIA_QUERY).matches,
+    () => false,
+  );
+}
+
+function collapseSidebarAnnotationStack(
+  annotations: NonNullable<ConversationDetailReport["sidebarAnnotations"]>,
+): NonNullable<ConversationDetailReport["sidebarAnnotations"]> {
+  const seen = new Set<string>();
+  return annotations.filter((annotation) => {
+    if (seen.has(annotation.label)) return false;
+    seen.add(annotation.label);
+    return true;
+  });
+}
+
+function sidebarAnnotationDetail(annotation: {
+  key: string;
+  label: string;
+}): string {
+  // Prefer the plugin key when it carries a fuller resource identity than the
+  // compact label (for example owner/repo#123 vs repo).
+  return annotation.key.includes("/") || annotation.key.includes("#")
+    ? annotation.key
+    : annotation.label;
 }
 
 type SidebarAnnotationIconName = NonNullable<
@@ -146,16 +360,31 @@ const SIDEBAR_ICON_PRESENTATION = {
 function SidebarAnnotationIcon(props: {
   icon: SidebarAnnotationIconName;
   size?: number;
+  /** Hide accessible name when a parent already labels the control. */
+  decorative?: boolean;
 }) {
   const presentation = SIDEBAR_ICON_PRESENTATION[props.icon];
+  const size = props.size ?? 11;
   return (
-    <span className={`shrink-0 ${presentation.className}`} title={presentation.label}>
+    <span
+      aria-hidden={props.decorative ? true : undefined}
+      className={cn(
+        "inline-flex shrink-0 items-center justify-center leading-none",
+        presentation.className,
+      )}
+      // Fixed box stops lucide/svg metrics from shifting chip/disc baselines.
+      style={{ width: size, height: size }}
+      title={props.decorative ? undefined : presentation.label}
+    >
       <presentation.Icon
         aria-hidden="true"
-        size={props.size ?? 11}
+        className="block"
+        size={size}
         strokeWidth={2.25}
       />
-      <span className="sr-only">{presentation.label}</span>
+      {props.decorative ? null : (
+        <span className="sr-only">{presentation.label}</span>
+      )}
     </span>
   );
 }
diff --git a/packages/junior-dashboard/src/client/conversations/ConversationSidebar.tsx b/packages/junior-dashboard/src/client/conversations/ConversationSidebar.tsx
index 26cdf7f3de..1719fd7893 100644
--- a/packages/junior-dashboard/src/client/conversations/ConversationSidebar.tsx
+++ b/packages/junior-dashboard/src/client/conversations/ConversationSidebar.tsx
@@ -190,10 +190,14 @@ function ConversationSidebarRow(props: {
     includeId: false,
   });
   const title = conversationDisplayTitle(props.conversation);
+  const hasAnnotations = Boolean(props.conversation.sidebarAnnotations?.length);
+  // Linked work is denser and more actionable than channel; hide channel when
+  // annotations own the meta row.
+  const showLocation = Boolean(location) && !hasAnnotations;
   const hasMeta =
-    Boolean(location) ||
+    showLocation ||
     props.conversation.visibility === "private" ||
-    Boolean(props.conversation.sidebarAnnotations?.length);
+    hasAnnotations;
   return (
     <div className="group relative min-w-0">
       <Link
@@ -229,12 +233,7 @@ function ConversationSidebarRow(props: {
                 className="size-3 shrink-0"
               />
             ) : null}
-            {location ? <span className="truncate">{location}</span> : null}
-            {location && props.conversation.sidebarAnnotations?.length ? (
-              <span aria-hidden="true" className="shrink-0 opacity-50">
-                ·
-              </span>
-            ) : null}
+            {showLocation ? <span className="truncate">{location}</span> : null}
             <ConversationSidebarAnnotations
               annotations={props.conversation.sidebarAnnotations}
             />
diff --git a/packages/junior-dashboard/src/mock-reporting/fixtures.ts b/packages/junior-dashboard/src/mock-reporting/fixtures.ts
index 40ff7a1063..3fe9bbbc73 100644
--- a/packages/junior-dashboard/src/mock-reporting/fixtures.ts
+++ b/packages/junior-dashboard/src/mock-reporting/fixtures.ts
@@ -133,7 +133,13 @@ function activeConversation(nowMs: number): ConversationDetailReport {
     assignedWork: true,
     unfinishedWork: true,
     isPriority: true,
-    sidebarAnnotations: [{ icon: "git-pull-request", key: "github", label: "payments" }],
+    sidebarAnnotations: [
+      {
+        icon: "git-pull-request",
+        key: "getsentry/payments#42",
+        label: "payments",
+      },
+    ],
     annotations: [
       {
         kind: "resource_link",
@@ -331,7 +337,18 @@ function dashboardQaConversation(nowMs: number): ConversationDetailReport {
     assignedWork: true,
     unfinishedWork: true,
     isPriority: true,
-    sidebarAnnotations: [{ icon: "git-pull-request", key: "github", label: "junior" }],
+    sidebarAnnotations: [
+      {
+        icon: "git-pull-request",
+        key: "getsentry/junior#1081",
+        label: "junior",
+      },
+      {
+        icon: "circle-dot",
+        key: "getsentry/junior#1090",
+        label: "junior",
+      },
+    ],
     annotations: [
       {
         kind: "resource_link",
@@ -763,7 +780,23 @@ function longConversation(nowMs: number): ConversationDetailReport {
     assignedWork: true,
     unfinishedWork: true,
     isPriority: true,
-    sidebarAnnotations: [{ icon: "git-pull-request", key: "github", label: "2 repos" }],
+    sidebarAnnotations: [
+      {
+        icon: "circle-dashed",
+        key: "getsentry/junior#2201",
+        label: "junior",
+      },
+      {
+        icon: "git-pull-request",
+        key: "getsentry/payments#91",
+        label: "payments",
+      },
+      {
+        icon: "git-merge",
+        key: "getsentry/relay#44",
+        label: "relay",
+      },
+    ],
     annotations: [
       {
         kind: "resource_link",
@@ -777,23 +810,23 @@ function longConversation(nowMs: number): ConversationDetailReport {
       },
       {
         kind: "resource_link",
-        key: "getsentry/payments#88",
-        label: "getsentry/payments#88",
+        key: "getsentry/payments#91",
+        label: "getsentry/payments#91",
         plugin: "github",
         status: "open",
-        url: "https://github.com/getsentry/payments/issues/88",
+        url: "https://github.com/getsentry/payments/pull/91",
         createdAt: startedAt,
-        updatedAt: iso(Date.parse(startedAt), 70_000),
+        updatedAt: iso(Date.parse(startedAt), 75_000),
       },
       {
         kind: "resource_link",
-        key: "getsentry/payments#91",
-        label: "getsentry/payments#91",
+        key: "getsentry/relay#44",
+        label: "getsentry/relay#44",
         plugin: "github",
-        status: "open",
-        url: "https://github.com/getsentry/payments/pull/91",
+        status: "merged",
+        url: "https://github.com/getsentry/relay/pull/44",
         createdAt: startedAt,
-        updatedAt: iso(Date.parse(startedAt), 75_000),
+        updatedAt: iso(Date.parse(startedAt), 70_000),
       },
     ],
     cumulativeDurationMs: 552_761,
@@ -839,7 +872,18 @@ function incidentConversation(nowMs: number): ConversationDetailReport {
     // Finished links show the final annotation state in the sidebar.
     assignedWork: true,
     finishedWorkAt: iso(nowMs, -42 * 60_000),
-    sidebarAnnotations: [{ icon: "git-merge", key: "github", label: "payments" }],
+    sidebarAnnotations: [
+      {
+        icon: "git-merge",
+        key: "getsentry/payments#77",
+        label: "payments",
+      },
+      {
+        icon: "circle-x",
+        key: "getsentry/payments#61",
+        label: "payments",
+      },
+    ],
     annotations: [
       {
         kind: "resource_link",
@@ -1736,7 +1780,8 @@ export function readMockPeoplePluginReports(
             id: "pull-requests-created",
             type: "bar_chart",
             title: "Pull requests opened",
-            description: "Junior-owned pull requests opened for this person per day",
+            description:
+              "Junior-owned pull requests opened for this person per day",
             timeRangeDays: [7, 30, 90],
             series: [{ key: "created", label: "Opened" }],
             categories: days,
diff --git a/packages/junior-dashboard/tests/dashboard-mock-routes.test.ts b/packages/junior-dashboard/tests/dashboard-mock-routes.test.ts
index c7449b85d9..0d62b924b9 100644
--- a/packages/junior-dashboard/tests/dashboard-mock-routes.test.ts
+++ b/packages/junior-dashboard/tests/dashboard-mock-routes.test.ts
@@ -262,7 +262,16 @@ describe("dashboard canonical-event mock routes", () => {
     );
     expect(dashboardQa.annotations).toHaveLength(2);
     expect(dashboardQa.sidebarAnnotations).toEqual([
-      { icon: "git-pull-request", key: "github", label: "junior" },
+      {
+        icon: "git-pull-request",
+        key: "getsentry/junior#1081",
+        label: "junior",
+      },
+      {
+        icon: "circle-dot",
+        key: "getsentry/junior#1090",
+        label: "junior",
+      },
     ]);
     expect(dashboardQa.unfinishedWork).toBe(true);
 
diff --git a/packages/junior-dashboard/tests/telemetry-components.test.tsx b/packages/junior-dashboard/tests/telemetry-components.test.tsx
index 6b8990da5b..9cc0790c82 100644
--- a/packages/junior-dashboard/tests/telemetry-components.test.tsx
+++ b/packages/junior-dashboard/tests/telemetry-components.test.tsx
@@ -586,19 +586,94 @@ describe("dashboard canonical-event components", () => {
     expect(html).toContain('title="Open pull request"');
   });
 
-  it("renders plugin-selected sidebar annotations", () => {
-    const html = renderToStaticMarkup(
+  it("labels one or two scopes and clusters the rest on desktop", () => {
+    const single = renderToStaticMarkup(
+      <ConversationSidebarAnnotations
+        annotations={[
+          {
+            icon: "circle-dot",
+            key: "getsentry/junior#2",
+            label: "junior",
+          },
+        ]}
+      />,
+    );
+    expect(single).toContain(">junior<");
+    expect(single).toContain("getsentry/junior#2");
+
+    const dual = renderToStaticMarkup(
+      <ConversationSidebarAnnotations
+        annotations={[
+          {
+            icon: "circle-dot",
+            key: "getsentry/junior#2",
+            label: "junior",
+          },
+          {
+            icon: "git-merge",
+            key: "getsentry/payments#1",
+            label: "payments",
+          },
+        ]}
+      />,
+    );
+    expect(dual).toContain(
+      'aria-label="Linked work, newest first: getsentry/junior#2, getsentry/payments#1"',
+    );
+    expect(dual.indexOf(">junior<")).toBeLessThan(dual.indexOf(">payments<"));
+    expect(dual).not.toContain(">+1<");
+    // Chip icons are decorative; the parent aria-label carries the identity.
+    expect(dual).toContain("lucide-circle-dot");
+    expect(dual).toContain("lucide-git-merge");
+
+    const stacked = renderToStaticMarkup(
+      <ConversationSidebarAnnotations
+        annotations={[
+          {
+            icon: "circle-dashed",
+            key: "getsentry/junior#3",
+            label: "junior",
+          },
+          {
+            icon: "circle-dot",
+            key: "getsentry/payments#2",
+            label: "payments",
+          },
+          {
+            icon: "git-merge",
+            key: "getsentry/relay#1",
+            label: "relay",
+          },
+        ]}
+      />,
+    );
+    expect(stacked).toContain(">junior<");
+    expect(stacked).toContain(">+2<");
+    expect(stacked).not.toContain(">payments<");
+    expect(stacked).not.toContain(">relay<");
+    expect(stacked).toContain("getsentry/payments#2");
+    expect(stacked).toContain("getsentry/relay#1");
+
+    const sameRepo = renderToStaticMarkup(
       <ConversationSidebarAnnotations
         annotations={[
-          { icon: "git-merge", key: "github", label: "2 repos" },
-          { icon: "git-pull-request", key: "open-pr", label: "junior" },
+          {
+            icon: "circle-dot",
+            key: "getsentry/junior#2",
+            label: "junior",
+          },
+          {
+            icon: "git-merge",
+            key: "getsentry/junior#1",
+            label: "junior",
+          },
         ]}
       />,
     );
-    expect(html).toContain("2 repos");
-    expect(html).toContain("Merged");
-    expect(html).toContain("Open pull request");
-    expect(html).toContain("min-w-0 truncate whitespace-nowrap font-sans");
+    expect(sameRepo).toContain(">junior<");
+    expect(sameRepo.match(/>junior</g)).toHaveLength(1);
+    expect(sameRepo).not.toContain(">+1<");
+    expect(sameRepo).toContain("getsentry/junior#1");
   });
 
   it("distinguishes initial detail failures from stale refresh failures", () => {
diff --git a/packages/junior-github/src/annotations.ts b/packages/junior-github/src/annotations.ts
index e610223305..d47e24ef47 100644
--- a/packages/junior-github/src/annotations.ts
+++ b/packages/junior-github/src/annotations.ts
@@ -3,14 +3,6 @@ import type {
   ConversationSidebarAnnotation,
 } from "@sentry/junior-plugin-api";
 
-const STATUS_RANK = {
-  warning: 5,
-  open: 4,
-  draft: 3,
-  merged: 2,
-  closed: 1,
-} as const;
-
 const STATUS_ICON = {
   warning: "triangle-alert",
   open: "circle-dot",
@@ -19,18 +11,7 @@ const STATUS_ICON = {
   closed: "circle-x",
 } as const;
 
-type GitHubAnnotationStatus = keyof typeof STATUS_RANK;
-
-function repositoryScope(
-  annotation: ConversationAnnotation,
-): { key: string; label: string } | undefined {
-  try {
-    const [, owner, repo] = new URL(annotation.url).pathname.split("/");
-    return owner && repo ? { key: `${owner}/${repo}`, label: repo } : undefined;
-  } catch {
-    return undefined;
-  }
-}
+type GitHubAnnotationStatus = keyof typeof STATUS_ICON;
 
 function isPullRequestUrl(url: string): boolean {
   try {
@@ -42,38 +23,44 @@ function isPullRequestUrl(url: string): boolean {
 
 function sidebarIconForStatus(
   status: GitHubAnnotationStatus,
-  links: Array<{ isPullRequest: boolean; status: GitHubAnnotationStatus }>,
+  url: string,
 ): ConversationSidebarAnnotation["icon"] {
-  if (
-    status === "open" &&
-    links.some((link) => link.status === "open" && link.isPullRequest)
-  ) {
-    return "git-pull-request";
-  }
+  if (status === "open" && isPullRequestUrl(url)) return "git-pull-request";
   return STATUS_ICON[status];
 }
 
-/** Select the one GitHub annotation summary shown in a conversation row. */
-export function githubSidebarAnnotation(
+function repositoryName(
+  annotation: ConversationAnnotation,
+): string | undefined {
+  try {
+    const [, , repo] = new URL(annotation.url).pathname.split("/");
+    return repo || undefined;
+  } catch {
+    return undefined;
+  }
+}
+
+/** Return GitHub annotations for a conversation row, newest first. */
+export function githubSidebarAnnotations(
   annotations: ConversationAnnotation[],
-): ConversationSidebarAnnotation | undefined {
-  const links = annotations.flatMap((annotation) => {
-    const repo = repositoryScope(annotation);
-    const status = annotation.status as GitHubAnnotationStatus | undefined;
-    return repo && status
-      ? [{ isPullRequest: isPullRequestUrl(annotation.url), repo, status }]
-      : [];
-  });
-  if (links.length === 0) return undefined;
-  const repos = new Map(links.map((link) => [link.repo.key, link.repo.label]));
-  const status = links.reduce<GitHubAnnotationStatus>(
-    (current, link) =>
-      STATUS_RANK[link.status] > STATUS_RANK[current] ? link.status : current,
-    "closed",
-  );
-  return {
-    icon: sidebarIconForStatus(status, links),
-    key: "github",
-    label: repos.size === 1 ? [...repos.values()][0]! : `${repos.size} repos`,
-  };
+): ConversationSidebarAnnotation[] {
+  return annotations
+    .flatMap((annotation) => {
+      const status = annotation.status as GitHubAnnotationStatus | undefined;
+      const label = repositoryName(annotation);
+      return status && label
+        ? [
+            {
+              annotation: {
+                icon: sidebarIconForStatus(status, annotation.url),
+                key: annotation.key,
+                label,
+              },
+              updatedAt: annotation.updatedAt,
+            },
+          ]
+        : [];
+    })
+    .sort((left, right) => right.updatedAt.localeCompare(left.updatedAt))
+    .map(({ annotation }) => annotation);
 }
diff --git a/packages/junior-github/src/plugin.ts b/packages/junior-github/src/plugin.ts
index 0af6b8071e..e27f78741b 100644
--- a/packages/junior-github/src/plugin.ts
+++ b/packages/junior-github/src/plugin.ts
@@ -40,7 +40,7 @@ import type { GitHubDb } from "./db/database.js";
 import { buildGitHubProfileReport } from "./outcomes/profile-report.js";
 import { buildGitHubOutcomeReport } from "./outcomes/report.js";
 import { classifyGitHubPullRequestCommitComposition } from "./pull-request-outcomes/commit-composition.js";
-import { githubSidebarAnnotation } from "./annotations.js";
+import { githubSidebarAnnotations } from "./annotations.js";
 import {
   listGitHubAssignedWork,
   listGitHubFinishedWork,
@@ -742,10 +742,12 @@ export function githubPlugin(
         return {
           annotationsByConversationId: Object.fromEntries(
             ctx.conversationIds.flatMap((conversationId) => {
-              const annotation = githubSidebarAnnotation(
+              const annotations = githubSidebarAnnotations(
                 ctx.annotationsByConversationId[conversationId] ?? [],
               );
-              return annotation ? [[conversationId, [annotation]]] : [];
+              return annotations.length > 0
+                ? [[conversationId, annotations]]
+                : [];
             }),
           ),
         };
diff --git a/packages/junior-github/tests/annotations.test.ts b/packages/junior-github/tests/annotations.test.ts
index 9734fc0a53..08caef1f63 100644
--- a/packages/junior-github/tests/annotations.test.ts
+++ b/packages/junior-github/tests/annotations.test.ts
@@ -3,13 +3,14 @@ import {
   type ConversationAnnotation,
 } from "@sentry/junior-plugin-api";
 import { describe, expect, it } from "vitest";
-import { githubSidebarAnnotation } from "../src/annotations";
+import { githubSidebarAnnotations } from "../src/annotations";
 
 function annotation(
   repo: string,
   number: number,
   status: NonNullable<ConversationAnnotation["status"]>,
   owner = "getsentry",
+  updatedAt = "2026-01-01T00:00:01.000Z",
   kind: "pull" | "issues" = "pull",
 ): ConversationAnnotation {
   return {
@@ -19,73 +20,89 @@ function annotation(
     label: `${owner}/${repo}#${number}`,
     plugin: "github",
     status,
-    updatedAt: "2026-01-01T00:00:01.000Z",
+    updatedAt,
     url: `https://github.com/${owner}/${repo}/${kind}/${number}`,
   };
 }
 
 describe("GitHub conversation sidebar", () => {
-  it("selects repository scope and final status", () => {
-    expect(
-      githubSidebarAnnotation([
-        annotation("junior", 1, "merged"),
-        annotation("junior", 2, "closed"),
-      ]),
-    ).toEqual({ icon: "git-merge", key: "github", label: "junior" });
-    expect(
-      githubSidebarAnnotation([
-        annotation("junior", 1, "merged"),
-        annotation("payments", 2, "open"),
-      ]),
-    ).toEqual({ icon: "git-pull-request", key: "github", label: "2 repos" });
-    expect(
-      githubSidebarAnnotation([
-        annotation("junior", 1, "closed"),
-        annotation("junior", 2, "closed"),
-      ]),
-    ).toEqual({ icon: "circle-x", key: "github", label: "junior" });
+  it("returns every annotation newest first", () => {
+    const sidebar = githubSidebarAnnotations([
+      annotation(
+        "junior",
+        1,
+        "merged",
+        "getsentry",
+        "2026-01-01T00:00:01.000Z",
+      ),
+      annotation(
+        "payments",
+        2,
+        "open",
+        "getsentry",
+        "2026-01-01T00:00:02.000Z",
+      ),
+      annotation(
+        "junior",
+        3,
+        "closed",
+        "getsentry",
+        "2026-01-01T00:00:03.000Z",
+      ),
+    ]);
+
+    expect(sidebar).toEqual([
+      {
+        icon: "circle-x",
+        key: "getsentry/junior#3",
+        label: "junior",
+      },
+      {
+        icon: "git-pull-request",
+        key: "getsentry/payments#2",
+        label: "payments",
+      },
+      {
+        icon: "git-merge",
+        key: "getsentry/junior#1",
+        label: "junior",
+      },
+    ]);
+    expect(() =>
+      conversationSidebarAnnotationSchema.array().parse(sidebar),
+    ).not.toThrow();
   });
 
   it("uses the pull request icon for open pull requests", () => {
-    expect(githubSidebarAnnotation([annotation("junior", 1, "open")])).toEqual({
-      icon: "git-pull-request",
-      key: "github",
-      label: "junior",
-    });
+    expect(githubSidebarAnnotations([annotation("junior", 1, "open")])).toEqual(
+      [
+        {
+          icon: "git-pull-request",
+          key: "getsentry/junior#1",
+          label: "junior",
+        },
+      ],
+    );
   });
 
   it("keeps the issue icon for open issues", () => {
     expect(
-      githubSidebarAnnotation([annotation("junior", 1, "open", "getsentry", "issues")]),
-    ).toEqual({ icon: "circle-dot", key: "github", label: "junior" });
-  });
-
-  it("prefers the pull request icon when open issues and pull requests mix", () => {
-    expect(
-      githubSidebarAnnotation([
-        annotation("junior", 1, "open", "getsentry", "issues"),
-        annotation("junior", 2, "open"),
-      ]),
-    ).toEqual({ icon: "git-pull-request", key: "github", label: "junior" });
-  });
-
-  it("counts repositories with the same name under different owners", () => {
-    expect(
-      githubSidebarAnnotation([
-        annotation("shared", 1, "merged", "getsentry"),
-        annotation("shared", 2, "open", "example"),
+      githubSidebarAnnotations([
+        annotation(
+          "junior",
+          1,
+          "open",
+          "getsentry",
+          "2026-01-01T00:00:01.000Z",
+          "issues",
+        ),
       ]),
-    ).toEqual({ icon: "git-pull-request", key: "github", label: "2 repos" });
-  });
-
-  it("keeps valid 100-character GitHub repository names", () => {
-    const repo = "r".repeat(100);
-    const sidebar = githubSidebarAnnotation([annotation(repo, 1, "open")]);
-    expect(sidebar).toEqual({
-      icon: "git-pull-request",
-      key: "github",
-      label: repo,
-    });
-    expect(() => conversationSidebarAnnotationSchema.parse(sidebar)).not.toThrow();
+    ).toEqual([
+      {
+        icon: "circle-dot",
+        key: "getsentry/junior#1",
+        label: "junior",
+      },
+    ]);
   });
 });
diff --git a/packages/junior-plugin-api/src/annotations.ts b/packages/junior-plugin-api/src/annotations.ts
index 3595c12220..904427a700 100644
--- a/packages/junior-plugin-api/src/annotations.ts
+++ b/packages/junior-plugin-api/src/annotations.ts
@@ -73,8 +73,6 @@ export interface ConversationSidebarHookContext extends PluginContext {
 }
 
 export interface ConversationSidebarResult {
-  annotationsByConversationId: Record<
-    string,
-    ConversationSidebarAnnotation[]
-  >;
+  /** Sidebar annotations in display order. Put the newest annotation first. */
+  annotationsByConversationId: Record<string, ConversationSidebarAnnotation[]>;
 }