diff --git a/packages/shared/src/pipeline-health.test.ts b/packages/shared/src/pipeline-health.test.ts
new file mode 100644
index 0000000000..05ad3c310a
--- /dev/null
+++ b/packages/shared/src/pipeline-health.test.ts
@@ -0,0 +1,163 @@
+import { describe, expect, it } from "vitest";
+import {
+  computePipelineHealth,
+  type PipelineHealthFailedAutomationInput,
+  type PipelineHealthInput,
+} from "./pipeline-health.js";
+
+describe("computePipelineHealth", () => {
+  const baseInput: PipelineHealthInput = {
+    pipelineId: "pipeline-1",
+    stages: [],
+    agentsById: {},
+    pipelinesById: {},
+  };
+
+  it("emits one warning per failed automation item and stage", () => {
+    const failure: PipelineHealthFailedAutomationInput = {
+      stageId: "stage-1",
+      stageKey: "build",
+      stageName: "Build",
+      caseId: "case-1",
+      caseTitle: "Case 1",
+      error: "Routine timed out",
+    };
+
+    const report = computePipelineHealth({
+      ...baseInput,
+      failedAutomations: [failure],
+    });
+
+    expect(report.warnings).toHaveLength(1);
+    expect(report.warnings[0]).toMatchObject({
+      code: "automation_failed",
+      stageId: "stage-1",
+      stageKey: "build",
+      stageName: "Build",
+      href: "/pipelines/pipeline-1/items/case-1",
+      hrefLabel: "Open item",
+      message: `Automation failed on "Case 1". Open the item to inspect the log and retry it.`,
+    });
+  });
+
+  it("deduplicates duplicate failed automation rows for the same stage and case", () => {
+    const failure: PipelineHealthFailedAutomationInput = {
+      stageId: "stage-1",
+      stageKey: "build",
+      stageName: "Build",
+      caseId: "case-1",
+      caseTitle: "Case 1",
+      error: "Routine timed out",
+    };
+    const duplicateFailure: PipelineHealthFailedAutomationInput = {
+      stageId: "stage-1",
+      stageKey: "build",
+      stageName: "Build",
+      caseId: "case-1",
+      caseTitle: "Case 1",
+      error: "Routine timed out",
+    };
+
+    const report = computePipelineHealth({
+      ...baseInput,
+      failedAutomations: [failure, duplicateFailure],
+    });
+
+    const automationWarnings = report.warnings.filter((warning) => warning.code === "automation_failed");
+
+    expect(automationWarnings).toHaveLength(1);
+  });
+
+  it("keeps separate warnings for different case IDs in the same stage", () => {
+    const firstFailure: PipelineHealthFailedAutomationInput = {
+      stageId: "stage-1",
+      stageKey: "build",
+      stageName: "Build",
+      caseId: "case-1",
+      caseTitle: "Case 1",
+      error: "Routine timed out",
+    };
+    const secondFailure: PipelineHealthFailedAutomationInput = {
+      stageId: "stage-1",
+      stageKey: "build",
+      stageName: "Build",
+      caseId: "case-2",
+      caseTitle: "Case 2",
+      error: "Routine timed out",
+    };
+
+    const report = computePipelineHealth({
+      ...baseInput,
+      failedAutomations: [firstFailure, secondFailure],
+    });
+
+    const automationWarnings = report.warnings.filter((warning) => warning.code === "automation_failed");
+
+    expect(automationWarnings).toHaveLength(2);
+    expect(automationWarnings.map((warning) => warning.href)).toEqual([
+      "/pipelines/pipeline-1/items/case-1",
+      "/pipelines/pipeline-1/items/case-2",
+    ]);
+  });
+
+  it("keeps separate warnings for the same case ID in different stages", () => {
+    const firstFailure: PipelineHealthFailedAutomationInput = {
+      stageId: "stage-1",
+      stageKey: "build",
+      stageName: "Build",
+      caseId: "case-1",
+      caseTitle: "Case 1",
+      error: "Routine timed out",
+    };
+    const secondFailure: PipelineHealthFailedAutomationInput = {
+      stageId: "stage-2",
+      stageKey: "verify",
+      stageName: "Verify",
+      caseId: "case-1",
+      caseTitle: "Case 1",
+      error: "Routine timed out",
+    };
+
+    const report = computePipelineHealth({
+      ...baseInput,
+      failedAutomations: [firstFailure, secondFailure],
+    });
+
+    const automationWarnings = report.warnings.filter((warning) => warning.code === "automation_failed");
+
+    expect(automationWarnings).toHaveLength(2);
+    expect(automationWarnings.map((warning) => warning.stageId)).toEqual(["stage-1", "stage-2"]);
+  });
+
+  it("keeps separate warnings when stage and case IDs would collide with colon-delimited keys", () => {
+    const firstFailure: PipelineHealthFailedAutomationInput = {
+      stageId: "stage:one",
+      stageKey: "build",
+      stageName: "Build",
+      caseId: "case",
+      caseTitle: "Case 1",
+      error: "Routine timed out",
+    };
+    const secondFailure: PipelineHealthFailedAutomationInput = {
+      stageId: "stage",
+      stageKey: "verify",
+      stageName: "Verify",
+      caseId: "one:case",
+      caseTitle: "Case 2",
+      error: "Routine timed out",
+    };
+
+    const report = computePipelineHealth({
+      ...baseInput,
+      failedAutomations: [firstFailure, secondFailure],
+    });
+
+    const automationWarnings = report.warnings.filter((warning) => warning.code === "automation_failed");
+
+    expect(automationWarnings).toHaveLength(2);
+    expect(automationWarnings.map((warning) => warning.href)).toEqual([
+      "/pipelines/pipeline-1/items/case",
+      "/pipelines/pipeline-1/items/one:case",
+    ]);
+  });
+});
diff --git a/packages/shared/src/pipeline-health.ts b/packages/shared/src/pipeline-health.ts
index c2b8a94753..f8b46d2da8 100644
--- a/packages/shared/src/pipeline-health.ts
+++ b/packages/shared/src/pipeline-health.ts
@@ -339,7 +339,15 @@ export function computePipelineHealth(input: PipelineHealthInput): PipelineHealt
     // the pipeline; a blank default in settings is a normal configuration.
   }
 
+  const seenFailedAutomationCaseIdsByStage = new Map<string, Set<string>>();
   for (const failure of input.failedAutomations ?? []) {
+    let seenCaseIds = seenFailedAutomationCaseIdsByStage.get(failure.stageId);
+    if (!seenCaseIds) {
+      seenCaseIds = new Set<string>();
+      seenFailedAutomationCaseIdsByStage.set(failure.stageId, seenCaseIds);
+    }
+    if (seenCaseIds.has(failure.caseId)) continue;
+    seenCaseIds.add(failure.caseId);
     warnings.push({
       code: "automation_failed",
       stageId: failure.stageId,