diff --git a/src/commands/issue/explain.ts b/src/commands/issue/explain.ts
index 498ba4ee..c364555a 100644
--- a/src/commands/issue/explain.ts
+++ b/src/commands/issue/explain.ts
@@ -10,15 +10,13 @@ import {
   getAutofixState,
   triggerRootCauseAnalysis,
 } from "../../lib/api-client.js";
-import { ApiError } from "../../lib/errors.js";
 import { writeFooter, writeJson } from "../../lib/formatters/index.js";
-import {
-  formatRootCauseList,
-  handleSeerApiError,
-} from "../../lib/formatters/seer.js";
+import { formatRootCauseList } from "../../lib/formatters/seer.js";
+import { trackSeerOutcome } from "../../lib/telemetry.js";
 import { extractRootCauses } from "../../types/seer.js";
 import {
   buildCommandHint,
+  handleSeerCommandError,
   type IssueIdFlags,
   issueIdFlags,
   issueIdPositional,
@@ -120,12 +118,16 @@ export const explainCommand = buildCommand({
       // 4. Extract root causes from steps
       const causes = extractRootCauses(state);
       if (causes.length === 0) {
+        trackSeerOutcome("explain", "no_solution");
         throw new Error(
           "Analysis completed but no root causes found. " +
             "The issue may not have enough context for root cause analysis."
         );
       }
 
+      // Track successful outcome
+      trackSeerOutcome("explain", "success");
+
       // 5. Output results
       if (flags.json) {
         writeJson(stdout, causes);
@@ -140,11 +142,7 @@ export const explainCommand = buildCommand({
         `To create a plan, run: sentry issue plan ${issueId}`
       );
     } catch (error) {
-      // Handle API errors with friendly messages
-      if (error instanceof ApiError) {
-        throw handleSeerApiError(error.status, error.detail, resolvedOrg);
-      }
-      throw error;
+      throw handleSeerCommandError(error, "explain", resolvedOrg);
     }
   },
 });
diff --git a/src/commands/issue/plan.ts b/src/commands/issue/plan.ts
index 3a30b0a6..a4628f51 100644
--- a/src/commands/issue/plan.ts
+++ b/src/commands/issue/plan.ts
@@ -11,13 +11,11 @@ import {
   getAutofixState,
   triggerSolutionPlanning,
 } from "../../lib/api-client.js";
-import { ApiError, ValidationError } from "../../lib/errors.js";
+import { ValidationError } from "../../lib/errors.js";
 import { muted } from "../../lib/formatters/colors.js";
 import { writeJson } from "../../lib/formatters/index.js";
-import {
-  formatSolution,
-  handleSeerApiError,
-} from "../../lib/formatters/seer.js";
+import { formatSolution } from "../../lib/formatters/seer.js";
+import { trackSeerOutcome } from "../../lib/telemetry.js";
 import {
   type AutofixState,
   extractRootCauses,
@@ -26,6 +24,7 @@ import {
 } from "../../types/seer.js";
 import {
   buildCommandHint,
+  handleSeerCommandError,
   type IssueIdFlags,
   issueIdFlags,
   issueIdPositional,
@@ -219,12 +218,14 @@ export const planCommand = buildCommand({
 
       // Handle errors
       if (finalState.status === "ERROR") {
+        trackSeerOutcome("plan", "failed");
         throw new Error(
           "Plan creation failed. Check the Sentry web UI for details."
         );
       }
 
       if (finalState.status === "CANCELLED") {
+        trackSeerOutcome("plan", "failed");
         throw new Error("Plan creation was cancelled.");
       }
 
@@ -233,6 +234,8 @@ export const planCommand = buildCommand({
 
       // Output results
       if (flags.json) {
+        // Track outcome based on whether solution was found
+        trackSeerOutcome("plan", solution ? "success" : "no_solution");
         writeJson(stdout, {
           run_id: finalState.run_id,
           status: finalState.status,
@@ -243,19 +246,17 @@ export const planCommand = buildCommand({
 
       // Human-readable output
       if (solution) {
+        trackSeerOutcome("plan", "success");
         const lines = formatSolution(solution);
         stdout.write(`${lines.join("\n")}\n`);
       } else {
+        trackSeerOutcome("plan", "no_solution");
         stderr.write(
           "No solution found. Check the Sentry web UI for details.\n"
         );
       }
     } catch (error) {
-      // Handle API errors with friendly messages
-      if (error instanceof ApiError) {
-        throw handleSeerApiError(error.status, error.detail, resolvedOrg);
-      }
-      throw error;
+      throw handleSeerCommandError(error, "plan", resolvedOrg);
     }
   },
 });
diff --git a/src/commands/issue/utils.ts b/src/commands/issue/utils.ts
index fc7e3262..b9204c2b 100644
--- a/src/commands/issue/utils.ts
+++ b/src/commands/issue/utils.ts
@@ -12,8 +12,16 @@ import {
 } from "../../lib/api-client.js";
 import { getProjectByAlias } from "../../lib/db/project-aliases.js";
 import { createDsnFingerprint, detectAllDsns } from "../../lib/dsn/index.js";
-import { ApiError, CliError, ContextError } from "../../lib/errors.js";
-import { getProgressMessage } from "../../lib/formatters/seer.js";
+import {
+  ApiError,
+  CliError,
+  ContextError,
+  SeerError,
+} from "../../lib/errors.js";
+import {
+  getProgressMessage,
+  handleSeerApiError,
+} from "../../lib/formatters/seer.js";
 import {
   expandToFullShortId,
   isShortId,
@@ -22,6 +30,7 @@ import {
 } from "../../lib/issue-id.js";
 import { poll } from "../../lib/polling.js";
 import { resolveOrg, resolveOrgAndProject } from "../../lib/resolve-target.js";
+import { type SeerOutcome, trackSeerOutcome } from "../../lib/telemetry.js";
 import type { SentryIssue, Writer } from "../../types/index.js";
 import { type AutofixState, isTerminalStatus } from "../../types/seer.js";
 
@@ -293,6 +302,46 @@ export async function resolveOrgAndIssueId(
   return { org: result.org, issueId: result.issue.id };
 }
 
+/**
+ * Handle and track errors from Seer commands.
+ *
+ * Converts ApiErrors to Seer-specific errors when applicable and
+ * tracks the appropriate telemetry outcome. For timeout errors,
+ * tracks the timeout outcome.
+ *
+ * @param error - The caught error
+ * @param command - The Seer command for telemetry
+ * @param orgSlug - Organization slug for error context
+ * @returns The error to throw (transformed if needed)
+ */
+export function handleSeerCommandError(
+  error: unknown,
+  command: "explain" | "plan",
+  orgSlug: string | undefined
+): Error {
+  // Handle API errors with friendly messages
+  if (error instanceof ApiError) {
+    const seerError = handleSeerApiError(error.status, error.detail, orgSlug);
+    // Track Seer-specific errors vs generic failures
+    const outcome: SeerOutcome =
+      seerError instanceof SeerError ? seerError.reason : "failed";
+    trackSeerOutcome(command, outcome);
+    return seerError;
+  }
+
+  // Track timeout errors from polling
+  if (error instanceof Error && error.message.includes("timed out")) {
+    trackSeerOutcome(command, "timeout");
+    return error;
+  }
+
+  // Re-throw unknown errors without tracking
+  if (error instanceof Error) {
+    return error;
+  }
+  return new Error(String(error));
+}
+
 type PollAutofixOptions = {
   /** Organization slug */
   orgSlug: string;
diff --git a/src/lib/telemetry.ts b/src/lib/telemetry.ts
index 8b58e420..fb547f2e 100644
--- a/src/lib/telemetry.ts
+++ b/src/lib/telemetry.ts
@@ -289,3 +289,34 @@ export function withSerializeSpan<T>(operation: string, fn: () => T): T {
     fn
   );
 }
+
+/** Possible outcomes for Seer commands */
+export type SeerOutcome =
+  | "success"
+  | "timeout"
+  | "failed"
+  | "no_budget"
+  | "no_solution"
+  | "not_enabled"
+  | "ai_disabled";
+
+/**
+ * Track Seer command outcome metrics.
+ *
+ * Increments a counter metric for Seer command outcomes to understand
+ * success/failure patterns across explain and plan commands.
+ *
+ * @param command - The Seer command (explain or plan)
+ * @param outcome - The outcome type (success, timeout, failed, etc.)
+ */
+export function trackSeerOutcome(
+  command: "explain" | "plan",
+  outcome: SeerOutcome
+): void {
+  Sentry.metrics.count("seer.command.outcome", 1, {
+    attributes: {
+      command,
+      outcome,
+    },
+  });
+}