diff --git a/apps/api/src/services/repo-service.ts b/apps/api/src/services/repo-service.ts
index be0968fe..ccc6bbc2 100644
--- a/apps/api/src/services/repo-service.ts
+++ b/apps/api/src/services/repo-service.ts
@@ -3,6 +3,7 @@ import { db } from "../db/client.js";
 import { repos, workspaces } from "../db/schema.js";
 import { encrypt, decrypt, ALG_AES_256_GCM_V1 } from "./secret-service.js";
 import { normalizeRepoUrl, parseRepoUrl } from "@optio/shared";
+import { logger } from "../logger.js";
 
 export interface RepoRecord {
   id: string;
@@ -130,7 +131,8 @@ export async function getRepoByUrl(
     conditions.push(eq(repos.workspaceId, workspaceId));
   } else {
     // When no workspace is specified, try the default workspace first,
-    // then fall back to any repo with a NULL workspace_id
+    // then fall back to any repo with a NULL workspace_id,
+    // then fall back to any workspace (for background jobs like ticket sync)
     const defaultWsId = await getDefaultWorkspaceId();
     if (defaultWsId) {
       const [repo] = await db
@@ -139,7 +141,24 @@ export async function getRepoByUrl(
         .where(and(eq(repos.repoUrl, normalized), eq(repos.workspaceId, defaultWsId)));
       if (repo) return decryptRepoRow(repo);
     }
-    conditions.push(isNull(repos.workspaceId));
+    // Try NULL workspace_id
+    const [nullWsRepo] = await db
+      .select()
+      .from(repos)
+      .where(and(eq(repos.repoUrl, normalized), isNull(repos.workspaceId)));
+    if (nullWsRepo) return decryptRepoRow(nullWsRepo);
+    // Final fallback: any workspace (background jobs like ticket sync have no workspace context)
+    const anyRepos = await db.select().from(repos).where(eq(repos.repoUrl, normalized));
+    if (anyRepos.length > 0) {
+      if (anyRepos.length > 1) {
+        logger.warn(
+          { repoUrl: normalized, count: anyRepos.length },
+          "Multiple repos found with same URL across workspaces - returning first match",
+        );
+      }
+      return decryptRepoRow(anyRepos[0]);
+    }
+    return null;
   }
   const [repo] = await db
     .select()
diff --git a/apps/api/src/services/ticket-sync-service.ts b/apps/api/src/services/ticket-sync-service.ts
index 524b76dd..b6a5bfd1 100644
--- a/apps/api/src/services/ticket-sync-service.ts
+++ b/apps/api/src/services/ticket-sync-service.ts
@@ -22,7 +22,7 @@ export async function syncAllTickets(): Promise<number> {
     .where(eq(ticketProviders.enabled, true));
 
   // Fetch configured repos once before the provider loop (avoids redundant queries)
-  const configuredRepos = await db.select({ repoUrl: repos.repoUrl }).from(repos);
+  const configuredRepos = await db.select().from(repos);
 
   let totalSynced = 0;
 
@@ -37,8 +37,11 @@ export async function syncAllTickets(): Promise<number> {
         );
         const credentials = JSON.parse(secretJson);
         mergedConfig = { ...mergedConfig, ...credentials };
-      } catch {
-        // No secrets stored for this provider — use config as-is
+      } catch (secretErr) {
+        logger.warn(
+          { err: secretErr, source: providerConfig.source, id: providerConfig.id },
+          "[ticket-sync] Failed to retrieve secret for provider — using config as-is",
+        );
       }
 
       // GitHub fallback: if no token was supplied via config or provider secret,
@@ -142,6 +145,12 @@ export async function syncAllTickets(): Promise<number> {
         // Resolve agent type: ticket label > repo default > "claude-code"
         const { getRepoByUrl } = await import("./repo-service.js");
         const repoConfig = await getRepoByUrl(repoUrl);
+        if (!repoConfig) {
+          logger.warn(
+            { repoUrl, ticketId: ticket.externalId },
+            "[ticket-sync] Repository configuration not found. Task will be created without workspace context.",
+          );
+        }
         const labelAgent = ticket.labels.includes("codex")
           ? "codex"
           : ticket.labels.includes("copilot")
@@ -157,6 +166,7 @@ export async function syncAllTickets(): Promise<number> {
           ticketSource: ticket.source,
           ticketExternalId: ticket.externalId,
           metadata: { ticketUrl: ticket.url },
+          workspaceId: repoConfig?.workspaceId,
         });
 
         await taskService.transitionTask(task.id, TaskState.QUEUED, "ticket_sync");
diff --git a/packages/shared/src/error-classifier.ts b/packages/shared/src/error-classifier.ts
index 4a8041e8..9b03bc8a 100644
--- a/packages/shared/src/error-classifier.ts
+++ b/packages/shared/src/error-classifier.ts
@@ -48,14 +48,17 @@ const ERROR_PATTERNS: Array<{
     }),
   },
   {
-    pattern: /Secret not found: (\w+)/i,
-    classify: (match) => ({
-      category: "auth",
-      title: `Missing secret: ${match[1]}`,
-      description: `The required secret "${match[1]}" is not configured. The agent needs this credential to run.`,
-      remedy: `Go to Secrets and add "${match[1]}", or re-run the setup wizard.`,
-      retryable: true,
-    }),
+    pattern: /Secret not found: (\w+)|no (\w+) secret found/i,
+    classify: (match) => {
+      const missingSecret = match[1] || match[2];
+      return {
+        category: "auth",
+        title: `Missing secret: ${missingSecret}`,
+        description: `The required secret "${missingSecret}" is not configured. The agent needs this credential to run.`,
+        remedy: `Go to Secrets and add "${missingSecret}", or re-run the setup wizard.`,
+        retryable: false, // Don't retry missing secrets - requires user action
+      };
+    },
   },
   {
     pattern:
@@ -72,7 +75,7 @@ const ERROR_PATTERNS: Array<{
         "  security find-generic-password -s \"Claude Code-credentials\" -w | python3 -c \"import sys,json; print(json.load(sys.stdin)['claudeAiOauth']['accessToken'])\" | pbcopy\n\n" +
         "Or re-run 'claude setup-token' to go through the setup flow again.\n" +
         "Retry the failed tasks after updating the token.",
-      retryable: true,
+      retryable: false,
     }),
   },
   {
@@ -83,7 +86,7 @@ const ERROR_PATTERNS: Array<{
       description: "No Anthropic API key is configured and Claude Code cannot authenticate.",
       remedy:
         "Go to Secrets and add ANTHROPIC_API_KEY, or switch to Max subscription auth in Settings.",
-      retryable: true,
+      retryable: false,
     }),
   },
   {
@@ -94,7 +97,7 @@ const ERROR_PATTERNS: Array<{
       description:
         "No OpenAI API key is configured and the Codex agent cannot authenticate with the OpenAI API.",
       remedy: "Go to Secrets and add OPENAI_API_KEY with a valid OpenAI API key.",
-      retryable: true,
+      retryable: false,
     }),
   },
   {
@@ -105,7 +108,17 @@ const ERROR_PATTERNS: Array<{
       description: "No OpenClaw API key is configured and the OpenClaw agent cannot authenticate.",
       remedy:
         "Go to Secrets and add OPENCLAW_API_KEY, or provide an ANTHROPIC_API_KEY or OPENAI_API_KEY instead.",
-      retryable: true,
+      retryable: false,
+    }),
+  },
+  {
+    pattern: /GEMINI_API_KEY/i,
+    classify: () => ({
+      category: "auth",
+      title: "Gemini API key missing",
+      description: "No Gemini API key is configured and Gemini cannot authenticate.",
+      remedy: "Go to Secrets and add GEMINI_API_KEY with a valid Gemini API key.",
+      retryable: false,
     }),
   },
   {
@@ -117,7 +130,7 @@ const ERROR_PATTERNS: Array<{
         "No valid Copilot token is configured. The Copilot agent requires a GitHub token with Copilot Requests permission and an active Copilot subscription.",
       remedy:
         "Go to Secrets and add COPILOT_GITHUB_TOKEN with a fine-grained PAT that has the Copilot Requests permission. Classic PATs (ghp_) are not supported.",
-      retryable: true,
+      retryable: false,
     }),
   },
   {