diff --git a/packages/cli/src/lib/api/projects.ts b/packages/cli/src/lib/api/projects.ts
index 65085d5e2..68dd36449 100644
--- a/packages/cli/src/lib/api/projects.ts
+++ b/packages/cli/src/lib/api/projects.ts
@@ -28,10 +28,13 @@ import {
 } from "../db/project-cache.js";
 import { getCachedOrganizations } from "../db/regions.js";
 import { type AuthGuardSuccess, withAuthGuard } from "../errors.js";
+import { logger } from "../logger.js";
 import { getApiBaseUrl } from "../sentry-client.js";
 import { buildProjectUrl } from "../sentry-urls.js";
 import { isAllDigits } from "../utils.js";
 
+const log = logger.withTag("api.projects");
+
 import {
   API_MAX_PER_PAGE,
   apiRequestToRegion,
@@ -77,8 +80,8 @@ export async function listProjects(orgSlug: string): Promise<SentryProject[]> {
     const orgs = getCachedOrganizations();
     const orgName = orgs.find((o) => o.slug === orgSlug)?.name ?? orgSlug;
     cacheProjectsForOrg(orgSlug, orgName, allResults);
-  } catch {
-    // Cache population is best-effort — never fail the command
+  } catch (error) {
+    log.debug(`Failed to cache projects for org '${orgSlug}'`, error);
   }
 
   return allResults;
@@ -178,8 +181,8 @@ function seedProjectCaches(
     cacheProjectsForOrg(orgSlug, orgName, [
       { id: project.id, slug: project.slug, name: project.name },
     ]);
-  } catch {
-    // Best-effort — don't let cache failures break project creation
+  } catch (error) {
+    log.debug(`Failed to seed project cache for '${project.slug}'`, error);
   }
   if (dsn) {
     try {
@@ -193,8 +196,8 @@ function seedProjectCaches(
           projectId: project.id,
         });
       }
-    } catch {
-      // Best-effort — don't let cache failures break project creation
+    } catch (error) {
+      log.debug(`Failed to seed DSN key cache for '${project.slug}'`, error);
     }
   }
 }
@@ -509,7 +512,8 @@ export async function findProjectByDsnKey(
             { params: { query: `dsn:${publicKey}` } }
           );
           return data;
-        } catch {
+        } catch (error) {
+          log.debug(`DSN key lookup failed in region '${region.url}'`, error);
           return [];
         }
       })
@@ -631,7 +635,8 @@ export async function tryGetPrimaryDsn(
     const keys = await getProjectKeys(orgSlug, projectSlug);
     const activeKey = keys.find((k) => k.isActive);
     return activeKey?.dsn.public ?? keys[0]?.dsn.public ?? null;
-  } catch {
+  } catch (error) {
+    log.debug(`Failed to fetch DSN for '${orgSlug}/${projectSlug}'`, error);
     return null;
   }
 }
diff --git a/packages/cli/src/lib/db/dsn-cache.ts b/packages/cli/src/lib/db/dsn-cache.ts
index deb5cbdfc..1c1bc1858 100644
--- a/packages/cli/src/lib/db/dsn-cache.ts
+++ b/packages/cli/src/lib/db/dsn-cache.ts
@@ -147,6 +147,14 @@ export function getCachedDsn(directory: string): CachedDsnEntry | undefined {
     return;
   }
 
+  // Rows written by setCachedDetection() with an empty allDsns array store
+  // dsn="" and project_id="". Treat these as cache misses for the single-DSN
+  // path — callers expect a usable DSN when the result is defined.
+  if (!row.dsn) {
+    recordCacheHit("dsn", false);
+    return;
+  }
+
   recordCacheHit("dsn", true);
   touchCacheEntry("dsn_cache", "directory", directory);
   return rowToCachedDsnEntry(row);
diff --git a/packages/cli/src/lib/region.ts b/packages/cli/src/lib/region.ts
index 4ac5fb536..ea9873f3e 100644
--- a/packages/cli/src/lib/region.ts
+++ b/packages/cli/src/lib/region.ts
@@ -10,9 +10,12 @@ import { getConfiguredSentryUrl } from "./constants.js";
 import { getOrgByNumericId, getOrgRegion, setOrgRegion } from "./db/regions.js";
 import { stripDsnOrgPrefix } from "./dsn/index.js";
 import { withAuthGuard } from "./errors.js";
+import { logger } from "./logger.js";
 import { getSdkConfig } from "./sentry-client.js";
 import { getSentryBaseUrl, isSentrySaasUrl } from "./sentry-urls.js";
 
+const log = logger.withTag("region");
+
 /**
  * Promise cache for org region resolution, keyed by orgSlug.
  *
@@ -181,9 +184,8 @@ export async function resolveEffectiveOrg(orgSlug: string): Promise<string> {
     try {
       await resolveOrgRegion(orgSlug);
       return orgSlug;
-    } catch {
-      // Org not found or auth error — fall through to return the original
-      // slug. The downstream API call will produce a relevant error.
+    } catch (error) {
+      log.debug(`resolveOrgRegion failed for '${orgSlug}', using raw slug`, error);
       return orgSlug;
     }
   }
@@ -193,7 +195,8 @@ export async function resolveEffectiveOrg(orgSlug: string): Promise<string> {
   try {
     const { listOrganizationsUncached } = await import("./api-client.js");
     await listOrganizationsUncached();
-  } catch {
+  } catch (error) {
+    log.debug(`Failed to refresh org list for numeric ID '${orgSlug}'`, error);
     return orgSlug;
   }