diff --git a/VERCEL_DATABASE_SETUP.md b/VERCEL_DATABASE_SETUP.md
new file mode 100644
index 00000000..50b592c2
--- /dev/null
+++ b/VERCEL_DATABASE_SETUP.md
@@ -0,0 +1,88 @@
+# Vercel Database Connection Setup Guide
+
+## Problem
+Your Vercel deployment is losing database connections because the `DATABASE_URL` is incorrectly configured. The error shows Prisma is trying to connect to port 5432 (direct connection) instead of port 6543 (pooled connection).
+
+## Solution: Configure Supabase Connection Pooling
+
+### Step 1: Get Your Supabase Connection URLs
+
+1. Go to your Supabase Dashboard
+2. Navigate to **Settings** → **Database**
+3. Find the **Connection Pooling** section
+
+### Step 2: Set Environment Variables in Vercel
+
+You need to set **two** environment variables in Vercel:
+
+#### 1. `DATABASE_URL` (for queries - REQUIRED)
+- Use the **Connection Pooling** → **Transaction mode** URL
+- Format: `postgresql://postgres.[project-ref]:[password]@aws-0-[region].pooler.supabase.com:6543/postgres?pgbouncer=true`
+- **Important**: Must use port **6543** (not 5432)
+- **Important**: Must include `?pgbouncer=true` parameter
+
+#### 2. `DIRECT_URL` (for migrations - OPTIONAL but recommended)
+- Use the **Connection String** → **URI** (direct connection)
+- Format: `postgresql://postgres:[password]@aws-0-[region].pooler.supabase.com:5432/postgres`
+- This is used only for migrations (`prisma migrate`)
+
+### Step 3: Verify Your Configuration
+
+After setting the environment variables, check your Vercel deployment logs. You should see:
+
+✅ **Correct configuration:**
+- No errors about port 5432
+- Connection pooler URL with port 6543
+
+❌ **Wrong configuration (what you likely have now):**
+- Error: "DATABASE_URL uses pooler hostname but wrong port (5432)"
+- Connection errors: "Can't reach database server"
+
+### Example Correct URLs
+
+**DATABASE_URL (pooled - for queries):**
+```
+postgresql://postgres.abcdefghijklmnop:[YOUR-PASSWORD]@aws-0-us-east-1.pooler.supabase.com:6543/postgres?pgbouncer=true
+```
+
+**DIRECT_URL (direct - for migrations):**
+```
+postgresql://postgres:[YOUR-PASSWORD]@aws-0-us-east-1.pooler.supabase.com:5432/postgres
+```
+
+## Why This Matters
+
+- **Port 6543**: Supabase's connection pooler (PgBouncer) - optimized for serverless
+- **Port 5432**: Direct PostgreSQL connection - not suitable for Vercel serverless
+- **Connection Pooling**: Prevents connection exhaustion in serverless environments
+- **Retry Logic**: The code now includes automatic retry logic for connection failures
+
+## Additional Improvements Made
+
+1. ✅ **Connection Retry Logic**: Automatic retry with exponential backoff (3 attempts)
+2. ✅ **Connection Health Checks**: Validates connection URL on startup
+3. ✅ **Better Error Logging**: Production logs now show connection errors
+4. ✅ **Connection Reuse**: Prisma client is reused across serverless invocations
+
+## Testing
+
+After updating your Vercel environment variables:
+
+1. Redeploy your application
+2. Check Vercel logs for any connection warnings
+3. Test database queries - they should work reliably now
+4. Monitor for connection errors in production
+
+## Troubleshooting
+
+If you still see connection errors:
+
+1. **Verify DATABASE_URL format**: Must have `:6543` and `?pgbouncer=true`
+2. **Check Supabase Dashboard**: Ensure connection pooling is enabled
+3. **Check Vercel Logs**: Look for the validation messages on startup
+4. **Test Connection**: Try connecting manually with the pooled URL
+
+## Need Help?
+
+Check your Vercel deployment logs for specific error messages. The code now provides detailed warnings about incorrect configuration.
+
diff --git a/src/pages/api/trpc/[trpc].ts b/src/pages/api/trpc/[trpc].ts
index 34df55b8..a89080cd 100644
--- a/src/pages/api/trpc/[trpc].ts
+++ b/src/pages/api/trpc/[trpc].ts
@@ -8,12 +8,20 @@ import { createTRPCContext } from "@/server/api/trpc";
 export default createNextApiHandler({
   router: appRouter,
   createContext: createTRPCContext,
-  onError:
-    env.NODE_ENV === "development"
-      ? ({ path, error }) => {
-          console.error(
-            `❌ tRPC failed on ${path ?? "<no-path>"}: ${error.message}`
-          );
-        }
-      : undefined,
+  onError: ({ path, error, type }) => {
+    // Log connection errors in production for debugging
+    const isConnectionError =
+      error.message.includes("Can't reach database server") ||
+      error.message.includes("connection") ||
+      error.message.includes("timeout") ||
+      error.message.includes("P1001") ||
+      error.message.includes("P1008") ||
+      error.message.includes("P1017");
+
+    if (isConnectionError) {
+      console.error(`Database connection error on ${path ?? "<no-path>"}: ${error.message}`);
+    } else if (env.NODE_ENV === "development") {
+      console.error(`tRPC failed on ${path ?? "<no-path>"}: ${error.message}`);
+    }
+  },
 });
diff --git a/src/server/db.ts b/src/server/db.ts
index b84d9dcb..c17a9783 100644
--- a/src/server/db.ts
+++ b/src/server/db.ts
@@ -1,17 +1,110 @@
-import { PrismaClient } from "@prisma/client";
+import { PrismaClient, Prisma } from "@prisma/client";
 
 import { env } from "@/env";
 
+// Connection retry configuration
+const MAX_RETRIES = 3;
+const INITIAL_RETRY_DELAY_MS = 500;
+
+// Check if error is a connection error that should be retried
+const isConnectionError = (error: unknown): boolean => {
+  if (error instanceof Prisma.PrismaClientKnownRequestError) {
+    // P1001: Can't reach database server
+    // P1008: Operations timed out
+    // P1017: Server has closed the connection
+    return ["P1001", "P1008", "P1017"].includes(error.code);
+  }
+  if (error instanceof Prisma.PrismaClientUnknownRequestError) {
+    const message = error.message.toLowerCase();
+    return (
+      message.includes("can't reach database server") ||
+      message.includes("connection") ||
+      message.includes("timeout") ||
+      message.includes("econnrefused")
+    );
+  }
+  // Check for generic connection errors
+  if (error instanceof Error) {
+    const message = error.message.toLowerCase();
+    return (
+      message.includes("can't reach database server") ||
+      message.includes("connection") ||
+      message.includes("timeout") ||
+      message.includes("econnrefused")
+    );
+  }
+  return false;
+};
+
+// Retry wrapper for database operations with exponential backoff
+const withRetry = async <T>(
+  operation: () => Promise<T>,
+  retries = MAX_RETRIES,
+): Promise<T> => {
+  try {
+    return await operation();
+  } catch (error) {
+    if (retries > 0 && isConnectionError(error)) {
+      // Exponential backoff: 500ms, 1000ms, 2000ms
+      const attempt = MAX_RETRIES - retries + 1;
+      const delay = INITIAL_RETRY_DELAY_MS * Math.pow(2, attempt - 1);
+      
+      if (env.NODE_ENV === "development") {
+        console.warn(`Database connection error, retrying in ${delay}ms (${attempt}/${MAX_RETRIES})`);
+      }
+      
+      await new Promise((resolve) => setTimeout(resolve, delay));
+      
+      // Try to reconnect before retrying
+      try {
+        await prismaClient.$connect();
+      } catch {
+        // Ignore connection errors here, let the retry handle it
+      }
+      
+      return withRetry(operation, retries - 1);
+    }
+    throw error;
+  }
+};
+
 const createPrismaClient = () => {
+  // Validate DATABASE_URL is using pooled connection for Supabase
+  const dbUrl = env.DATABASE_URL;
+  if (dbUrl) {
+    try {
+      // Properly parse URL to validate hostname instead of substring matching
+      const url = new URL(dbUrl);
+      const hostname = url.hostname.toLowerCase();
+      const port = url.port ? parseInt(url.port, 10) : (url.protocol === "postgresql:" ? 5432 : null);
+      const isSupabase = hostname.endsWith(".supabase.com") || hostname === "supabase.com";
+      const isPooler = hostname.includes("pooler");
+      const searchParams = new URLSearchParams(url.search);
+      const hasPgbouncer = searchParams.has("pgbouncer") && searchParams.get("pgbouncer") === "true";
+      
+      if (isSupabase) {
+        if (isPooler && port === 5432) {
+          console.error("DATABASE_URL: pooler hostname requires port 6543, not 5432");
+        } else if (!isPooler && port === 5432) {
+          console.error("DATABASE_URL: use connection pooler (port 6543) for serverless");
+        } else if (isPooler && port === 6543 && !hasPgbouncer) {
+          console.warn("DATABASE_URL: add ?pgbouncer=true for optimal performance");
+        }
+      }
+    } catch (error) {
+      // If URL parsing fails, log warning but don't block initialization
+      // Prisma will handle invalid URLs with its own error messages
+      if (env.NODE_ENV === "development") {
+        console.warn("Could not parse DATABASE_URL for validation:", error);
+      }
+    }
+  }
+
   const client = new PrismaClient({
     log:
       env.NODE_ENV === "development" ? ["query", "error", "warn"] : ["error"],
   });
 
-  // In serverless environments (Vercel), we want to avoid eager connection
-  // Prisma will connect lazily on first query, which is better for cold starts
-  // Don't call $connect() here - let Prisma handle connections on-demand
-
   return client;
 };
 
@@ -19,32 +112,60 @@ const globalForPrisma = globalThis as unknown as {
   prisma: ReturnType<typeof createPrismaClient> | undefined;
 };
 
-// Reuse Prisma client across invocations to optimize connection pooling
-// In Vercel serverless, the same container may handle multiple requests
-// Reusing the client prevents creating new connections for each request
-export const db =
-  globalForPrisma.prisma ?? createPrismaClient();
+// Create or reuse Prisma client
+const prismaClient = globalForPrisma.prisma ?? createPrismaClient();
 
-// Store in globalThis for reuse across all environments
-// This is especially important in serverless where the same container
-// may handle multiple requests, allowing connection reuse
 if (!globalForPrisma.prisma) {
-  globalForPrisma.prisma = db;
+  globalForPrisma.prisma = prismaClient;
 }
 
+// Create a wrapper that adds retry logic to all Prisma operations
+// We'll intercept model access and wrap query methods
+const createRetryProxy = <T extends object>(target: T): T => {
+  return new Proxy(target, {
+    get(obj, prop) {
+      const value = obj[prop as keyof T];
+      
+      // If it's a model (user, wallet, etc.), wrap its methods
+      if (value && typeof value === "object" && !prop.toString().startsWith("$")) {
+        return createRetryProxy(value as object);
+      }
+      
+      // If it's a function (query method), wrap it with retry logic
+      if (typeof value === "function") {
+        return (...args: unknown[]) => {
+          return withRetry(() => {
+            const result = value.apply(obj, args);
+            return result instanceof Promise ? result : Promise.resolve(result);
+          });
+        };
+      }
+      
+      return value;
+    },
+  }) as T;
+};
+
+// Export db with retry logic
+export const db = createRetryProxy(prismaClient);
+
 // Graceful shutdown handling
 if (typeof process !== "undefined") {
-  process.on("beforeExit", async () => {
-    await db.$disconnect();
-  });
+  const disconnect = async () => {
+    try {
+      await prismaClient.$disconnect();
+    } catch (error) {
+      // Ignore errors during shutdown
+    }
+  };
 
+  process.on("beforeExit", disconnect);
   process.on("SIGINT", async () => {
-    await db.$disconnect();
+    await disconnect();
     process.exit(0);
   });
-
   process.on("SIGTERM", async () => {
-    await db.$disconnect();
+    await disconnect();
     process.exit(0);
   });
 }