diff --git a/apps/bff/src/users/users.service.ts b/apps/bff/src/users/users.service.ts
index 0bdcd698..3bfab8c2 100644
--- a/apps/bff/src/users/users.service.ts
+++ b/apps/bff/src/users/users.service.ts
@@ -26,6 +26,7 @@ export interface EnhancedUser extends Omit<User, "createdAt" | "updatedAt"> {
     buildingName?: string | null;
     roomNumber?: string | null;
   };
+  salesforceHealthy?: boolean;
 }
 
 // Salesforce Account interface based on the data model
@@ -81,7 +82,11 @@ export class UsersService {
   ) {}
 
   // Helper function to convert Prisma user to EnhancedUser type
-  private toEnhancedUser(user: PrismaUser, extras: Partial<EnhancedUser> = {}): EnhancedUser {
+  private toEnhancedUser(
+    user: PrismaUser, 
+    extras: Partial<EnhancedUser> = {}, 
+    salesforceHealthy: boolean = true
+  ): EnhancedUser {
     return {
       id: user.id,
       email: user.email,
@@ -93,6 +98,7 @@ export class UsersService {
       emailVerified: user.emailVerified,
       createdAt: user.createdAt,
       updatedAt: user.updatedAt,
+      salesforceHealthy,
       ...extras,
     };
   }
@@ -194,7 +200,7 @@ export class UsersService {
           error: getErrorMessage(error),
           userId: validId,
         });
-        return this.toEnhancedUser(user);
+        return this.toEnhancedUser(user, {}, false);
       }
     } catch (error) {
       this.logger.error("Failed to find user by ID", {
@@ -209,25 +215,29 @@ export class UsersService {
     if (!user) throw new Error("User not found");
 
     const mapping = await this.mappingsService.findByUserId(userId);
-    if (!mapping?.sfAccountId) return this.toEnhancedUser(user);
+    if (!mapping?.sfAccountId) return this.toEnhancedUser(user, {}, true);
 
+    let salesforceHealthy = true;
     try {
       const account = (await this.salesforceService.getAccount(
         mapping.sfAccountId
       )) as SalesforceAccount | null;
-      if (!account) return this.toEnhancedUser(user);
+      if (!account) return this.toEnhancedUser(user, undefined, salesforceHealthy);
 
       return this.toEnhancedUser(user, {
         company: account.Name?.trim() || user.company || undefined,
         email: user.email, // Keep original email for now
         phone: user.phone || undefined, // Keep original phone for now
         // Address temporarily disabled until field issues resolved
-      });
+      }, salesforceHealthy);
     } catch (error) {
+      salesforceHealthy = false;
       this.logger.error("Failed to fetch Salesforce account data", {
         error: getErrorMessage(error),
+        userId,
+        sfAccountId: mapping.sfAccountId,
       });
-      return this.toEnhancedUser(user);
+      return this.toEnhancedUser(user, undefined, salesforceHealthy);
     }
   }
 
diff --git a/apps/bff/src/vendors/salesforce/services/salesforce-account.service.ts b/apps/bff/src/vendors/salesforce/services/salesforce-account.service.ts
index 2b89f249..b18cf494 100644
--- a/apps/bff/src/vendors/salesforce/services/salesforce-account.service.ts
+++ b/apps/bff/src/vendors/salesforce/services/salesforce-account.service.ts
@@ -93,11 +93,9 @@ export class SalesforceAccountService {
     if (!whAccountValue?.trim()) throw new Error("WH Account value is required");
 
     try {
-      const sobject = this.connection.sobject("Account") as unknown as {
-        update: (data: Record<string, unknown>) => Promise<unknown>;
-      };
+      const sobject = this.connection.sobject("Account");
 
-      await sobject.update({
+      await sobject.update?.({
         Id: accountId.trim(),
         WH_Account__c: whAccountValue.trim(),
       });
@@ -146,17 +144,13 @@ export class SalesforceAccountService {
 
       if (existingAccount.totalSize > 0) {
         const accountId = existingAccount.records[0].Id;
-        const sobject = this.connection.sobject("Account") as unknown as {
-          update: (data: Record<string, unknown>) => Promise<unknown>;
-        };
-        await sobject.update({ Id: accountId, ...sfData });
+        const sobject = this.connection.sobject("Account");
+        await sobject.update?.({ Id: accountId, ...sfData });
         return { id: accountId, created: false };
       } else {
-        const sobject = this.connection.sobject("Account") as unknown as {
-          create: (data: Record<string, unknown>) => Promise<SalesforceCreateResult>;
-        };
+        const sobject = this.connection.sobject("Account");
         const result = await sobject.create(sfData);
-        return { id: result.id, created: true };
+        return { id: result.id || '', created: true };
       }
     } catch (error) {
       this.logger.error("Failed to upsert account", {
@@ -189,10 +183,8 @@ export class SalesforceAccountService {
     const validAccountId = this.validateId(accountId);
 
     try {
-      const sobject = this.connection.sobject("Account") as unknown as {
-        update: (data: Record<string, unknown>) => Promise<unknown>;
-      };
-      await sobject.update({ Id: validAccountId, ...updates });
+      const sobject = this.connection.sobject("Account");
+      await sobject.update?.({ Id: validAccountId, ...updates });
     } catch (error) {
       this.logger.error("Failed to update account", {
         error: getErrorMessage(error),
diff --git a/apps/bff/src/vendors/salesforce/services/salesforce-connection.service.ts b/apps/bff/src/vendors/salesforce/services/salesforce-connection.service.ts
index 15ce7976..a783731b 100644
--- a/apps/bff/src/vendors/salesforce/services/salesforce-connection.service.ts
+++ b/apps/bff/src/vendors/salesforce/services/salesforce-connection.service.ts
@@ -9,7 +9,12 @@ import * as path from "path";
 
 export interface SalesforceSObjectApi {
   create: (data: Record<string, unknown>) => Promise<{ id?: string }>;
-  update?: (data: Record<string, unknown>) => Promise<unknown>;
+  update?: (data: Record<string, unknown> & { Id: string }) => Promise<unknown>;
+}
+
+interface SalesforceRetryableSObjectApi extends SalesforceSObjectApi {
+  create: (data: Record<string, unknown>) => Promise<{ id?: string }>;
+  update?: (data: Record<string, unknown> & { Id: string }) => Promise<unknown>;
 }
 
 @Injectable()
@@ -124,13 +129,101 @@ export class SalesforceConnection {
     }
   }
 
-  // Expose connection methods
+  // Expose connection methods with automatic re-authentication
   async query(soql: string): Promise<unknown> {
-    return await this.connection.query(soql);
+    try {
+      return await this.connection.query(soql);
+    } catch (error: any) {
+      // Check if this is a session expiration error
+      if (this.isSessionExpiredError(error)) {
+        this.logger.warn("Salesforce session expired, attempting to re-authenticate");
+        
+        try {
+          // Re-authenticate
+          await this.connect();
+          
+          // Retry the query once
+          this.logger.debug("Retrying query after re-authentication");
+          return await this.connection.query(soql);
+        } catch (retryError) {
+          this.logger.error("Failed to re-authenticate or retry query", {
+            originalError: getErrorMessage(error),
+            retryError: getErrorMessage(retryError),
+          });
+          throw retryError;
+        }
+      }
+      
+      // Re-throw other errors as-is
+      throw error;
+    }
+  }
+
+  private isSessionExpiredError(error: any): boolean {
+    // Check for various session expiration indicators
+    const errorMessage = getErrorMessage(error).toLowerCase();
+    const errorCode = error?.errorCode || error?.name || '';
+    
+    return (
+      errorCode === 'INVALID_SESSION_ID' ||
+      errorMessage.includes('session expired') ||
+      errorMessage.includes('invalid session') ||
+      errorMessage.includes('invalid_session_id') ||
+      (error?.status === 401 && errorMessage.includes('unauthorized'))
+    );
   }
 
   sobject(type: string): SalesforceSObjectApi {
-    return this.connection.sobject(type) as unknown as SalesforceSObjectApi;
+    const originalSObject = this.connection.sobject(type);
+    
+    // Return a wrapper that handles session expiration for SObject operations
+    return {
+      create: async (data: Record<string, unknown>) => {
+        try {
+          return await originalSObject.create(data);
+        } catch (error: any) {
+          if (this.isSessionExpiredError(error)) {
+            this.logger.warn("Salesforce session expired during SObject create, attempting to re-authenticate");
+            
+            try {
+              await this.connect();
+              const newSObject = this.connection.sobject(type);
+              return await newSObject.create(data);
+            } catch (retryError) {
+              this.logger.error("Failed to re-authenticate or retry SObject create", {
+                originalError: getErrorMessage(error),
+                retryError: getErrorMessage(retryError),
+              });
+              throw retryError;
+            }
+          }
+          throw error;
+        }
+      },
+      
+      update: async (data: Record<string, unknown> & { Id: string }) => {
+        try {
+          return await originalSObject.update(data as any);
+        } catch (error: any) {
+          if (this.isSessionExpiredError(error)) {
+            this.logger.warn("Salesforce session expired during SObject update, attempting to re-authenticate");
+            
+            try {
+              await this.connect();
+              const newSObject = this.connection.sobject(type);
+              return await newSObject.update(data as any);
+            } catch (retryError) {
+              this.logger.error("Failed to re-authenticate or retry SObject update", {
+                originalError: getErrorMessage(error),
+                retryError: getErrorMessage(retryError),
+              });
+              throw retryError;
+            }
+          }
+          throw error;
+        }
+      }
+    };
   }
 
   isConnected(): boolean {