Can one of my contractors invoice me through quickbooks?

 Yes, they can, @ebmossappeal.

If you’ve invited your contractor to provide their W-9 and bank account information to you, they’ll be asked to create a QuickBooks Self-Employed (QBSE) account. There, they can create and send you an invoice through their account. 

If this is not the case, you’ll have to manually record your contractor invoice in your account and pay the bill. Let me show you how.

1. Go to the + New menu.
2. Select Bill.
3. From the Vendor drop-down menu, select your preferred contractor.
4. Enter the needed details.
5. When you're done, select Save and close.

You can also utilize this article for more details about the process: Enter bills and record bill payments in QuickBooks Online.

Let me also add these resources that you can read for other ways in paying your contractor and filing your 1099: 

• Pay a contractor with a paper check
• Pay a contractor with direct deposit
• Create and file 1099s using QuickBooks Online

You can always tag me in your reply if there’s anything else you need help in managing your contractor or with your account. I’ll be around to back you up. Take care and always keep safe. 

@JasroV Thanks for the info. Can you confirm, however, that even though I already enabled payments via my bank and Quickbooks i didn't realize that a) the only way to use direct deposit for an indie contractor is the $4/mo add on fee? and b) if I write a "paper check" that is not SENT from quickbooks for me? It is basically just a record of what I have to send manually in the mail by myself if I don't want to pay for direct deposit feature?

I appreciate you posting back here, @ebmossappeal. Let me chime in and clarify things for you. 

When you set up your company payroll for direct deposit, you can add your employees' information. In this case, you'll be charged an additional fee. To learn more about the monthly fees, I encourage you to check your subscription. 

However, if you wish to pay your contractor with paper checks, ensure to set up their vendor parofile. Once done, you can now create a paper check. For your reference, please check out this article: Pay a contractor with a paper check.

I've also added this resource to guide you to prepare the 1099 form: Create and file 1099s using QuickBooks Online.

Don't hesitate to comment down below if you need clarifications. I'll make sure to get back to your right away. Stay safe and have a good one.

Is it possible to set up something that allows me to send automatically a bill to one contractor?

Hey there, @Jessica 820.

Thank you for joining this thread. Allow me to provide the answer you're looking for. 

To clarify, do you need to send it on a regular occurrence? In QuickBooks Online (QBO), you may create templates for recurring transactions, like bills or expenses. This saves time and ensure that repeating transactions are processed as scheduled. However, there isn't an option to send bills to vendors or contractors. If you need to mail them a document indicating the details on the items you need to purchase, you may set up a recurring purchase order (PO). This allows you to send it to your contractor.

Here's how:

1. Go to the Gear icon and then Recurring transactions.
   
2. Click New.
3. Select Purchase Order and then OK.
4. Enter a template name.
5. From the Type drop-down, select Scheduled to create the PO automatically according to the date you specify.
6. On the Create _ days in advance field, enter the number of days before the date set in the "Interval" section you want the bill to be created in advance. 
7. Specify the interval and start date of the recurring transaction.
8. From the End drop-down, specify if you want it to end that entry after a number of occurrences.
9. Fill in the category or item details.
10. Hit Save template.

On the Recurring Transactions page, you'll find the list of the repeating templates you defined. It displays columns including Type, Interval, and Previous Date. Look toward the end of one of these lines. To modify the template, click Edit. For more details about the process, refer to these resources: 

• Create Recurring Transactions
• Set up a recurring bill

After your contractor accepts it and sends the products, record it as a bill or expense in QuickBooks. You can easily add the PO as a line item. This closes the original entry, connects it to the bill, and records the accounting accurately.

Keep me posted on how it goes and let me know if you need further assistance. It's my pleasure to lend a hand. Take care always!