This year, the IRS has mandated e-filing 1099s if you have 10 or more. The natural way to do this is with the IRS's new IRIS system, which has a built-in web interface to file them. Doing this is very straightforward at times and complete guess-work at others.
The first step is to get authorized to use IRIS. To do this, you apply at the TCC portal. You'll have to sign in with your ID.me account, meaning creating an account if you don't already have one. This can be a bit of a challenge for some situations, but is pretty straightforward and you can call them easily for help. Then you select individual or create an organization, and fill out the form. This is easy enough, but note that most organizations will need two people to sign the application so another person will have to also make an ID.me account and sign. To sign, you'll enter your PIN. I had no idea what my PIN was and got initially concerned, but it's not actually a security feature or anything. All you have to do is go back to the main screen after selecting your organization and click "Modify PIN" in the navigation bar and you can just make a new one without any work.
One more thing to note is to be very sure before submitting the application. If you make a mistake (potentially with the other person who needs to sign), there's no way to correct it on your own after signing. You'll have to call the IRS, wait on hold forever, and get someone to get their manager to manually unsubmit it.
After you apply for a TCC, there's a wait. It me about a week and half to get accepted. You'll get a physical letter in the mail with your TCC(s), which are five-uppercase-letter codes. You should probably save this letter, but practically I haven't found a need for it or even knowledge of my TCC. Instead you'll just log in to the Information Return Portal with your ID.me account, and it will just have your TCC linked to your account already. Then you can start a new 1099 of any type right there. Also, a tip is that if you are doing a few, click "Issuer Management" at the bottom and put your issuer's information in to save it as a preset option. Otherwise, you'll have to enter it every single time. It's then pretty simple to manually enter 1099s.
One thing to note is that if you are issuing multiple 1099s to the same entity, you are apparently required to put an account number on each of those to delineate them. It will give you an error afterwards if you don't.
If you have a list of 1099s to issue, that is where things get complicated. There is an option to "Upload CSV with Form Data" and you can then download templates, but they only consist of a header row and there is little obvious instruction on what to put in any rows or how to format it. It kind of drip-feeds you. In the sidebar there's a few guidelines, and it directs you to see the Template Formatting Guidelines. When you go there you see a table of fields with instructions, but it's comparatively very few of them. At the top is seemingly the same template download drop-down, but this is actually a totally different drop-down. To get instructions, you'll ignore the table on the page and select the form you want to file in this drop-down too and click "Download" to download a PDF of instructions in addition to downloading the template the exact same way on the previous screen. From there, it's pretty easy if you know how to format data. Just a couple of notes:
- Dates have to be zero-padded in the "MM/DD/YYYY" format even though the instructions say both that and that it should be digits only. Ignore the IRS's example of a completely random number that makes no sense even as an Excel date.
- You have to very aggressive about stripping out punctuation and mangling names. You can't have commas or ʻokinas or pound signs in addresses. "O'Riley" isn't a valid name. "José" isn't a valid name. "R.R." or "H.W." aren't valid middle initials.
- If you just have a list of TINs and you need to fill in whether they're businesses or individuals, the formulas
=IF(SEARCH("-",V2)=4,"SSN","EIN")and=IF(U2="SSN","I","B")are very helpful. Breaking up names is more tedious.
If you make a mistake and a return is "Accepted with Errors", you can click on that to download a report. Then you can see the "recordId" for each error, which will be 8 digits. This is only the very end of the actual record ID, so when you go to the correct/replace screen, this part might be cut off in the listing. So you might want to click the receipt ID to view the full list of the submission and make note of the full record IDs there to enable you to find a submission where the end got cut off.
I realize none of this is too hard, but hopefully this guidance makes it just a little bit easier.