if you need help don't expect to hear back "in a few hours" via email.

The process worked, but a few small tweaks would make it feel fairer and easier. I imported the 4 contractors (all individual/sole contractors) I needed to create 1099s for - that was a pretty simple process. A couple of them trade under company names separate from their personal names, so I put that company name as the first line of the address, since Xero doesn't offer the option that exists on a W-9 to separate out the person's name and business name. Then I got an "error" in my own company details. Turns out it was missing a phone number. I added that, but then it wasn't clear where to jump back into the process. So I closed the window and started over. Then clicked e-file for the 4 contractors, paid my $5.80, felt good. Then noticed that only 2 of them were scheduled for filing. You had look closely to see this - there was no pop-up window saying "2 of your submissions were rejected". Turns out that despite having an address field that initially allows a separation between first line and second line of the address, their system then smushes the two together - and has a character limit (which is not flagged). So the combination of the company name and the mailing address led to an overrun on the character limit. As a result, I had to edit the company name (cut the "LLC" from the end, etc) and the address (make "Street" into "St") to try to compress them together. OK. But once those two forms were "corrected" (i.e. shortened to fit an unspecified constraint on the form), they didn't automatically get scheduled. I clicked a few help articles, but there was nothing to cover the exact situation I ended up in, where their system rejected correct details without forewarning. In the end I had to pay another $5.80 to submit the two forms. In the grand scheme of things this was not a lot of money and I am happy to have gotten it done. But it did feel a bit sketchy and I am sure that was not the intention. Parts of the process felt like 5 stars and parts felt like 1 star. Will upgrade rating if they fix this! (Meaning: work with the format in Xero which allows separate lines in the address field; flag any character limit constraints on the address field or any other field; flag clearly when a form has been rejected and is not scheduled for filing; take payment after the forms are accepted, especially if you don't do the previous 3 things)

Hi Mike, Thanks for using Track1099 for the past two years. We work very hard to be super responsive over email. The documentation of your questions helps us improve the experience of our product for all of our clients, plus it keeps our prices low. We will always answer you same day. Best, S. Lindsey West