Quicken was fairly easy to call and get help from, even though it took me some time to reach someone who could help me. However, it's common for it to be harder to reach someone in technical support versus attempting to reach someone in sales. Given that it's software, technical support probably ends up fielding many of the phone calls, which is also probably why I had to wait for a bit to talk to someone.
Of course, the time of day I called may not have helped. I will note that they don't have phone customer service in the evening hours. I tried calling around 9 p.m. EST the first time and discovered that they seem to keep business hours for their phone support line. As such, I didn't call again until around noon on a Friday, which admittedly was lunchtime and might explain why I had to wait longer to talk to someone.
There are dozens of reasons why someone might find themselves on hold with Quicken. Some people, like me, may need help getting a part of the software to work. While it was loading on my Mac just fine, I was having issues with one of the spreadsheets and wanted someone to talk me through it. I do better talking to a person who can guide me through a process than attempting to do the same on my own after reading an answer in a forum. Others might have questions about the software and whether it has the capabilities to support their needs.
Either way, the customer service wasn't bad, I just had to wait a few minutes. The directory was easy enough to get through. When I first called, an automated voice said, "Thank you for calling Quicken. For sales, orders, or subscriptions, press 1. For installation, conversion, passwords, or log-in, press 2. For technical support, press 3."
I pressed 3 since I had a technical problem and the automated voice gave me another set of options. It stated, "For problems getting your bank account transactions or connecting to your financial institution, press 1. For questions about paying your bills with Quicken, press 2. For all other technical support questions, press 3."
My question didn't fall into those categories so I pressed 3 and the automated agent asked if I was calling from a Windows computer or a Mac. I pressed 2 to signify I was calling from a Mac and it placed me on hold. The hold music was gentle and non-obtrusive, but it was well over ten minutes before anyone actually took my phone call. Once I got through, the representative was polite and helped me get the software to work.