Oh man, I've had the most tedious mega backdoor Roth rollover process. Once a quarter, I do a MBD rollover from my Fidelity after tax 401k to my Vanguard Roth IRA. I initiated my Q2 rollover July 2nd, and I finally got the notice today that Vanguard has received my funds. Beware - long.

The trouble started when Vanguard received my initial check mid-July and said they would not accept it b/c the name on the check did not match the name on my account. My Fidelity account for some reason didn't have "Jr" listed, whereas my Vanguard account rightfully did. I should add that I had completed several rollovers in the past b/w these two accounts. Back in January, I did run into the same issue but was able to get Vanguard to call Fidelity while I was on the phone line to confirm I was the same person. I had no issues in April. I guess in the mean time, Vanguard had changed their policy and no longer were allowed to do that, so I needed to get a "Medallion Signature Guarantee" that I was the same person on both accounts.

I go to my brick and mortar bank and get the form they need to prove I am the same person. I fill out the paperwork as well as send account statements from both accounts. After 2 weeks of waiting for corporate to approve my paperwork, they finally tell me that they can't verify I am the same person on both accounts. Not sure why.

Next step is to call up Fidelity to get them to add "Jr" to my account. They do so and re-issue the check at the beginning of August and it takes 2 weeks to arrive. Of course the check does not have "Jr" on it. They re-issue it again and rush send it...I get it a few days later and still no "Jr." Finally, on the third try, I get the check that I need. It's August 27th.

I am a bit lazy and don't drop the check into the mail until Labor Day, Sept 3rd. I await an email from Vanguard saying they've received my check and it never comes. I finally accept that it is lost and call Fidelity once more to re-issue the check (as well as my Q3 rollover) on Sept 24th. The check arrives just over a week later, I drop it in the mail on Oct 4th, and apparently it arrived today! Thank god.

I know it's not really Vanguard's fault, but I'm seriously debating switching my Roth IRA over to Fidelity so this can be done much more seamlessly. Not only did I have to shell out for 3 stamps, I missed out on all of the sweet Q3 gainz. Ugghhh. That's it for now...thanks for listening to me vent.