1. Refer RRS 21.3, yes, she shall. 
2. Retire, yes if the boat taking penalty turns caused injury or serious damage or, despite taking a 
penalty, gained a significant advantage in the race or series by 
her breach her penalty shall be to retire.

She has to make a new, valid, uninterrupted penalty turn for the first infringement because the first attempt failed.
Plus she must make additional penalty turns for the subsequent infringements.

If she failed in the time to sail clear and do her first turn, is she then out of time and her only option is to retire? 

I would think that technically, you get one chance and unless you follow 44.2 exactly then the optional penalty option is lost. “After getting well clear of other boats as soon after the incident as possible, a boat takes a One-Turn or Two-Turns Penalty by …”.  If you collided with other boats while you are doing your turn then almost always you would not have sailed well clear of other boats as soon after the incident as possible so you should retire if you know you broke a rule from the first instance.  A second attempt at the procedure would not be “as soon as possible” by definition.
I suppose in an unusual situation you could sail well clear and then some other boats would sail off their proper course and collide with you.  In that case, they would likely be breaking 23.2 and you could claim exoneration under 43.2a if you can satisfy the “compelled” part.

That being said, below Olympic level, if you did an extra circle (must be radio sailing :-)) I can’t imagine anyone going through with a protest.

Philip Hubbell

Email: pdhubbell@gmail.com

Said Created: Yesterday 02:32

In what way do you say she 'failed?

Here's the relevant part of rule 44.2

There's nothing in there about 'without breaking any other rule'.

 

 A boat taking a penalty shall keep clear of one that is not.

Phil,

I understand rule 21.2, and breach of that rule is the basis of the OP scenario.

I can only repeat my question:

Why do you say that a breach of rule 21.2 causes the taking of a penalty turn in accordance with rule 44.2 to 'fail'?

Because you probably failed to sail well clear first, so you did not comply with the rule on taking the penalty properly. 

Here’s a recent Q&A on interrupted turns … note in this example, no boat broke a rule

https://members.sailing.org/tools/documents/QA2021.006-%5B27261%5D.pdf

In the original scenario there is no claim that she got well clear. (Conversely, the Q&A boat did, but something external happened.)
If she did not, she still must "continue" her efforts to get well clear, then make her first good penalty turns, plus the two new penalties under 21.2.
21.2 is in Part 2, so it is eligible for a turns penalty, not requiring retirement.