Adding reefing lines for an additional 3rd mainsail reef

Not exactly correct
Reef pennants cannot be used with sail bags attached to lazy jacks. Reef pennants do not tension the clew & gooseneck, only stow the loose foot in to the boom. You need an outhaul to the clew & a firm fixing such as horns etc for the luff. Simply tying light pennants round the sail does not meet those requirements
And could damage the sail.
 
On non-racing long cruisy occasions I attach a line through the 2nd and 3rd leech cringles as a loop. On the very odd occasion I have needed a 3rd reef after I have put in the 2nd, I attach the 1st reef line to the loop, pull it through, tie it and then off to the mast to put in the reef. Actually I have only done it once - the act of threading the line seems to be enough to placate Aeolus.
 
On non-racing long cruisy occasions I attach a line through the 2nd and 3rd leech cringles as a loop. On the very odd occasion I have needed a 3rd reef after I have put in the 2nd, I attach the 1st reef line to the loop, pull it through, tie it and then off to the mast to put in the reef. Actually I have only done it once - the act of threading the line seems to be enough to placate Aeolus.
Now you mention it, I recall seeing sails with a thin loop 'messenger' between 2nd and third reefs.
 
I normally take in the first reef when I get about 24kn apparent when sailing to windward, a bit less in open water. This means that the second reef comes in at around 28-30kn. The boat, with 110% jib sails very well in 20kn when many boats will be reefed. My cruising grounds have included the Channel and southern North Sea, including a number of 24hr+ trips, but I can’t conceive of a situation where I would need even less sail, given modern forecasts. Those willing to set off into the Channel with a F7 or more in the forecast may well have different needs, and of course those going further afield. I don’t think that I have needed the second reef for a downwind or free sail in open water, though there was one occasion when we did a 2hr passage in the Scheldt in a steady F8 when I probably had two reefs.
Thanks for the feedback. I take onboard your comments but in the areas I sail (Westen Isles to Shetland, west coast of Ireland)… I take the forecasts with a dose of salts… particularly when your going around headlands, katabatic winds inshore and acceleration zones between islands. As an example, this summer we sailed from Harris across the Minch to Skye in a strong wind warning; we were well prepared - deep reefed to my second reef and the the large Genoa changed to a working jib. The forecast weather did not materialise and we felt under powered; it was only when we turned into the Sound of Rassay that the wind shifted 90 and accelerated to 40+ knots that it started to turn sour; we dropped the mainsail completely and furled to a scrap of working jib to beat down to the Isle of Rona. That was one day when I would have really appreciated the 3rd eeef to help me beat more efficiently into the wind.
 
Copy of my article in PBO
When I am sailing I have a short strop permanently fitted to the spinnaker ring on the mast. When visiting crew ask what it is for I tell them that it is for an emergency hand hold when at the mast in case a large wave causes the boat to roll unexpectedly & catches them out Picture A

That is until we are out of sight of land. Then I tell them the real reason I have it!!

As most of my sailing is on my own I try to go on deck as little as possible: hence I have single line reefing. Now I do not wish to get into the debate about this system – it works for me!!. The problem is that whilst it is great for the first & second reefs it needs lines permanently rigged up the leech & the luff of the sail. These have to be gathered in every time the sail is dropped. I can deal with the first two sets of reef lines OK, but they would be so long for the third reef that they would be a serious hassle. Furthermore, I only have to go down to third reef, at the most, once a year, but I hoist & drop the sail dozens of times.

Single line reefing is good but I wanted a bullet proof method of applying the third reef, plus a backup if a reef line were to break. Some single line systems have an array of blocks inside the boom & if these ever failed at sea the chances of repair would be limited.

My solution was to have a separate line rigged through the boom to the blue line shown in picture C which just sits in the lazy cover until required. This blue line goes under the boom & the end not hooked to the red & white line has a large knot. This is to stop it slipping out through the slot in the cover. If one does not have enough pullies in the boom for the extra line one can always swop to the clew outhaul provided it has a snap shackle & is long enough to lead back to a winch on the deck where a strong pull needs to be applied

To reef I drop the boom, I head into wind (start the engine for a few minutes if needs be) I release the topping lift & halyard (I know from experience how much to let off) I go forward & hook the strop to the sail spectacles & under the spinnaker ring as in picture B. This keeps the sail down enough to prevent not to crush the sliders below & stops the luff pulling aft away from the mast. Letting the topping lift off allows the boom to drop into the cockpit so I can safely rig the blue strop as shown in pictures D & E. In the picture it is not very tight but when the sail flogs a little overcoming friction. It will tighten a lot more pulling the clew out & down to give a nice flat sail or I can leave a fuller shape if I so wish. (It was just done lightly in a marina for the pictures.)

I then hoist the halyard, bear away & stop the engine.

An improvement would be a lighter leech strop with a plastic stopper instead of the clumsy looking knot & the strop at the mast could be a little shorter, but I have had this for years & it has always worked, so it remains on the “to do” list
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Thanks for the detailed reply, I don’t sail with a sail bag so that’s probably not the solution for me but otherwise some good points. I’m more than happy doing all the work at the mast and don’t want any more lines other than the topping lift going back to the cockpit.
 
We were/are in a similar position, like you all reefing done from the mast.
For a while we just kept the 2nd and 3rd reefs permanently rigged and didn't use the 1st reef or tied it down to the outhaul if we really wanted it.
Now we added a reefing line down the outside of the boom for the first reef.
This doesn't work as well as the internal lines as there is no jammer, but it works well enough.
This is rigged as follows:

Line terminated at outhaul
Runs up through the reefing eye and back down to the boom.
There is a pulley lashed to an eye we have in the side of the boom (this is normally where our reefing lines terminate, non loose footed sail).
This runs along the side of the boom inside our lazybag so it doesn't flap around.
Through A thimble (I don't have a friction ring at the time) lashed to the goose neck.
Down to a spare cleat on mast.
If needed I can run it round the reefing winch first if I need to get more tension.

I hope that's clear.
It would probably be nice with a cheek block on the boom and a jamber to lock it off.

Normally it's calm enough when putting in the first reef that it's easy enough to do.
And when putting in the next two as it gets winder and rough
 
Thanks, that sounds exactly like my current setup and makes a lot of sense so I think I will be making something over the winter. I really don’t want the hassle of pop-diverting new bits of kit onto the boom, but as it’s a loose footed main I’ve got more options to tie a block on.
We were/are in a similar position, like you all reefing done from the mast.
For a while we just kept the 2nd and 3rd reefs permanently rigged and didn't use the 1st reef or tied it down to the outhaul if we really wanted it.
Now we added a reefing line down the outside of the boom for the first reef.
This doesn't work as well as the internal lines as there is no jammer, but it works well enough.
This is rigged as follows:

Line terminated at outhaul
Runs up through the reefing eye and back down to the boom.
There is a pulley lashed to an eye we have in the side of the boom (this is normally where our reefing lines terminate, non loose footed sail).
This runs along the side of the boom inside our lazybag so it doesn't flap around.
Through A thimble (I don't have a friction ring at the time) lashed to the goose neck.
Down to a spare cleat on mast.
If needed I can run it round the reefing winch first if I need to get more tension.

I hope that's clear.
It would probably be nice with a cheek block on the boom and a jamber to lock it off.

Normally it's calm enough when putting in the first reef that it's easy enough to do.
And when putting in the next two as it gets winder and rough
 
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