That never worked for me, although I only tried it once; pulling on the Insulet syringe felt like I was trying to reel in the Midgard Serpent. For a while I dialed in the 150IU from the pen and used that to squirt the insulin into the Insulet syringe. Then I gave up and got pen needles long enough to inject directly into the syringe (6mm IRC). This works just fine but, like @Eric the vials are just so much easier. I have the 6mm for vacations.
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It will definitely become harder to do as he gets older and has more insulin requirements. We are still filling it with the minimum required for now.
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I am the same as you @ClaudnDaye . I was recently given a large amount of unwanted insulin pens - and guess what? I am using them (and they’re actually expired pens - and work just fine - but that’s a risk I take as someone with T1D for almost 60 years.
As someone who pays out of pocket for insulin here in Canada (my diabetes and other medical issues that have compromised me as a working stiff - I don’t qualify for disability which covers everything technology, medical, dental, etc. ). That 's socialised healthcare system in our various provinces that have different “handout” programs that tax payers pay into - sigh - #Pharmacare4all #Access4all - I’m an advocate in the diabetes world.
I do find, with not introducing air like we do into the vials for filling up the pump systems we use (I am currently using gifted expired Eros Omnipods - what a treat from tubed pumps that I “play” with for a change of pace as I’m sailing the great blue sea in a 2500 NM journey with this years diaversary) - that as someone has mentioned here in this thread - it’s actually a better choice. Just ensuring that you’re hands are clean, vial stopper is clean, yadda, yadda, yadda. You know the drill.
Main thing, whatever works for the individual. Keeping an eye on their BG’s if they go wonky for no explained reason (easier said than done with how 200+ variables can affect which way the roller coaster ride of diabetes goes).
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Great picture, @FatCatAnna ! 
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Thanks @Eric - sorry for the late reply . Back on terra ferma late September - and just trying to get used to land lubber life. I really think my blood sugars are better maintained while sailing - WHALE … and 35 knot gusts of winds out on the ocean - good stress - good stress - the boat can handle it - and so can the crew (moi et Captain). Even got an award from my sailing club for what I did this summer - they now know more about T1D than they ever did with all my public posts. Will leave you with this picture of SV Jenna’s Journey in Great Salt Pond, RI (while hiding away from ocean surge with one of the many hurricanes swirling up south) now in her cradle for the winter - until next May - then let the adventures begin again (changing out the rigging - she’s due a new set to keep the mast up).
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Good tip on the dialing up the units. I’m only seeing this now Finn - and kinda figured it out myself - like … cough cough … last week. I had to do a correction injection due to abit of overtly sweet eating (hey - we only do this once in a blue moon right? 
) … and now all good - incase I have to use the pen again - and it’s all primed set for a jab in the you know where!
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