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  #9  
Old 02-02-2009, 08:43 PM
Seth
Guest
 
Posts: n/a
Default Re: Dividing up proceeds between long-term and short-term portion ofa stock sale

In article <6d9987d8-e236-4de4-82d0-103d3e58587c[at]a12g2000pro.googlegroups.com> ,
Just a User <chance2now[at]gmail.com> wrote:

- quote -

> Here is where the issue comes up. I get one check for the whole sale.
> The question is, if I sell, say, 20 shares (purchased at different
> time for different amounts) and receive $1000 after sales fees, do I
> have to report that I received $50 for each share?


Yes.

- quote -

> Or can I assign this $1000 another way?

Almost certainly not. (If you instructed your broker to sell specific
lots at different times/prices, then you'd report actual proceeds for
each lot. But that's not the case.)

- quote -

> If all the shares cost a total of $950, for
> example, can I report a gain of $2.50 per share?


No.

Seth

--
<< ------------------------------------------------------- > << The foregoing was not intended or written to be used, > << nor can it used, for the purpose of avoiding penalties > << that may be imposed upon the taxpayer. > << > << The Charter and the Guidelines for submitting posts > << to this newsgroup as well as our anti-spamming policy > << are at www.asktax.org. > << Copyright (2007) - All rights reserved. > << ------------------------------------------------------- >
  #8  
Old 02-02-2009, 06:54 AM
Barry Margolin
Guest
 
Posts: n/a
Default Re: Dividing up proceeds between long-term and short-term portion of a stock sale

In article <gm3jd9$on9$2[at]snarked.org> ,
"D. Stussy" <spam[at]bde-arc.ampr.org> wrote:

- quote -

> "Barry Margolin" <barmar[at]alum.mit.edu> wrote in message
> news:barmar-BC8F62.21341231012009[at]mara100-84.onlink.net...
> > In article
> > <6d9987d8-e236-4de4-82d0-103d3e58587c[at]a12g2000pro.googlegroups.com> ,
> > Just a User <chance2now[at]gmail.com> wrote:
> > > > Here is where the issue comes up. I get one check for the whole sale.
> > > The question is, if I sell, say, 20 shares (purchased at different
> > > time for different amounts) and receive $1000 after sales fees, do I
> > > have to report that I received $50 for each share? Or can I assign
> > > If all the shares were sold for the same price, then you received $50

> > for each share.
> > > > this $1000 another way? If all the shares cost a total of $950, for
> > > example, can I report a gain of $2.50 per share? This would require
> > > distributing the proceeds of the sale to each share based on the cost
> > > of that share. I have tried to look on the IRS website for a rule
> > > pertaining to this, but it is hard to know exactly what to search for.
> > > Read publication 550. It says "Except for certain mutual fund shares,

> > discussed later, you cannot use the average price per share to figure
> > gain or loss on the sale of the shares."
> > > So if you purchased 10 shares for $350, and 10 shares for $600, you have

> > a gain of $150 on the first lot, and a loss of $100 on the second lot.
> > If you purchased another 5 shares within 30 days of the sale, you you
> > have a wash sale on 5 of the shares of the second lot, so you can only
> > report $50 of loss, and you add $50 to the cost basis of the new shares.

> Yes but in the OP's situation, he still recognizes the loss because the
> wash-sale reacquisition was itself sold. It washed out.


You keep on making up things that he never said. He wrote:

- quote -

> Of course, since this is an automatic payroll deduction, I continued
> to purchase shares after the sale, so I would have to answer yes to
> this.


These are the reacquisition shares, and he never said anything about
selling them.

--
Barry Margolin, barmar[at]alum.mit.edu
Arlington, MA
*** PLEASE don't copy me on replies, I'll read them in the group ***

--
<< ------------------------------------------------------- > << The foregoing was not intended or written to be used, > << nor can it used, for the purpose of avoiding penalties > << that may be imposed upon the taxpayer. > << > << The Charter and the Guidelines for submitting posts > << to this newsgroup as well as our anti-spamming policy > << are at www.asktax.org. > << Copyright (2007) - All rights reserved. > << ------------------------------------------------------- >
  #7  
Old 02-02-2009, 12:48 AM
D. Stussy
Guest
 
Posts: n/a
Default Re: Dividing up proceeds between long-term and short-term portion of a stock sale

"Barry Margolin" <barmar[at]alum.mit.edu> wrote in message
news:barmar-BC8F62.21341231012009[at]mara100-84.onlink.net...
- quote -

> In article
> <6d9987d8-e236-4de4-82d0-103d3e58587c[at]a12g2000pro.googlegroups.com> ,
> Just a User <chance2now[at]gmail.com> wrote:
> > Here is where the issue comes up. I get one check for the whole sale.
> > The question is, if I sell, say, 20 shares (purchased at different
> > time for different amounts) and receive $1000 after sales fees, do I
> > have to report that I received $50 for each share? Or can I assign

> If all the shares were sold for the same price, then you received $50
> for each share.
> > this $1000 another way? If all the shares cost a total of $950, for
> > example, can I report a gain of $2.50 per share? This would require
> > distributing the proceeds of the sale to each share based on the cost
> > of that share. I have tried to look on the IRS website for a rule
> > pertaining to this, but it is hard to know exactly what to search for.

> Read publication 550. It says "Except for certain mutual fund shares,
> discussed later, you cannot use the average price per share to figure
> gain or loss on the sale of the shares."
> So if you purchased 10 shares for $350, and 10 shares for $600, you have
> a gain of $150 on the first lot, and a loss of $100 on the second lot.
> If you purchased another 5 shares within 30 days of the sale, you you
> have a wash sale on 5 of the shares of the second lot, so you can only
> report $50 of loss, and you add $50 to the cost basis of the new shares.


Yes but in the OP's situation, he still recognizes the loss because the
wash-sale reacquisition was itself sold. It washed out.

--
<< ------------------------------------------------------- > << The foregoing was not intended or written to be used, > << nor can it used, for the purpose of avoiding penalties > << that may be imposed upon the taxpayer. > << > << The Charter and the Guidelines for submitting posts > << to this newsgroup as well as our anti-spamming policy > << are at www.asktax.org. > << Copyright (2007) - All rights reserved. > << ------------------------------------------------------- >
  #6  
Old 02-01-2009, 01:34 AM
Barry Margolin
Guest
 
Posts: n/a
Default Re: Dividing up proceeds between long-term and short-term portion of a stock sale

In article
<6d9987d8-e236-4de4-82d0-103d3e58587c[at]a12g2000pro.googlegroups.com> ,
Just a User <chance2now[at]gmail.com> wrote:

- quote -

> Here is where the issue comes up. I get one check for the whole sale.
> The question is, if I sell, say, 20 shares (purchased at different
> time for different amounts) and receive $1000 after sales fees, do I
> have to report that I received $50 for each share? Or can I assign


If all the shares were sold for the same price, then you received $50
for each share.

- quote -

> this $1000 another way? If all the shares cost a total of $950, for
> example, can I report a gain of $2.50 per share? This would require
> distributing the proceeds of the sale to each share based on the cost
> of that share. I have tried to look on the IRS website for a rule
> pertaining to this, but it is hard to know exactly what to search for.


Read publication 550. It says "Except for certain mutual fund shares,
discussed later, you cannot use the average price per share to figure
gain or loss on the sale of the shares."

So if you purchased 10 shares for $350, and 10 shares for $600, you have
a gain of $150 on the first lot, and a loss of $100 on the second lot.
If you purchased another 5 shares within 30 days of the sale, you you
have a wash sale on 5 of the shares of the second lot, so you can only
report $50 of loss, and you add $50 to the cost basis of the new shares.

--
Barry Margolin, barmar[at]alum.mit.edu
Arlington, MA
*** PLEASE don't copy me on replies, I'll read them in the group ***

--
<< ------------------------------------------------------- > << The foregoing was not intended or written to be used, > << nor can it used, for the purpose of avoiding penalties > << that may be imposed upon the taxpayer. > << > << The Charter and the Guidelines for submitting posts > << to this newsgroup as well as our anti-spamming policy > << are at www.asktax.org. > << Copyright (2007) - All rights reserved. > << ------------------------------------------------------- >
  #5  
Old 01-31-2009, 07:48 PM
Just a User
Guest
 
Posts: n/a
Default Re: Dividing up proceeds between long-term and short-term portion ofa stock sale

On Jan 31, 1:42*pm, Barry Margolin <bar...[at]alum.mit.edu> wrote:
- quote -

> In article <gm110p$a5...[at]snarked.org> ,
> *"D. Stussy" <s...[at]bde-arc.ampr.org> wrote:
> > I need a better explanation of the transactions before I can agree with
> > that. *He said that the price of the stock was increasing, so his sales
> > should always be at a gain. *Therefore, there's no wash sales. *Even if one
> > lot is at a loss, it has other purchases in adjacent pay periods that are
> > gains that wash it out.

> He wrote: "The issue that I came up against is that, because the
> short-term shares tended to cost more, this results in a short-term
> loss and a long-term gain." *So the price was generally trending up in
> the long run, but dropped a bit before he sold, so the recent shares
> were sold at losses.


Yes, that is part of the reason; also, there are fees associated with
the sale which make it harder to sell the more recent shares for a
gain. The loss is actually very small in relation to the total sale,
but it is a loss nonetheless.

- quote -

> Since he automatically purchased more shares 2 and 4 weeks later, some
> of those sales (up to the number of shares he repurchased) become wash
> sales. *He can't take the loss now, he has to add the disallowed losses
> to the cost basis of the new shares. *So his eventual capital gain is
> reduced (or his eventual capital loss increased) when he later sells
> those new shares.
> In order to ignore the wash sale rule completely, you have to sell all
> shares of the security, and not buy any new shares for 30 days. *Or
> don't sell any of the lots that have losses -- it doesn't matter whether
> you have a net gain in total.


Here is where the issue comes up. I get one check for the whole sale.
The question is, if I sell, say, 20 shares (purchased at different
time for different amounts) and receive $1000 after sales fees, do I
have to report that I received $50 for each share? Or can I assign
this $1000 another way? If all the shares cost a total of $950, for
example, can I report a gain of $2.50 per share? This would require
distributing the proceeds of the sale to each share based on the cost
of that share. I have tried to look on the IRS website for a rule
pertaining to this, but it is hard to know exactly what to search for.

Thanks for all the responses so far.

--
<< ------------------------------------------------------- > << The foregoing was not intended or written to be used, > << nor can it used, for the purpose of avoiding penalties > << that may be imposed upon the taxpayer. > << > << The Charter and the Guidelines for submitting posts > << to this newsgroup as well as our anti-spamming policy > << are at www.asktax.org. > << Copyright (2007) - All rights reserved. > << ------------------------------------------------------- >
  #4  
Old 01-31-2009, 05:42 PM
Barry Margolin
Guest
 
Posts: n/a
Default Re: Dividing up proceeds between long-term and short-term portion of a stock sale

In article <gm110p$a56$1[at]snarked.org> ,
"D. Stussy" <spam[at]bde-arc.ampr.org> wrote:

- quote -

> I need a better explanation of the transactions before I can agree with
> that. He said that the price of the stock was increasing, so his sales
> should always be at a gain. Therefore, there's no wash sales. Even if one
> lot is at a loss, it has other purchases in adjacent pay periods that are
> gains that wash it out.


He wrote: "The issue that I came up against is that, because the
short-term shares tended to cost more, this results in a short-term
loss and a long-term gain." So the price was generally trending up in
the long run, but dropped a bit before he sold, so the recent shares
were sold at losses.

Since he automatically purchased more shares 2 and 4 weeks later, some
of those sales (up to the number of shares he repurchased) become wash
sales. He can't take the loss now, he has to add the disallowed losses
to the cost basis of the new shares. So his eventual capital gain is
reduced (or his eventual capital loss increased) when he later sells
those new shares.

In order to ignore the wash sale rule completely, you have to sell all
shares of the security, and not buy any new shares for 30 days. Or
don't sell any of the lots that have losses -- it doesn't matter whether
you have a net gain in total.

--
Barry Margolin, barmar[at]alum.mit.edu
Arlington, MA
*** PLEASE don't copy me on replies, I'll read them in the group ***

--
<< ------------------------------------------------------- > << The foregoing was not intended or written to be used, > << nor can it used, for the purpose of avoiding penalties > << that may be imposed upon the taxpayer. > << > << The Charter and the Guidelines for submitting posts > << to this newsgroup as well as our anti-spamming policy > << are at www.asktax.org. > << Copyright (2007) - All rights reserved. > << ------------------------------------------------------- >
  #3  
Old 01-31-2009, 05:23 PM
D. Stussy
Guest
 
Posts: n/a
Default Re: Dividing up proceeds between long-term and short-term portion of a stock sale

"Barry Margolin" <barmar[at]alum.mit.edu> wrote in message
news:barmar-3FD4A2.21571330012009[at]mara100-84.onlink.net...
- quote -

> In article <gm06n4$sdj$10[at]snarked.org> ,
> "D. Stussy" <spam[at]bde-arc.ampr.org> wrote:
> > "Barry Margolin" <barmar[at]alum.mit.edu> wrote in message
> > news:barmar-E6DF34.21491429012009[at]mara100-84.onlink.net...
> > > In article
> > > <0d364376-8901-42ed-a76b-9a4bf5de06f0[at]w1g2000prm.googlegroups.com> ,
> > > Just a User <chance2now[at]gmail.com> wrote:
> > > > > > Greetings all.
> > > > > > > I am attempting to report a stock sale which happened during 2008.

It
> > > > is a sale from an Employee Stock Plan, so it consists of multiple
> > > > purchases made every two weeks over time. There is a short-term and

a
> > > > long-term portion of the sale. Because the stock value was

generally
> > > > rising before I sold it, the short-term shares tend to have a

higher
> > > > cost than the long-term shares.
> > > > > Did they really purchase shares every 2 weeks? I've participated in

a
> > > number of ESOPs, and they all worked by taking cash from my paycheck
> > > every pay period, but they only purchased the company stock once

every 6
> > > months.
> > > > > > > > > I received a 1099-B which reported the total proceeds from the

sale.
> > > > In order to report this sale, I have to divide it up into two

sales,
> > > > one for the short-term shares and one for the long-term shares.

This
> > > > means that I have to divide up the proceeds between the two "sub-
> > > > sales". The most natural way to divide this up seemed to be to

weight
> > > > it according to the number of shares involved in each "sub-sale";
> > > > i.e., short_term_proceeds = total_proceeds X short_term_shares /
> > > > total_shares and long_term_proceeds = total_proceeds X
> > > > long_term_shares / total_shares.
> > > > > > > The issue that I came up against is that, because the short-term
> > > > shares tended to cost more, this results in a short-term loss and a
> > > > long-term gain. I tried to enter these figures (I am using

TurboTax's
> > > > free online filing), and when I put in the short-term portion, it
> > > > follows up by warning me that this sale may be subject to "wash

sale
> > > > rules" and asks me if I then purchased substantially similar

shares.
> > > > Of course, since this is an automatic payroll deduction, I

continued
> > > > to purchase shares after the sale, so I would have to answer yes to
> > > > this.
> > > > > > > Since I don't really think that I should be declaring a loss on

this
> > > > sale (because the sale resulted in an overall gain), I then

wondered
> > > > > It doesn't matter whether there's an overall gain. You have to
> > > calculate the gain or loss for each lot you purchased. TurboTax is
> > > correct: if some of them were losses, the losses have to be deferred
> > > because of the wash sale rules.
> > > But it's not a wash sale. The holding periods were in parallel. It

wasn't
> > a sale then buy-back because there was no buy-back.

> That doesn't matter. It's a wash sale if you purchased shares of the
> same company within 30 days BEFORE OR AFTER the sale. He purchased
> shares 4 weeks before, 2 weeks before, that same week, 2 weeks later,
> and 4 weeks later -- all of those are within the 30 day window
> (actually, depending on the day of the week of the sale, the first or
> last is probably outside the window).


As for the purchases 2 and 4 weeks earlier, he sold those too - so the wash
sale washes out.

- quote -

> > Even if there were a wash sale in there, since he disposed of ALL of
the
> > stock, the wash sale washes out.

> He never said he sold all his shares, but maybe it was implied by his
> attempt to average everything. But even if he did, he purchased shares
> 2 and 4 weeks later -- those count as buy-backs, and will cause the wash
> sale rule to apply.


I need a better explanation of the transactions before I can agree with
that. He said that the price of the stock was increasing, so his sales
should always be at a gain. Therefore, there's no wash sales. Even if one
lot is at a loss, it has other purchases in adjacent pay periods that are
gains that wash it out.

--
<< ------------------------------------------------------- > << The foregoing was not intended or written to be used, > << nor can it used, for the purpose of avoiding penalties > << that may be imposed upon the taxpayer. > << > << The Charter and the Guidelines for submitting posts > << to this newsgroup as well as our anti-spamming policy > << are at www.asktax.org. > << Copyright (2007) - All rights reserved. > << ------------------------------------------------------- >
  #2  
Old 01-31-2009, 01:57 AM
Barry Margolin
Guest
 
Posts: n/a
Default Re: Dividing up proceeds between long-term and short-term portion of a stock sale

In article <gm06n4$sdj$10[at]snarked.org> ,
"D. Stussy" <spam[at]bde-arc.ampr.org> wrote:

- quote -

> "Barry Margolin" <barmar[at]alum.mit.edu> wrote in message
> news:barmar-E6DF34.21491429012009[at]mara100-84.onlink.net...
> > In article
> > <0d364376-8901-42ed-a76b-9a4bf5de06f0[at]w1g2000prm.googlegroups.com> ,
> > Just a User <chance2now[at]gmail.com> wrote:
> > > > Greetings all.
> > > > > I am attempting to report a stock sale which happened during 2008. It
> > > is a sale from an Employee Stock Plan, so it consists of multiple
> > > purchases made every two weeks over time. There is a short-term and a
> > > long-term portion of the sale. Because the stock value was generally
> > > rising before I sold it, the short-term shares tend to have a higher
> > > cost than the long-term shares.
> > > Did they really purchase shares every 2 weeks? I've participated in a

> > number of ESOPs, and they all worked by taking cash from my paycheck
> > every pay period, but they only purchased the company stock once every 6
> > months.
> > > > > > I received a 1099-B which reported the total proceeds from the sale.
> > > In order to report this sale, I have to divide it up into two sales,
> > > one for the short-term shares and one for the long-term shares. This
> > > means that I have to divide up the proceeds between the two "sub-
> > > sales". The most natural way to divide this up seemed to be to weight
> > > it according to the number of shares involved in each "sub-sale";
> > > i.e., short_term_proceeds = total_proceeds X short_term_shares /
> > > total_shares and long_term_proceeds = total_proceeds X
> > > long_term_shares / total_shares.
> > > > > The issue that I came up against is that, because the short-term
> > > shares tended to cost more, this results in a short-term loss and a
> > > long-term gain. I tried to enter these figures (I am using TurboTax's
> > > free online filing), and when I put in the short-term portion, it
> > > follows up by warning me that this sale may be subject to "wash sale
> > > rules" and asks me if I then purchased substantially similar shares.
> > > Of course, since this is an automatic payroll deduction, I continued
> > > to purchase shares after the sale, so I would have to answer yes to
> > > this.
> > > > > Since I don't really think that I should be declaring a loss on this
> > > sale (because the sale resulted in an overall gain), I then wondered
> > > It doesn't matter whether there's an overall gain. You have to

> > calculate the gain or loss for each lot you purchased. TurboTax is
> > correct: if some of them were losses, the losses have to be deferred
> > because of the wash sale rules.

> But it's not a wash sale. The holding periods were in parallel. It wasn't
> a sale then buy-back because there was no buy-back.


That doesn't matter. It's a wash sale if you purchased shares of the
same company within 30 days BEFORE OR AFTER the sale. He purchased
shares 4 weeks before, 2 weeks before, that same week, 2 weeks later,
and 4 weeks later -- all of those are within the 30 day window
(actually, depending on the day of the week of the sale, the first or
last is probably outside the window).

- quote -

> Even if there were a wash sale in there, since he disposed of ALL of the
> stock, the wash sale washes out.


He never said he sold all his shares, but maybe it was implied by his
attempt to average everything. But even if he did, he purchased shares
2 and 4 weeks later -- those count as buy-backs, and will cause the wash
sale rule to apply.

--
Barry Margolin, barmar[at]alum.mit.edu
Arlington, MA
*** PLEASE don't copy me on replies, I'll read them in the group ***

--
<< ------------------------------------------------------- > << The foregoing was not intended or written to be used, > << nor can it used, for the purpose of avoiding penalties > << that may be imposed upon the taxpayer. > << > << The Charter and the Guidelines for submitting posts > << to this newsgroup as well as our anti-spamming policy > << are at www.asktax.org. > << Copyright (2007) - All rights reserved. > << ------------------------------------------------------- >
  #1  
Old 01-30-2009, 11:43 PM
D. Stussy
Guest
 
Posts: n/a
Default Re: Dividing up proceeds between long-term and short-term portion of a stock sale

"Barry Margolin" <barmar[at]alum.mit.edu> wrote in message
news:barmar-E6DF34.21491429012009[at]mara100-84.onlink.net...
- quote -

> In article
> <0d364376-8901-42ed-a76b-9a4bf5de06f0[at]w1g2000prm.googlegroups.com> ,
> Just a User <chance2now[at]gmail.com> wrote:
> > Greetings all.
> > > I am attempting to report a stock sale which happened during 2008. It

> > is a sale from an Employee Stock Plan, so it consists of multiple
> > purchases made every two weeks over time. There is a short-term and a
> > long-term portion of the sale. Because the stock value was generally
> > rising before I sold it, the short-term shares tend to have a higher
> > cost than the long-term shares.

> Did they really purchase shares every 2 weeks? I've participated in a
> number of ESOPs, and they all worked by taking cash from my paycheck
> every pay period, but they only purchased the company stock once every 6
> months.
> > > I received a 1099-B which reported the total proceeds from the sale.

> > In order to report this sale, I have to divide it up into two sales,
> > one for the short-term shares and one for the long-term shares. This
> > means that I have to divide up the proceeds between the two "sub-
> > sales". The most natural way to divide this up seemed to be to weight
> > it according to the number of shares involved in each "sub-sale";
> > i.e., short_term_proceeds = total_proceeds X short_term_shares /
> > total_shares and long_term_proceeds = total_proceeds X
> > long_term_shares / total_shares.
> > > The issue that I came up against is that, because the short-term

> > shares tended to cost more, this results in a short-term loss and a
> > long-term gain. I tried to enter these figures (I am using TurboTax's
> > free online filing), and when I put in the short-term portion, it
> > follows up by warning me that this sale may be subject to "wash sale
> > rules" and asks me if I then purchased substantially similar shares.
> > Of course, since this is an automatic payroll deduction, I continued
> > to purchase shares after the sale, so I would have to answer yes to
> > this.
> > > Since I don't really think that I should be declaring a loss on this

> > sale (because the sale resulted in an overall gain), I then wondered

> It doesn't matter whether there's an overall gain. You have to
> calculate the gain or loss for each lot you purchased. TurboTax is
> correct: if some of them were losses, the losses have to be deferred
> because of the wash sale rules.


But it's not a wash sale. The holding periods were in parallel. It wasn't
a sale then buy-back because there was no buy-back.

Even if there were a wash sale in there, since he disposed of ALL of the
stock, the wash sale washes out.

- quote -

> > if I should declare my short-term proceeds to be equal to my short-
> > term cost basis, and assign the remainder to the long-term portion. Or
> > possibly I should assign them so that I report both a short-term and
> > long-term gain, and weight the gain according to the number of shares
> > involved, similar to what I attempted to do in weighting the proceeds.
> > > Is anyone aware of an IRS requirement to use a particular method to

> > assign the proceeds from this sale? If so, please point me to the
> > relevant area on the IRS site. If the IRS does not require a
> > particular method, can you recommend the one I should use? I
> > appreciate any assistance anyone can provide.

> For regular stock, there's no averaging method allowed. For mutual
> funds you can average, although I think you still have to adjust for
> wash sales -- there's no way around the wash sale rule.


The wash sale rule doesn't apply in the first place.

--
<< ------------------------------------------------------- > << The foregoing was not intended or written to be used, > << nor can it used, for the purpose of avoiding penalties > << that may be imposed upon the taxpayer. > << > << The Charter and the Guidelines for submitting posts > << to this newsgroup as well as our anti-spamming policy > << are at www.asktax.org. > << Copyright (2007) - All rights reserved. > << ------------------------------------------------------- >
 
Old 01-30-2009, 01:49 AM
Barry Margolin
Guest
 
Posts: n/a
Default Re: Dividing up proceeds between long-term and short-term portion of a stock sale

In article
<0d364376-8901-42ed-a76b-9a4bf5de06f0[at]w1g2000prm.googlegroups.com> ,
Just a User <chance2now[at]gmail.com> wrote:

- quote -

> Greetings all.
> I am attempting to report a stock sale which happened during 2008. It
> is a sale from an Employee Stock Plan, so it consists of multiple
> purchases made every two weeks over time. There is a short-term and a
> long-term portion of the sale. Because the stock value was generally
> rising before I sold it, the short-term shares tend to have a higher
> cost than the long-term shares.


Did they really purchase shares every 2 weeks? I've participated in a
number of ESOPs, and they all worked by taking cash from my paycheck
every pay period, but they only purchased the company stock once every 6
months.

- quote -

> I received a 1099-B which reported the total proceeds from the sale.
> In order to report this sale, I have to divide it up into two sales,
> one for the short-term shares and one for the long-term shares. This
> means that I have to divide up the proceeds between the two "sub-
> sales". The most natural way to divide this up seemed to be to weight
> it according to the number of shares involved in each "sub-sale";
> i.e., short_term_proceeds = total_proceeds X short_term_shares /
> total_shares and long_term_proceeds = total_proceeds X
> long_term_shares / total_shares.
> The issue that I came up against is that, because the short-term
> shares tended to cost more, this results in a short-term loss and a
> long-term gain. I tried to enter these figures (I am using TurboTax's
> free online filing), and when I put in the short-term portion, it
> follows up by warning me that this sale may be subject to "wash sale
> rules" and asks me if I then purchased substantially similar shares.
> Of course, since this is an automatic payroll deduction, I continued
> to purchase shares after the sale, so I would have to answer yes to
> this.
> Since I don't really think that I should be declaring a loss on this
> sale (because the sale resulted in an overall gain), I then wondered


It doesn't matter whether there's an overall gain. You have to
calculate the gain or loss for each lot you purchased. TurboTax is
correct: if some of them were losses, the losses have to be deferred
because of the wash sale rules.

- quote -

> if I should declare my short-term proceeds to be equal to my short-
> term cost basis, and assign the remainder to the long-term portion. Or
> possibly I should assign them so that I report both a short-term and
> long-term gain, and weight the gain according to the number of shares
> involved, similar to what I attempted to do in weighting the proceeds.
> Is anyone aware of an IRS requirement to use a particular method to
> assign the proceeds from this sale? If so, please point me to the
> relevant area on the IRS site. If the IRS does not require a
> particular method, can you recommend the one I should use? I
> appreciate any assistance anyone can provide.


For regular stock, there's no averaging method allowed. For mutual
funds you can average, although I think you still have to adjust for
wash sales -- there's no way around the wash sale rule.

--
Barry Margolin, barmar[at]alum.mit.edu
Arlington, MA
*** PLEASE don't copy me on replies, I'll read them in the group ***

--
<< ------------------------------------------------------- > << The foregoing was not intended or written to be used, > << nor can it used, for the purpose of avoiding penalties > << that may be imposed upon the taxpayer. > << > << The Charter and the Guidelines for submitting posts > << to this newsgroup as well as our anti-spamming policy > << are at www.asktax.org. > << Copyright (2007) - All rights reserved. > << ------------------------------------------------------- >
  #-1  
Old 01-30-2009, 01:13 AM
Just a User
Guest
 
Posts: n/a
Default Dividing up proceeds between long-term and short-term portion of astock sale

Greetings all.

I am attempting to report a stock sale which happened during 2008. It
is a sale from an Employee Stock Plan, so it consists of multiple
purchases made every two weeks over time. There is a short-term and a
long-term portion of the sale. Because the stock value was generally
rising before I sold it, the short-term shares tend to have a higher
cost than the long-term shares.

I received a 1099-B which reported the total proceeds from the sale.
In order to report this sale, I have to divide it up into two sales,
one for the short-term shares and one for the long-term shares. This
means that I have to divide up the proceeds between the two "sub-
sales". The most natural way to divide this up seemed to be to weight
it according to the number of shares involved in each "sub-sale";
i.e., short_term_proceeds = total_proceeds X short_term_shares /
total_shares and long_term_proceeds = total_proceeds X
long_term_shares / total_shares.

The issue that I came up against is that, because the short-term
shares tended to cost more, this results in a short-term loss and a
long-term gain. I tried to enter these figures (I am using TurboTax's
free online filing), and when I put in the short-term portion, it
follows up by warning me that this sale may be subject to "wash sale
rules" and asks me if I then purchased substantially similar shares.
Of course, since this is an automatic payroll deduction, I continued
to purchase shares after the sale, so I would have to answer yes to
this.

Since I don't really think that I should be declaring a loss on this
sale (because the sale resulted in an overall gain), I then wondered
if I should declare my short-term proceeds to be equal to my short-
term cost basis, and assign the remainder to the long-term portion. Or
possibly I should assign them so that I report both a short-term and
long-term gain, and weight the gain according to the number of shares
involved, similar to what I attempted to do in weighting the proceeds.

Is anyone aware of an IRS requirement to use a particular method to
assign the proceeds from this sale? If so, please point me to the
relevant area on the IRS site. If the IRS does not require a
particular method, can you recommend the one I should use? I
appreciate any assistance anyone can provide.

Tom

--
<< ------------------------------------------------------- > << The foregoing was not intended or written to be used, > << nor can it used, for the purpose of avoiding penalties > << that may be imposed upon the taxpayer. > << > << The Charter and the Guidelines for submitting posts > << to this newsgroup as well as our anti-spamming policy > << are at www.asktax.org. > << Copyright (2007) - All rights reserved. > << ------------------------------------------------------- >
 

Tags
astock, dividing, longterm, portion, proceeds, sale, shortterm
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