user109: Most advanced players know when it is time to resign, but many beginners don't.  What factors do you consider when it is time to resign?

user7147: For me, it really depends on the situation, and my opponent.  If my opponent is skilled (or at least, better than me...), and even I can see that my opponent has a clear (though possibly not immediate) win and that it's just a matter of grinding it out, I'll normally resign.  It saves us both a lot of fatigue and time, and I can use the extra time to go outside the tournament site and go get something to eat.  ;-)
If my opponent is more around my own level, and my own situation isn't utterly hopeless, I'll wait longer to resign, because you never know when the opponent is going to blunder.  The winner of any chess game is whoever makes the next to the last mistake...  I've played out (and won) a number of games in this type of situation, where I'm down a couple pieces plus maybe a few pawns in the middle game, and my opponent just "out of the blue" hangs their queen or something.
If I see that my opponent is in the process of executing a particularly pretty checkmate, I'll play it out.  They worked for it, they deserve to see it played out on the board, and they deserve to take home a scoresheet with the complete checkmate sequence on it.
One situation I never resign in, though, is when my opponent has a massive material advantage, such as multiple pieces against either a bare king, or against a bare king and maybe a few pawns.  At this point, I'll start trying to drive towards stalemate.  My assumption is if my opponent has that much of a material advantage and I'm still not checkmated, they may not actually have a plan, and they may not be paying a lot of attention to stalemate possibilities.  I have managed to "steal" half a point out of games like this on a number of occasions.

user7726: All the above answers refer to individual tournaments, but in a team what has happened or is happening on other boards might affect your decision. Admittedly it's more likely to affect what happens when a draw is offered, but you could play on if a draw, however unlikely, rather than a loss was of major benefit to the team as a whole.

user11245: It all depends on whether you can confidently expect your opponent to pursue the win to completion competently. Of course, the higher rated the players are, the more likely this is. At the club level, blunders happen frequently.
But even at the highest levels of play, it can happen that the opponent missteps.  Here's an example of a stunning upset from the Women's Olympiad, Baku 2016 that just finished. White's ELO: 1932. Black's: 2252 (That's a 320 ELO difference)...
[FEN ""]
[Event "Women's Baku Chess Olympiad"]
[Site "chess24.com"]
[Date "2016.09.13"]
[Round "11.1"]
[White "Shabanaj, Eglantina"]
[Black "Milovic, Aleksandra"]
[Result "1-0"]
[WhiteElo "1932"]
[BlackElo "2252"]

1. d4 Nf6 2. Nf3 e6 3. e3 b6 4. Bd3 Bb7 5. Nbd2 c5 6. c3 Nc6 7. O-O d5 8. dxc5 Bxc5 9. e4 O-O 10. Qe2 dxe4 11. Nxe4 Be7 12. Bg5 Nxe4 13. Qxe4 g6 14. Bh6 Re8 15. Rad1 Qc7 16. Bf4 Bd6 17. Bxd6 Qxd6 18. Qh4 Qe7 19. Ng5 h5 20. Rfe1 Kg7 21. Re3 Rad8 22. Qg3 Qd6 23. f4 Ne7? {+/- 3.26} 24. Rde1? {(=, -0.05) gives away the advantage} (24. Nxf7! {was correct} Kxf7 25. Bxg6+ Nxg6 26. Rxd6 Rxd6 27. f5 e5!? 28. fxg6+ Rxg6 29. Qf2+ Kg7 30. g3 Rf6 {+/- 3.38}) 24... Nd5?? {(-/+, -9.72) An unfortunate choice. In fact, a howler. Almost any other black move is better, including} (24... Bc6) (24... Rf8) (24... Bd5 {, or}) (24... Qc6) 25. Nxf7! {destruction with tempo} Kxf7? {Now it's mate in 5.} (25... Qxf4!? {(+/-, 11.67)} 26. Qxg6+ Kf8 27. Rf3 {is also winning}) 26. Qxg6+ Kf8 27. Qh6+ Kf7 28. Bg6+ Kf6 29. Bxe8+ (29. Bxh5+ {is faster, but the text works fine.} ) 1-0

For an example of how this question of "when to resign" plays out (no pun intended) at the GM level, see my response to the question "Is it possible to force checkmate with King, knight, and Bishop vs. King? (It is, of course, but apparently some GM's still want their opponents to prove it...).

user8860: "No game was ever won by resigning." -Tartakover
If playing on the team of opponents in a timed simultaneous exhibit,
resigning makes it easier on the exhibitor and thus harder on your teammates.
Thus one is often advised to never resign in this setting: even if your position
is hopeless, you may still help your teammates by forcing the exhibitor to actually win it.  Then again, some may regard this advice as unsportsmanlike.

user4418: I take 3 things into consideration when thinking about resigning:
1) The position on the clocks
2) The position on the board
3) The relative strength of my opponent
First off, if either I or my opponent are down to the last 2 minutes on the clock then I usually play on unless I'm really staring down the barrel. Something might happen and if it is disrespectful or masochistic it is only for another couple of minutes.
A concrete example of this the other way round happened to me a couple of years ago. I was winning comfortably (much better position plus an exchange and 2 pawns up) against a player rated about 200 points stronger than me. But, and it's a big but, I had 5 minutes left and he had 50 minutes. He played on, naturally, and with his extra time and the pressure I felt to try and win he managed to win.
Another player I know who has been within 50 ratings points of me for most of the last 15 years always used to resign the move before checkmate regardless of the situation or opponent. I found this deeply disrespectful and on one occasion about 12 years ago tried to teach him a lesson. I got a comfortable material advantage to the extent that I could do pretty much what I wanted. I still had 5 pawns left at this stage and implemented the following plan. 
I won all his remaining pawns and then started advancing my 5 connected pawns up the board as a unit. Once I had 5 pawns on the 7th rank I started queening them with the intention of ending up with 5 queens on the board if possible. He resigned after I queened the third pawn and explained to me that he was resigning because I had a mate in 3. I counter explained that I wasn't interested in mate until I'd queened all 5 pawns (in case he hadn't guessed).
He appeared at the time to be completely unaffected by this although maybe other, more blunt, folk had a word with him because the last time I beat him he resigned in an endgame a pawn down when I was 2 or 3 moves from queening a pawn.
I've never lost to a player more than 200 points lower than me (due as much as anything to lack of opportunity) but when I beat a master rated about 500 points higher than me he resigned 3 or 4 moves before an inevitable checkmate. Fair enough, I think.
At the other extreme about 10 years ago playing a player about 200 points stronger than me I was completely outplayed in the opening and middlegame and as his threats mounted I found myself losing the exchange. 
To his surprise I resigned. Why didn't I play on, he wanted to know, I was only an exchange down. The problem, I explained to him, was that before I lost the exchange I had a desperate position and after I lost the exchange I still had a desperate position only now I was an exchange down and within a few moves more material was going to follow and I would still be in a desperate position. He seemed disappointed, the sadist!
On the other hand I have several times against stronger opposition had the experience during the postmortem after a loss finding out that my opponent and I both had the impression that we were winning until quite late in the game, mistakenly on my part, obviously. They may very well have felt that I could have resigned sooner. Unfortunately my ability to evaluate the position accurately wasn't good enough to know that I was losing and should have resigned! If it had been I wouldn't have got into that position in the first place.

user17: The right time to resign is when you are have a disadvantage that is so large that you will reasonably expect to lose. This depends on your strength, and that of your opponent.
Between masters or higher, if one is behind by a clear pawn or more without positional or other compensation, it might be time to resign. On the other hand, as between beginners, even a piece behind might not call for a resignation, because the other beginner might easily lose it back.

user35: I was able to draw or even win some games I considered "clearly lost", especially if the opponent needed to know some theory (knight and bishop ending, Lucena and Philidor positions, opposition rules...). Consider the possibility of stalemate, or draw by repetition, too. This is often unexpected for the opponent, especially as you may launch a kamikaze attack and sacrifice lots of material in these cases.

user167: The right time to resign will vary from player to player, even if facing identical losing positions. But basically, the right time to resign is when, despite serious contemplation and effort of thought, you are convinced that there is simply no way to avoid a loss, and in addition you have lost all desire to play the position out. That said, there is nothing more frustrating than resigning prematurely, and a saying I've heard before goes something like "It's better to resign one move too late than one move too early," or "It's never too late to resign."
Some players can feel disrespected if an opponent plays on in what the first player considers a clearly lost position. But of course what one person can see clearly, others sometimes can't (or, not unlike the link above, the player who thinks it is already won might be mistaken). A player has every right to play until the bitter end every game without resigning -- these times can even be great learning experiences, seeing how one's opponent goes about winning a won position -- and I believe it is never disrespectful to do so, provided that the player on the losing end isn't, say, just running out the clock, motivated only by a desire to be annoying and waste the opponent's time.

109: <p>Most advanced players know when it is time to resign, but many beginners don't.  What factors do you consider when it is time to resign?</p>
 7147: <p>For me, it really depends on the situation, and my opponent.  If my opponent is skilled (or at least, better than me...), and even I can see that my opponent has a clear (though possibly not immediate) win and that it's just a matter of grinding it out, I'll normally resign.  It saves us both a lot of fatigue and time, and I can use the extra time to go outside the tournament site and go get something to eat.  ;-)</p>

<p>If my opponent is more around my own level, and my own situation isn't utterly hopeless, I'll wait longer to resign, because you never know when the opponent is going to blunder.  The winner of any chess game is whoever makes the next to the last mistake...  I've played out (and won) a number of games in this type of situation, where I'm down a couple pieces plus maybe a few pawns in the middle game, and my opponent just "out of the blue" hangs their queen or something.</p>

<p>If I see that my opponent is in the process of executing a particularly pretty checkmate, I'll play it out.  They worked for it, they deserve to see it played out on the board, and they deserve to take home a scoresheet with the complete checkmate sequence on it.</p>

<p>One situation I <em>never</em> resign in, though, is when my opponent has a massive material advantage, such as multiple pieces against either a bare king, or against a bare king and maybe a few pawns.  At this point, I'll start trying to drive towards stalemate.  My assumption is if my opponent has that much of a material advantage and I'm still not checkmated, they may not actually have a plan, and they may not be paying a lot of attention to stalemate possibilities.  I have managed to "steal" half a point out of games like this on a number of occasions.</p>
 7726: <p>All the above answers refer to individual tournaments, but in a team what has happened or is happening on other boards might affect your decision. Admittedly it's more likely to affect what happens when a draw is offered, but you could play on if a draw, however unlikely, rather than a loss was of major benefit to the team as a whole.</p>
 11245: <p>It all depends on whether you can confidently expect your opponent to pursue the win to completion competently. Of course, the higher rated the players are, the more likely this is. At the club level, blunders happen frequently.</p>

<p>But even at the highest levels of play, it can happen that the opponent missteps.  Here's an example of a stunning upset from the Women's Olympiad, Baku 2016 that just finished. White's ELO: 1932. Black's: 2252 (That's a <strong><em>320 ELO difference</em></strong>)...</p>

<pre><code>[FEN ""]
[Event "Women's Baku Chess Olympiad"]
[Site "chess24.com"]
[Date "2016.09.13"]
[Round "11.1"]
[White "Shabanaj, Eglantina"]
[Black "Milovic, Aleksandra"]
[Result "1-0"]
[WhiteElo "1932"]
[BlackElo "2252"]

1. d4 Nf6 2. Nf3 e6 3. e3 b6 4. Bd3 Bb7 5. Nbd2 c5 6. c3 Nc6 7. O-O d5 8. dxc5 Bxc5 9. e4 O-O 10. Qe2 dxe4 11. Nxe4 Be7 12. Bg5 Nxe4 13. Qxe4 g6 14. Bh6 Re8 15. Rad1 Qc7 16. Bf4 Bd6 17. Bxd6 Qxd6 18. Qh4 Qe7 19. Ng5 h5 20. Rfe1 Kg7 21. Re3 Rad8 22. Qg3 Qd6 23. f4 Ne7? {+/- 3.26} 24. Rde1? {(=, -0.05) gives away the advantage} (24. Nxf7! {was correct} Kxf7 25. Bxg6+ Nxg6 26. Rxd6 Rxd6 27. f5 e5!? 28. fxg6+ Rxg6 29. Qf2+ Kg7 30. g3 Rf6 {+/- 3.38}) 24... Nd5?? {(-/+, -9.72) An unfortunate choice. In fact, a howler. Almost any other black move is better, including} (24... Bc6) (24... Rf8) (24... Bd5 {, or}) (24... Qc6) 25. Nxf7! {destruction with tempo} Kxf7? {Now it's mate in 5.} (25... Qxf4!? {(+/-, 11.67)} 26. Qxg6+ Kf8 27. Rf3 {is also winning}) 26. Qxg6+ Kf8 27. Qh6+ Kf7 28. Bg6+ Kf6 29. Bxe8+ (29. Bxh5+ {is faster, but the text works fine.} ) 1-0
</code></pre>

<p>For an example of how this question of "when to resign" plays out (no pun intended) at the GM level, see my response to the question <a href="https://chess.stackexchange.com/questions/59/is-it-possible-to-force-checkmate-with-king-knight-and-bishop-vs-king/15477#15477">"Is it possible to force checkmate with King, knight, and Bishop vs. King?</a> (It is, of course, but apparently some GM's still want their opponents to prove it...).</p>
 8860: <p>"No game was ever won by resigning." -Tartakover</p>

<p>If playing on the team of opponents in a timed simultaneous exhibit,
resigning makes it easier on the exhibitor and thus harder on your teammates.
Thus one is often advised to <em>never</em> resign in this setting: even if your position
is hopeless, you may still help your teammates by forcing the exhibitor to actually win it.  Then again, some may regard this advice as unsportsmanlike.</p>
 4418: <p>I take 3 things into consideration when thinking about resigning:</p>

<p>1) The position on the clocks</p>

<p>2) The position on the board</p>

<p>3) The relative strength of my opponent</p>

<p>First off, if either I or my opponent are down to the last 2 minutes on the clock then I usually play on unless I'm really staring down the barrel. Something might happen and if it is disrespectful or masochistic it is only for another couple of minutes.</p>

<p>A concrete example of this the other way round happened to me a couple of years ago. I was winning comfortably (much better position plus an exchange and 2 pawns up) against a player rated about 200 points stronger than me. But, and it's a big but, I had 5 minutes left and he had 50 minutes. He played on, naturally, and with his extra time and the pressure I felt to try and win he managed to win.</p>

<p>Another player I know who has been within 50 ratings points of me for most of the last 15 years always used to resign the move before checkmate regardless of the situation or opponent. I found this deeply disrespectful and on one occasion about 12 years ago tried to teach him a lesson. I got a comfortable material advantage to the extent that I could do pretty much what I wanted. I still had 5 pawns left at this stage and implemented the following plan. </p>

<p>I won all his remaining pawns and then started advancing my 5 connected pawns up the board as a unit. Once I had 5 pawns on the 7th rank I started queening them with the intention of ending up with 5 queens on the board if possible. He resigned after I queened the third pawn and explained to me that he was resigning because I had a mate in 3. I counter explained that I wasn't interested in mate until I'd queened all 5 pawns (in case he hadn't guessed).</p>

<p>He appeared at the time to be completely unaffected by this although maybe other, more blunt, folk had a word with him because the last time I beat him he resigned in an endgame a pawn down when I was 2 or 3 moves from queening a pawn.</p>

<p>I've never lost to a player more than 200 points lower than me (due as much as anything to lack of opportunity) but when I beat a master rated about 500 points higher than me he resigned 3 or 4 moves before an inevitable checkmate. Fair enough, I think.</p>

<p>At the other extreme about 10 years ago playing a player about 200 points stronger than me I was completely outplayed in the opening and middlegame and as his threats mounted I found myself losing the exchange. </p>

<p>To his surprise I resigned. Why didn't I play on, he wanted to know, I was only an exchange down. The problem, I explained to him, was that before I lost the exchange I had a desperate position and after I lost the exchange I still had a desperate position only now I was an exchange down and within a few moves more material was going to follow and I would still be in a desperate position. He seemed disappointed, the sadist!</p>

<p>On the other hand I have several times against stronger opposition had the experience during the postmortem after a loss finding out that my opponent and I both had the impression that we were winning until quite late in the game, mistakenly on my part, obviously. They may very well have felt that I could have resigned sooner. Unfortunately my ability to evaluate the position accurately wasn't good enough to know that I was losing and should have resigned! If it had been I wouldn't have got into that position in the first place.</p>
 17: <p>The right time to resign is when you are have a disadvantage that is so large that you will reasonably expect to lose. This depends on your strength, and that of your opponent.</p>

<p>Between masters or higher, if one is behind by a clear pawn or more without positional or other compensation, it might be time to resign. On the other hand, as between beginners, even a piece behind might not call for a resignation, because the other beginner might easily lose it back.</p>
 35: <p>I was able to draw or even win some games I considered "clearly lost", especially if the opponent needed to know some theory (knight and bishop ending, Lucena and Philidor positions, opposition rules...). Consider the possibility of stalemate, or draw by repetition, too. This is often unexpected for the opponent, especially as you may launch a kamikaze attack and sacrifice lots of material in these cases.</p>
 167: <p>The right time to resign will vary from player to player, even if facing identical losing positions. But basically, the right time to resign is when, despite serious contemplation and effort of thought, you are convinced that there is simply no way to avoid a loss, and in addition you have lost all desire to play the position out. That said, there is nothing more frustrating than <a href="http://timkr.home.xs4all.nl/chess2/resigntxt.htm">resigning prematurely</a>, and a saying I've heard before goes something like "It's better to resign one move too late than one move too early," or "It's never too late to resign."</p>

<p>Some players can feel disrespected if an opponent plays on in what the first player considers a clearly lost position. But of course what one person can see clearly, others sometimes can't (or, not unlike the link above, the player who thinks it is already won might be mistaken). A player has every right to play until the bitter end every game without resigning -- <em>these times can even be great learning experiences</em>, seeing how one's opponent goes about winning a won position -- and I believe it is never disrespectful to do so, provided that the player on the losing end isn't, say, just running out the clock, motivated only by a desire to be annoying and waste the opponent's time.</p>
