>> What we definitely should do here is at least frame this check with
>>> That being said, what ends up in the high bits of esp when we iret to
>>> vm86 mode?
>>
>> I don't know. I guess it's time to write an actual vm86 testcase :)
>
> Ick.  I can try...

I found an example which runs small bit of 16-bit code using vm86 machinery.
Tried in 32-bit kernel under qemu, it worked: printed "Hello".
/*
 * Adaped from: runcom version 0.1 (c) 2003 Fabrice Bellar
 * "Simple example of use of vm86: launch a basic .com DOS executable"
 *
 * gcc -m32 -Os -Wall -static vm86.c -ovm86
 */
#include <stdlib.h>
#include <stdio.h>
#include <string.h>
#include <inttypes.h>
#include <unistd.h>
#include <fcntl.h>
#include <sys/mman.h>
#include <signal.h>
#include <linux/unistd.h>
#include <asm/vm86.h>
#include <sys/vm86.h>

//#define SIGTEST

#define COM_BASE_ADDR    0x10100

static inline void set_bit(uint8_t *a, unsigned int bit)
{
    a[bit / 8] |= (1 << (bit % 8));
}

static inline uint8_t *seg_to_linear(unsigned int seg, unsigned int reg)
{
    return (uint8_t *)((seg << 4) + (reg & 0xffff));
}

static inline void pushw(struct vm86_regs *r, int val)
{
    r->esp = (r->esp & ~0xffff) | ((r->esp - 2) & 0xffff);
    *(uint16_t *)seg_to_linear(r->ss, r->esp) = val;
}

void dump_regs(struct vm86_regs *r)
{
    fprintf(stderr,
            "AX=%08lx BX=%08lx CX=%08lx DX=%08lx\n"
            "SI=%08lx DI=%08lx BP=%08lx SP=%08lx\n"
            "IP=%08lx FL=%08lx\n"
            "CS=%04x DS=%04x ES=%04x SS=%04x FS=%04x GS=%04x\n",
            r->eax, r->ebx, r->ecx, r->edx, r->esi, r->edi, r->ebp, r->esp,
            r->eip, r->eflags,
            r->cs, r->ds, r->es, r->ss, r->fs, r->gs);
}

#ifdef SIGTEST
void alarm_handler(int sig)
{
    fprintf(stderr, "alarm signal=%d\n", sig);
    alarm(1);
}
#endif

extern char code16;
extern char code16_end;

int main(int argc, char **argv)
{
    uint8_t *vm86_mem;
    int ret, seg;
    struct vm86plus_struct ctx;
    struct vm86_regs *r;

    vm86_mem = mmap((void *)0x00000000, 0x110000,
                    PROT_WRITE | PROT_READ | PROT_EXEC,
                    MAP_FIXED | MAP_ANON | MAP_PRIVATE, -1, 0);
    if (vm86_mem == MAP_FAILED) {
        perror("mmap");
        exit(1);
    }
#ifdef SIGTEST
    {
        struct sigaction act;

        act.sa_handler = alarm_handler;
        sigemptyset(&act.sa_mask);
        act.sa_flags = 0;
        sigaction(SIGALRM, &act, NULL);
        alarm(1);
    }
#endif

    /* load 16-bit code at COM_BASE_ADDR */
    memcpy(vm86_mem + COM_BASE_ADDR, &code16, &code16_end - &code16);

    memset(&ctx, 0, sizeof(ctx));
    /* init basic registers */
    r = &ctx.regs;
    r->eip = 0x100;
    r->esp = 0xfffe;
    seg = (COM_BASE_ADDR - 0x100) >> 4;
    r->cs = seg;
    r->ss = seg;
    r->ds = seg;
    r->es = seg;
    r->fs = seg;
    r->gs = seg;
    r->eflags = 1 << 19; //EFLAGS.VIF

    set_bit((uint8_t *)&ctx.int_revectored, 0x21);
    /* put return code */
    *seg_to_linear(r->cs, 0) = 0xb4; /* mov ah, $0 */
    *seg_to_linear(r->cs, 1) = 0x00;
    *seg_to_linear(r->cs, 2) = 0xcd; /* int $0x21 */
    *seg_to_linear(r->cs, 3) = 0x21;
    pushw(&ctx.regs, 0x0000);

    for(;;) {
        ret = vm86(VM86_ENTER, &ctx);
        switch(VM86_TYPE(ret)) {
        case VM86_INTx:
            {
                int int_num, ah;

                int_num = VM86_ARG(ret);
                if (int_num != 0x21)
                    goto unknown_int;
                ah = (r->eax >> 8) & 0xff;
                switch(ah) {
                case 0x00: /* exit */
                    exit(0);
                case 0x02: /* write char */
                    {
                        uint8_t c = r->edx;
                        write(1, &c, 1);
                    }
                    break;
                case 0x09: /* write string */
                    {
			int ptr = r->edx;
                        uint8_t c;
                        for(;;) {
                            c = *seg_to_linear(r->ds, ptr++);
                            if (c == '$')
                                break;
                            write(1, &c, 1);
                        }
                        r->eax = (r->eax & ~0xff) | '$';
                    }
                    break;
                default:
unknown_int:
                    fprintf(stderr, "unsupported int 0x%02x\n", int_num);
                    dump_regs(&ctx.regs);
                    //                    exit(1);
                }
            }
            break;
        case VM86_SIGNAL:
            /* a signal came, we just ignore that */
            break;
        case VM86_STI:
            break;
        default:
            fprintf(stderr, "unhandled vm86 return code (0x%x)\n", ret);
            dump_regs(&ctx.regs);
            exit(1);
        }
    }
}

void code()
{
	asm volatile("\n"
	"	.code16""\n"

	"code16:""\n"
	"	mov	$(0x100+msg-code16),%dx""\n"
	"	mov	$0x09,%ah""\n"
	"	int	$0x21""\n"
	"	ret""\n"

	"msg:""\n"
	"	.string	\"Hello\"""\n"
	"	.byte	10""\n"
	"	.string	\"$\"""\n"

	"code16_end:""\n"
	"	.code32""\n"
	);
}

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