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In Iron Man 1, around 1:30:00, Tony sends Pepper into his office to download some files off his work computer.

  1. Why couldn't he do that himself?
  2. Why couldn't he connect to it remotely over some kind of corporate VPN? I'd think Stark would be all about telework.
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    It needn't have been a VPN - it could have been over an "actual" private network, or possibly even a secure protocol over an insecure network. – mwfearnley Dec 28 '19 at 15:13
51
  1. Tony did not want to tip his hand to Obadiah Stane that he was suspicious of him. Obadiah had been cordial up to that point (and given that Obadiah tries to kill him afterward, Tony's fears would have been well founded). Since Tony was not a frequent visitor to the building where Obadiah's office was located, and Pepper was, it made more sense for her to go.
  2. VPNs were uncommon in 2008 and probably not that well known by Hollywood writers or the general movie-going audience. Also, the Internet has changed a lot since 2008. To put this into perspective, consider this line from the movie

    I don't wanna see this on your MySpace page.

    MySpace was still a larger social network than Facebook at the time

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    The problem with a corporate VPN is that, well, it's administered by the corporation. Stane runs the corporation. It would be easy for him to tap any suspicious access like that. – Cadence Dec 27 '19 at 2:25
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    Re: the web being very different in 2008. Yeah, in 2008, the first mobile web pages were made. Think of that. The first iPhone was in its first year, and before it, no one had web page designs for screens smaller than a 800x600 monitor. – Joseph Hansen Dec 27 '19 at 5:06
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    @JosephHansen Of course, they had them before. There were sites built with XHTML Mobile, before that there were sites based on WML. iPhone just speed up what had already been developing for quite some time for feature phones, smartphones, and PDAs. – Malcolm Dec 27 '19 at 12:26
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    "VPNs were uncommon in 2008" ???? Not sure what the relevance is either of mobile webpages or the reigning social media entity of the era. If nothing else, remote computing has been a staple of this kind of fiction, including the comic source material, for decades and decades and decades. I find it preprosterous (:P) to presume that audiences wouldn't understand it, and therefore unlikely that this was the reason that producers shied away from it in the film. Point 1 is good - it's because this is drama – Lightness Races with Monica Dec 27 '19 at 16:21
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    @LightnessRaceswithMonica I think it's a case of Reality Is Unrealistic. There's a conscious effort in Iron Man (and most early 2000s superhero movies) to make the story feel grounded and like something that could happen in the real world. If audiences weren't familiar with real-world remote computing technologies at the time, they would assume it's a fictional technology, and that would hurt what the filmmakers were trying to achieve. – Justin Dec 27 '19 at 21:27
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Machavity’s point #1 is a good explanation, but I don’t think point #2 is on the money. Although VPNs might not have been as common in 2008, remote access was definitely well established. I was personally using ssh as far back as 1999 for remote access to my employer’s computers, and an ISDN connection as far back as 1995—and I’m no billionaire. Tony Stark would for sure have had remote access to Stark Industries’ internal network.

However, the files to be copied were very large. Transferring them over Tony’s remote connection would probably cause a large and sustained increase in the connection’s bandwidth metrics. Stark Industries’ IT security staff would have a network dashboard with a graph that would make the increase obvious, and the increase might trip alarms.

2

In addition to the accepted answer:

After Tony announced that Stark Industries was exiting weapons production he was ousted as CEO by his own Board of Directors, who secured an injunction to lock him out. Tony owned a controlling interest in the company, and eventually would have been able to prevail in a dispute with the board, but at that moment he was effectively in exile. Pepper, however, remained a Stark Industries employee.

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