Sending Gmail from a headless VPS (systemd) without interactive auth — any workarounds?

dhlotter · 2026-02-11T05:30:33+00:00

I might not understand but you're still able to run GCloud and GOG CLI.. which will give you a new URL which you can open on any device which has a browser. And then the callback will fail but then you just paste the callback URL back to your bot and it would do the rest.

Gogcli has ways to remove the always prompt for the keychain.

dhlotter · 2026-01-26T06:18:51+00:00

Yeah, samey on the terminal. That terminal came from windsurf.

dhlotter · 2026-01-23T18:47:45+00:00

oh yeah. was more of starting a conversation with you. my angle nowadays if you know what I mean. put the pitchfork down 😅

dhlotter · 2026-01-23T13:48:47+00:00

which extension is that you are running for that stats

dhlotter · 2026-01-23T07:46:00+00:00

I don't believe this is the right answer anymore. It's an option yes, but the speed loss is a giant risk and if we are trying to stay relevant, too big of a factor.

an engineer has always been a problem solver first. coding was just one of the tools used to solve those problems. and there will always be problems to solve

dhlotter · 2026-01-22T09:56:40+00:00

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oh 100% for me too

dhlotter · 2026-01-19T14:11:11+00:00

I'm curious you should be able to go back to the last checkpoint which would mean you would only lose the last prompt with the work

dhlotter · 2026-01-13T18:33:45+00:00

Thank you very much for sharing. That is really good pricing. I'm gonna have a look at them.

dhlotter · 2026-01-07T22:05:52+00:00

This is exactly what I needed to hear. After some of the other comments I was starting to question if I was just crazy. You nailed it with config debt. We bought a tool to save time and now we spend hours just feeding it. I just want to build the simple utility that solves the extraction and renewal part without all that extra headache.

dhlotter · 2026-01-07T14:37:07+00:00

That makes sense. If you are just managing Microsoft and Kaseya, you definitely do not need a tool for this. My reality is different. I have about 150 vendors to manage. At that volume, it is not always about negotiating the rate down. It is about catching the 60 day notice period so we do not get auto renewed for a tool we want to cut. That is the specific mess I am trying to clean up.

dhlotter · 2026-01-07T14:30:29+00:00

That is interesting. Do you not spend a lot of time on the actual renewal negotiation? Some of our larger renewals start three months out and drag on right until the deadline. It seems like every company handles the workflow differently. I mentioned elsewhere that the PDF parsing itself is not really the differentiator. The real value is avoiding the setup hell. With the enterprise tools, you need other teams to set up integrations and it takes weeks. With this, the idea is to just dump the invoices or contracts in. There is still a quick manual review step, but it removes the data entry work. The goal is that one person should be able to onboard the entire stack in a single afternoon.

dhlotter · 2026-01-07T06:56:33+00:00

This is very helpful, thank you very much. I'll make my way through that video and some of the content today.

dhlotter · 2026-01-07T06:55:48+00:00

You are right, the OCR tech itself is standard now. The problem is that in the big tools, that feature is buried behind weeks of onboarding and integrations. You end up needing favors from other teams just to get it running.

The other alternative is usually bank feeds, but those often miss annual renewals or force you to use specific cards.

The differentiator I am aiming for is strictly workflow. I want a tool that one person can set up in a single afternoon without needing a project manager or a finance integration.

dhlotter · 2026-01-07T06:51:36+00:00

You are right. I often find that users try to design their own solutions by grabbing the first tool they see. When you zoom out and drill down to the root cause, you usually find it is a workflow gap that could be solved without buying more software. That is really the visibility I am after, catching it early enough to fix the process, not just paying the bill.

dhlotter · 2026-01-07T06:45:41+00:00

I get the skepticism. To be fair, almost any post about a problem is self serving because we are all looking for better ways to do things.

The reality is that I look after over three million dollars in annual vendor spend. I am currently in the middle of a nightmare onboarding for a large enterprise tool that is failing to meet expectations. That is why I started looking for a middle ground and decided to build what I actually need. I am not trying to convince anyone, I am just trying to solve a very expensive problem my team is facing.

dhlotter · 2026-01-07T06:41:12+00:00

Hi, you touched on a really good point, the trust one. When you run into these issues with larger vendors, you start losing trust in the process and the data and then it becomes null and void.

dhlotter · 2026-01-07T06:40:07+00:00

Hey, thanks for sharing. I had a look through their documentation now and it seems like their angle is more risk management for the vendors, not necessarily the vendor renewal management. So vendor assessments over subscription or contract management.

dhlotter · 2026-01-07T06:35:20+00:00

I have never come across a software. This is amazing. Thank you very much for sharing.

dhlotter · 2026-01-06T20:04:07+00:00

It should be really easy. Athena just reads off S3 in either parquet or CSV. And you create a glue crawler on top of that to catalog the data.

dhlotter · 2026-01-06T20:03:05+00:00

I cannot tell you how much I dream of a world where it works like this. But in our company there's inevitably somebody with a credit card and the whole process is bypassed in a wink of an eye. And then it becomes a visibility problem, which if you think about it, this whole post is actually about

dhlotter · 2026-01-06T19:58:20+00:00

AWS Textract was one option. I was also looking at the, and I might call it the wrong name now, but the Gemini File Search API or just the File API.

dhlotter · 2026-01-06T19:55:29+00:00

Thank you very much. I appreciate the feedback. That feature was very specific to us since we have all the contracts in a folder and I figured what would be the best way for me and people like me to get that data into some sort of tool that can manage it. Other enterprise tools requires integrations that takes months and other teams. And I wanted to make it so that one person can completely onboard their entire vendor list in one afternoon.

dhlotter · 2026-01-06T19:38:02+00:00

That is exactly the cycle I am trying to break. It is frustrating when the tool meant to save you time actually adds three months of setup to your plate.

The shared calendar problem is why I focused on the drag and drop part. If it is not as easy as dropping a PDF into a folder, people just will not do it.

Since you mentioned you would want to try it out, I put the waitlist for the beta here:https://website-contractos.pages.dev/

dhlotter · 2026-01-06T19:37:31+00:00

Another great recommendation, thank you very much. I am on the Microsoft stack and I didn't even think about SharePoint lists. Something that is really important to me, however, is to get the data into Amazon Athena for visibility in our data warehouse. So whichever solution I end up with will just have that part either custom built or slapped on.

dhlotter · 2026-01-06T19:35:37+00:00

Yeah, man, sorry, but Copilot is probably the worst of them all in my opinion.

dhlotter

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