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Connecting to SQL Server from SSMA (the certificate chain was issued by an authority that is not trusted!)

I am trying to use SQL Server Migration Assistant for the first time from my home PC. I have SQL Server in one Docker container and Oracle in another. I can connect to Oracle from SSMA, however when trying to connect to SQL Server I see this error:

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I have read plenty of questions on here that explain how to resolve the problem if it is seen when connecting from SQL Studio Manager e.g. this one: The certificate chain was issued by an authority that is not trusted. I have no problem connecting from SQL Studio Manager – just SSMA. How can I connect to SQL server from SSMA?

I have tried unticking ‘Encrypt connection’ on the SSMA SQL Server login window and I see the same error.

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Redirecting domains on https without creating a certificate for them?

I own, say, 100 domains. I want to add redirect for each of them to a new domain. And not only to a domain, but a custom query string. For instance

domain1.example/url1 -> domain11.example/url2 domain2.example/url1/url4 -> domain15.example/fdsafds/url33/url555  # and so on......., 100 domains with 100+ URLs each 

All the original URLs and the new ones are known beforehand. And there’re hundreds of URLs for each domain.

Requirement: there has to be an intermediate "domain-redirector" via which the domains will be redirected, and that’ll do all the job:

domain1.example/url1 -> my_redirector.example/url1 -> domain11.example/url2 domain2.example/url1/url4 -> my_redirector.example/url1/url4 -> domain15.example/fdsafds/url33/url555  # and so on....... 

This way I’d create A record for each of the domains pointing to my_redirector.example. And at my_redirector.example I’d be able to extract a) original query string from the URL b) original domain

Note that it needs to work with both http and https.

Question 1: will original domain and URL or query path be accessible at my_redirector.example?

Question 2: will I have to create a SSL certificate for each of the original domains domain1-domain100 at my_redirector.example, in order to be able to redirect https requests?

P.S. I’m a developer, therefore I’m capable of writting a custom utility to facilitate redirects at my_redirector.example

Certificate Signed Using Weak Hashing Algorithm impact on a workstation

I did a vulnerability scan on some of our company workstations. These are workstations used by employees (dev, HR, accounting, etc.) to do their job. One of the common result I found is SSL/TLS Certificate Signed Using Weak Hashing Algorithm. Based on the vulnerability description "An attacker can exploit this to generate another certificate with the same digital signature, allowing an attacker to masquerade as the affected service." I’m thinking this is more on a server side.

My question is, what could be the impact of this in an ordinary workstation?
What can an attacker/pentester do to the workstation with this vulnerability?

JWK with X.509 Certificate – is self signed okay?

I’m working with a client that, in order to use their OAuth 2.0 web API, requires me to provide them with a JWK that contains an embedded X.509 certificate. Then, when I’m requesting information from the API, they say I need to pass a "signed (with private keys) JWT Bearer token" on each request.

I’ve never worked with JWK’s before so I was looking over the official JWK documentation, but it’s very dense and doesn’t really talk about how these are used in real life applications.

I found this site / command line tool that can generate JWK’s in different formats, and it generates the JWK with an X.509 certificate that is self-signed. I’m wondering, in this case, is it okay to use a self-signed cert to talk to this API? I understand that with web browsers, you absolutely need a cert that is from a trusted CA because the client and web server are essentially strangers, but this cert isn’t being used publicly for a website; it’s just being used between my application and this OAuth API, and both parties already trust each other.

So really my question is, would generating a JWK with a self-signed X.509 certificate be sufficient, and then use the private key of the certificate to sign JWT Bearer tokens when actually using the API?

Does sslstrip have to do something with Bettercap’s certificate?

I am trying to perform a MITM attack using bettercap against a website that doesn’t have the HSTS security policy implemented at all.

When I try the following command: bettercap -T AddressIpoftheTarget -X --proxy --https-proxy, it works fine. Bettercap succeeds in injecting his own self-signed certificate to the web browser. The browser shows the "Not Secure" warning, and lets me accept the invalid certificate by proceeding to the website in an unsecure way.

When I try this command: bettercap -T AddressIpoftheTarget -X --https-proxy it doesn’t work. I don’t understand why the --proxy is needed. Is it because it enables the sslstrip? How does sslstrip contribute in all of this during this scenario?

What are the security implications of adding an Intermediate Certificate into the Trusted Root Store in Windows?

I have 2 certificates (one root and one intermediate).

In Windows OS, the Root certificate is in the trusted root store (for current user). The other intermediate certificate (signed by the root CA), is to be found (under current user also) under the Intermediate CA store.

I am using SSL verification in one of my client applications (Kafka Confluent) and realized the client only enumerates certificates in the root store. Therefore SSL handshake fails (the intermediate CA is needed).

One solution is to import that certificate into the Trusted Root Certificate Authorities. With that solution, SSL verification at client works. However, is there any concern in doing so?

From security point of view does it make a difference if the intermediate CA exists in the Root store vs the Intermediate store on Windows?

UPDATE If more context is needed as to what exactly I am facing you can check the issue here https://github.com/edenhill/librdkafka/issues/3025

Why would a certificate authority have multiple root certificates?

When I look at the trusted certificates in my browser, I see that many certificate authorities have multiple root certificates associated with them. For example, org-Amazon has Amazon Root CA 1, Amazon Root CA 2, Amazon Root CA 3, and Amazon Root CA 4.

How do the purposes of these four certificates differ?

I also see that some CAs have root certificates of different "tiers", such as gold, silver, and platinum. What’s the deal with these? I imagine there are price differences associated with the different tiers, but what extra service could they be offering?