DiagnOSe MacOS Internet

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Understanding Internet Addressing When using the Internet, you may have a Public IPv4 address such as 153.64.225.225 or an IPv6 address like 2000:37e9:6e5b:6098:6400:9c10:fd45:ac7e. These can be verified from https://test-ipv6.com/. However, for those who are not familiar with technical aspects, communicating these addresses, or even mentioning MAC addresses like 5e:22:83:bc:93:04, can be prone to errors and quickly become complex. –
Understanding Internet Addressing When using the Internet, you may have a Public IPv4 address such as 153.64.225.225 or an IPv6 address like 2000:37e9:6e5b:6098:6400:9c10:fd45:ac7e. These can be verified from https://test-ipv6.com/. However, for those who are not familiar with technical aspects, communicating these addresses, or even mentioning MAC addresses like 5e:22:83:bc:93:04, can be prone to errors and quickly become complex.

Understanding Internet Addressing

When using the Internet, you may have a Public IPv4 address such as 153.64.225.225 or an IPv6 address like 2000:37e9:6e5b:6098:6400:9c10:fd45:ac7e. These can be verified from https://test-ipv6.com/. However, for those who are not familiar with technical aspects, communicating these addresses, or even mentioning MAC addresses like 5e:22:83:bc:93:04, can be prone to errors and quickly become complex. Moreover, this does not provide any historical data, especially when past issues occurred.

When accessing a webpage like https://bashirian.org, you first reach a DNS server to translate the host portion (bashirian) along with the Top Level Domain (org) of the URL to an IP address like 188.17.244.84. Your computer and browser actually sends its type with all web requests, for example:
Opera/9.80 (X11; Linux i686; Ubuntu/14.10) Presto/2.12.388 Version/12.16.

The Significance of Default Gateways

Your default gateway is usually an automatically configured address via DHCP. You receive a default gateway like 172.28.31.200 (although they typically end in .1 or .254 based on the scope size), and this is where your computer sends all its traffic to be routed onwards. For IPv6, a detailed explanation can be found at how-to-fix-ipv6-connectivity/, but you can verify on Mac or Linux with:

IPv4 Routes and the Host IPv4 Route Table (inc. VPN)

netstat -rn -f inet | egrep -i "default|0/1|128.0/1"

0/1      172.18.12.193  UGScg  utun3
default  172.28.31.200    UGScg  en0
128.0/1  172.18.12.193  UGSc   utun3

Note: We are not just looking for the default but also for any VPN that overrides the public v4 address space.

IPv6 Routes and the Host IPv6 Route Table (inc. VPN)

netstat -rn -f inet6 | egrep -i "default|2000::/3"

If you have IPv6 active the above should return at least one route (as per below) via a known interface such as “en0 " on a Mac.

default   fe80:ee07:e991:26f6:b3a5%en0  UGcg   en0
default   fe80::%utun0                   UGcIg  utun0
default   fe80::%utun1                   UGcIg  utun1
default   fe80::%utun2                   UGcIg  utun2
2000::/3  utun3                          USc    utun3

Note: We are not just looking for the default but also for any VPN that overrides the public v6 address space.

Debugging DHCP for both IPv4 and IPv6

To get a look at the low level DHCP configuration (Mac/Linux):

ipconfig getpacket en0

...
domain_name_server (ip_mult): {49.87.74.144, 209.132.112.27}
end (none):
...

So, in the above we are not getting IPv6 DNS servers from the DHCPv4 reply but…

ipconfig getv6packet en0

DHCPv6 REPLY (7) Transaction ID 0x80940b Length 76
Options[4] = {
  CLIENTID (1) Length 14: DUID LLT HW 1 Time 668691856 Addr 5e:22:83:bc:93:04
  DNS_SERVERS (23) Length 32: 2606:4700:4700::1111, 2001:4860:4860::8844
  DOMAIN_LIST (24) Length 0:  Invalid
  SERVERID (2) Length 10: DUID LL HW 1 Addr b2:7a:6a:29:e0:06
}

Fixing Connectivity Issues for Wired and Wireless Networks

In the realm of networking, the use of either a wired or wireless (Wi-Fi) medium at the physical and data layer is common when transmitting data to your router.

Resolving Problems on Apple macOS / OSX

Regardless of whether your system is running on OSX/macOS versions like 10.12.2, 11.0.4, or 12.1.7, there are a variety of troubleshooting tools available. However, these manual actions and scripts do not provide a series of interconnected values over time. This is where automated remote troubleshooting proves to be beneficial, especially for teams that adopt remote work and Work From Anywhere (WFA) culture.

Utilizing Built-in Scripts and Commands for Assistance

An extremely valuable diagnostic tool on OSX/macOS is sudo wdutil info, which imparts a dump of the current wireless settings to the CLI. This tool can also be configured to generate specific logs for troubleshooting. Additionally, the sysdiagnose tool offers a more comprehensive approach, generating a wide range of logs (though much of it is only relevant to wireless at a specific point in time, similar to wdutil).

Running sudo nohup /usr/bin/sysdiagnose -u & in the background will create logs in /var/tmp/<blah>.tar.gz. For an interactive (albeit limited) experience, you can execute
sudo /usr/bin/sysdiagnose, which will prompt a privacy warning. When not run in the background, it should open Finder in the designated location or you can manually navigate to /var/tmp or use Finder with Cmd+Shift+G to pinpoint the path. Be cautious of the file sizes, which can amount to around 300MB.

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