Cannot install packages with pip - timeout error

### My Platform

OS is WSL: Ubuntu-22.04
(installed on W10)

Pip version: 22.3.1 (on Python 10)
CURL version: 7.81.0 (x86_64-pc-linux-gnu)

- Doesn´t work on Ubuntu-20.04 too
- Connecting to pypi.org via browser is possible,
- Pip probably timeouts on TLS handshake (see the curl command)
- HTTPS CURL from WSL to other websites sometimes work, sometimes doesn´t. For ex. ```curl https://windows.com``` does not work, ```curl https://seznam.cz``` works. ((edited after issue submission))
- HTTPS CURL from Windows CMD to pypi.org works fine
- also works on an Ubuntu WM on the same PC
- adding ```--default-timeout=100``` to the pip command doesn´t help
- adding ```--trusted-host pypi.org --trusted-host pypi.python.org --trusted-host files.pythonhosted.org``` doesn´t help
- turning off firewall and Windows Defender doesn´t help
- changing network doesn´t help
- reinstalling WSL and trying pip from fresh installation doesn´t help






### Fastly Debug

``` (paste your output on the next line)
$ sudo python3 -m pip install -Uvvv pip
Using pip 22.3.1 from /usr/local/lib/python3.10/dist-packages/pip-22.3.1-py3.10.egg/pip (python 3.10)
Non-user install because site-packages writeable
Created temporary directory: /tmp/pip-build-tracker-j40a1mry
Initialized build tracking at /tmp/pip-build-tracker-j40a1mry
Created build tracker: /tmp/pip-build-tracker-j40a1mry
Entered build tracker: /tmp/pip-build-tracker-j40a1mry
Created temporary directory: /tmp/pip-install-7ztvrwuh
Created temporary directory: /tmp/pip-ephem-wheel-cache-77sav5ko
Requirement already satisfied: pip in /usr/local/lib/python3.10/dist-packages/pip-22.3.1-py3.10.egg (22.3.1)
1 location(s) to search for versions of pip:
* https://pypi.org/simple/pip/
Fetching project page and analyzing links: https://pypi.org/simple/pip/
Getting page https://pypi.org/simple/pip/
Found index url https://pypi.org/simple
Looking up "https://pypi.org/simple/pip/" in the cache
Request header has "max_age" as 0, cache bypassed
Starting new HTTPS connection (1): pypi.org:443
Incremented Retry for (url='/simple/pip/'): Retry(total=4, connect=None, read=None, redirect=None, status=None)
WARNING: Retrying (Retry(total=4, connect=None, read=None, redirect=None, status=None)) after connection broken by 'ReadTimeoutError("HTTPSConnectionPool(host='pypi.org', port=443): Read timed out. (read timeout=15)")': /simple/pip/
Starting new HTTPS connection (2): pypi.org:443
Incremented Retry for (url='/simple/pip/'): Retry(total=3, connect=None, read=None, redirect=None, status=None)
WARNING: Retrying (Retry(total=3, connect=None, read=None, redirect=None, status=None)) after connection broken by 'ReadTimeoutError("HTTPSConnectionPool(host='pypi.org', port=443): Read timed out. (read timeout=15)")': /simple/pip/
Starting new HTTPS connection (3): pypi.org:443
Incremented Retry for (url='/simple/pip/'): Retry(total=2, connect=None, read=None, redirect=None, status=None)
WARNING: Retrying (Retry(total=2, connect=None, read=None, redirect=None, status=None)) after connection broken by 'ReadTimeoutError("HTTPSConnectionPool(host='pypi.org', port=443): Read timed out. (read timeout=15)")': /simple/pip/
Starting new HTTPS connection (4): pypi.org:443
Incremented Retry for (url='/simple/pip/'): Retry(total=1, connect=None, read=None, redirect=None, status=None)
WARNING: Retrying (Retry(total=1, connect=None, read=None, redirect=None, status=None)) after connection broken by 'ReadTimeoutError("HTTPSConnectionPool(host='pypi.org', port=443): Read timed out. (read timeout=15)")': /simple/pip/
Starting new HTTPS connection (5): pypi.org:443
Incremented Retry for (url='/simple/pip/'): Retry(total=0, connect=None, read=None, redirect=None, status=None)
WARNING: Retrying (Retry(total=0, connect=None, read=None, redirect=None, status=None)) after connection broken by 'ReadTimeoutError("HTTPSConnectionPool(host='pypi.org', port=443): Read timed out. (read timeout=15)")': /simple/pip/
Starting new HTTPS connection (6): pypi.org:443
Could not fetch URL https://pypi.org/simple/pip/: connection error: HTTPSConnectionPool(host='pypi.org', port=443): Max retries exceeded with url: /simple/pip/ (Caused by ReadTimeoutError("HTTPSConnectionPool(host='pypi.org', port=443): Read timed out. (read timeout=15)")) - skipping
Skipping link: not a file: https://pypi.org/simple/pip/
Given no hashes to check 0 links for project 'pip': discarding no candidates
Created temporary directory: /tmp/pip-unpack-qeoxwuvj
WARNING: Running pip as the 'root' user can result in broken permissions and conflicting behaviour with the system package manager. It is recommended to use a virtual environment instead: https://pip.pypa.io/warnings/venv
1 location(s) to search for versions of pip:
* https://pypi.org/simple/pip/
Fetching project page and analyzing links: https://pypi.org/simple/pip/
Getting page https://pypi.org/simple/pip/
Found index url https://pypi.org/simple
Looking up "https://pypi.org/simple/pip/" in the cache
Request header has "max_age" as 0, cache bypassed
Starting new HTTPS connection (1): pypi.org:443
Could not fetch URL https://pypi.org/simple/pip/: connection error: HTTPSConnectionPool(host='pypi.org', port=443): Max retries exceeded with url: /simple/pip/ (Caused by ReadTimeoutError("HTTPSConnectionPool(host='pypi.org', port=443): Read timed out. (read timeout=5)")) - skipping
Skipping link: not a file: https://pypi.org/simple/pip/
Given no hashes to check 0 links for project 'pip': discarding no candidates
WARNING: There was an error checking the latest version of pip.
See below for error
Traceback (most recent call last):
  File "/usr/local/lib/python3.10/dist-packages/pip-22.3.1-py3.10.egg/pip/_internal/self_outdated_check.py", line 227, in pip_self_version_check
    upgrade_prompt = _self_version_check_logic(
  File "/usr/local/lib/python3.10/dist-packages/pip-22.3.1-py3.10.egg/pip/_internal/self_outdated_check.py", line 196, in _self_version_check_logic
    remote_version = parse_version(remote_version_str)
  File "/usr/local/lib/python3.10/dist-packages/pip-22.3.1-py3.10.egg/pip/_vendor/packaging/version.py", line 49, in parse
    return Version(version)
  File "/usr/local/lib/python3.10/dist-packages/pip-22.3.1-py3.10.egg/pip/_vendor/packaging/version.py", line 264, in __init__
    match = self._regex.search(version)
TypeError: expected string or bytes-like object
Removed build tracker: '/tmp/pip-build-tracker-j40a1mry'
```


### DNS Resolution

```console (paste your output after the line with the dig command)
$ dig pypi.org A

; <<>> DiG 9.18.1-1ubuntu1.2-Ubuntu <<>> pypi.org A
;; global options: +cmd
;; Got answer:
;; ->>HEADER<<- opcode: QUERY, status: NOERROR, id: 31254
;; flags: qr rd ad; QUERY: 1, ANSWER: 4, AUTHORITY: 0, ADDITIONAL: 0
;; WARNING: recursion requested but not available

;; QUESTION SECTION:
;pypi.org.                      IN      A

;; ANSWER SECTION:
pypi.org.               0       IN      A       151.101.192.223
pypi.org.               0       IN      A       151.101.64.223
pypi.org.               0       IN      A       151.101.128.223
pypi.org.               0       IN      A       151.101.0.223

;; Query time: 0 msec
;; SERVER: 172.28.128.1#53(172.28.128.1) (UDP)
;; WHEN: Thu Nov 17 14:18:26 CET 2022
;; MSG SIZE  rcvd: 98

```

```console (paste your output after the line with the dig command)
$ dig pypi.org AAAA

; <<>> DiG 9.18.1-1ubuntu1.2-Ubuntu <<>> pypi.org AAAA
;; global options: +cmd
;; Got answer:
;; ->>HEADER<<- opcode: QUERY, status: NOERROR, id: 27382
;; flags: qr rd ad; QUERY: 1, ANSWER: 4, AUTHORITY: 0, ADDITIONAL: 0
;; WARNING: recursion requested but not available

;; QUESTION SECTION:
;pypi.org.                      IN      AAAA

;; ANSWER SECTION:
pypi.org.               0       IN      AAAA    2a04:4e42::223
pypi.org.               0       IN      AAAA    2a04:4e42:400::223
pypi.org.               0       IN      AAAA    2a04:4e42:200::223
pypi.org.               0       IN      AAAA    2a04:4e42:600::223

;; Query time: 0 msec
;; SERVER: 172.28.128.1#53(172.28.128.1) (UDP)
;; WHEN: Thu Nov 17 14:19:13 CET 2022
;; MSG SIZE  rcvd: 146

```

```console (paste your output after the line with the dig command)
$ dig files.pythonhosted.org A

; <<>> DiG 9.18.1-1ubuntu1.2-Ubuntu <<>> files.pythonhosted.org A
;; global options: +cmd
;; Got answer:
;; ->>HEADER<<- opcode: QUERY, status: NOERROR, id: 54578
;; flags: qr rd ad; QUERY: 1, ANSWER: 2, AUTHORITY: 0, ADDITIONAL: 0
;; WARNING: recursion requested but not available

;; QUESTION SECTION:
;files.pythonhosted.org.                IN      A

;; ANSWER SECTION:
files.pythonhosted.org. 0       IN      CNAME   dualstack.r.ssl.global.fastly.net.
dualstack.r.ssl.global.fastly.net. 0 IN A       146.75.117.63

;; Query time: 20 msec
;; SERVER: 172.28.128.1#53(172.28.128.1) (UDP)
;; WHEN: Thu Nov 17 14:19:27 CET 2022
;; MSG SIZE  rcvd: 158

```

```console (paste your output after the line with the dig command)
$ dig files.pythonhosted.org AAAA

; <<>> DiG 9.18.1-1ubuntu1.2-Ubuntu <<>> files.pythonhosted.org AAAA
;; global options: +cmd
;; Got answer:
;; ->>HEADER<<- opcode: QUERY, status: NOERROR, id: 46839
;; flags: qr rd ad; QUERY: 1, ANSWER: 2, AUTHORITY: 0, ADDITIONAL: 0
;; WARNING: recursion requested but not available

;; QUESTION SECTION:
;files.pythonhosted.org.                IN      AAAA

;; ANSWER SECTION:
files.pythonhosted.org. 0       IN      CNAME   dualstack.r.ssl.global.fastly.net.
dualstack.r.ssl.global.fastly.net. 0 IN AAAA    2a04:4e42:8d::319

;; Query time: 20 msec
;; SERVER: 172.28.128.1#53(172.28.128.1) (UDP)
;; WHEN: Thu Nov 17 14:19:43 CET 2022
;; MSG SIZE  rcvd: 170

```


### Traceroutes / IPv4

```console (paste your output after the line with the traceroute command)
$ traceroute pypi.org
traceroute to pypi.org (151.101.192.223), 30 hops max, 60 byte packets
 1  MSI.mshome.net (172.28.128.1)  0.471 ms  0.375 ms  0.367 ms
 2  o2smartbox2.home (10.0.1.138)  2.069 ms  2.438 ms  2.259 ms
 3  80.70.60.254 (80.70.60.254)  6.690 ms  8.468 ms  8.434 ms
 4  * * *
 5  90-183-197-114.rcq.o2.cz (90.183.197.114)  11.318 ms  11.480 ms  11.471 ms
 6  194.228.115.116 (194.228.115.116)  10.419 ms  11.515 ms  10.349 ms
 7  * * *
 8  90.182.80.193 (90.182.80.193)  13.224 ms  9.436 ms  9.576 ms
 9  194.228.115.35 (194.228.115.35)  10.111 ms  10.106 ms 194.228.115.33 (194.228.115.33)  10.922 ms
10  194.228.115.32 (194.228.115.32)  10.989 ms 194.228.115.34 (194.228.115.34)  11.931 ms 194.228.115.32 (194.228.115.32)  10.978 ms
11  prag-b4-link.ip.twelve99.net (62.115.58.198)  11.925 ms * *
12  * * ffm-bb2-link.ip.twelve99.net (62.115.124.28)  17.059 ms
13  * * *
14  * * *
15  * * *
16  * * *
17  * * *
18  * * *
19  * * *
20  * * *
21  * * *
22  * * *
23  * * *
24  * * *
25  * * *
26  * * *
27  * * *
28  * * *
29  * * *
30  * * *
```

```console (paste your output after the line with the traceroute command)
$ traceroute files.pythonhosted.org
traceroute to files.pythonhosted.org (146.75.117.63), 30 hops max, 60 byte packets
 1  MSI.mshome.net (172.28.128.1)  0.429 ms  0.394 ms  0.420 ms
 2  o2smartbox2.home (10.0.1.138)  2.071 ms  2.549 ms *
 3  * * 80.70.60.254 (80.70.60.254)  6.977 ms
 4  * * *
 5  90-183-197-114.rcq.o2.cz (90.183.197.114)  10.032 ms  9.929 ms *
 6  194.228.115.116 (194.228.115.116)  9.634 ms 194.228.115.115 (194.228.115.115)  8.716 ms  9.848 ms
 7  * * *
 8  90.182.80.225 (90.182.80.225)  9.139 ms  9.396 ms  8.911 ms
 9  194.228.115.35 (194.228.115.35)  10.200 ms 194.228.115.33 (194.228.115.33)  9.587 ms  9.958 ms
10  194.228.115.34 (194.228.115.34)  10.255 ms 194.228.115.32 (194.228.115.32)  9.750 ms 194.228.115.34 (194.228.115.34)  10.441 ms
11  prag-b4-link.ip.twelve99.net (62.115.58.198)  10.504 ms *  10.119 ms
12  * * *
13  * * *
14  * * *
15  * * *
16  * * *
17  * * *
18  * * *
19  * * *
20  * * *
21  * * *
22  * * *
23  * * *
24  * * *
25  * * *
26  * * *
27  * * *
28  * * *
29  * * *
30  * * *
```


### Traceroutes / IPv6 (If available)

```console (paste your output after the line with the traceroute command)
$ traceroute6 pypi.org
traceroute to pypi.org (2a04:4e42::223), 30 hops max, 80 byte packets
connect: Network is unreachable
```

```console (paste your output after the line with the traceroute command)
$ traceroute6 files.pythonhosted.org
traceroute to files.pythonhosted.org (2a04:4e42:8d::319), 30 hops max, 80 byte packets
connect: Network is unreachable
```


### HTTPS Requests / IPv4

```console (paste your output after the line with the curl command)
$ curl -vvv -I --ipv4 https://pypi.org/pypi/pip/json
*   Trying 151.101.192.223:443...
* Connected to pypi.org (151.101.192.223) port 443 (#0)
* ALPN, offering h2
* ALPN, offering http/1.1
*  CAfile: /etc/ssl/certs/ca-certificates.crt
*  CApath: /etc/ssl/certs
* TLSv1.0 (OUT), TLS header, Certificate Status (22):
* TLSv1.3 (OUT), TLS handshake, Client hello (1):
* SSL connection timeout
* Closing connection 0
curl: (28) SSL connection timeout
```

```console (paste your output after the line with the curl command)
$ curl -vvv -I --ipv4 https://files.pythonhosted.org/packages/ae/e8/2340d46ecadb1692a1e455f13f75e596d4eab3d11a57446f08259dee8f02/pip-10.0.1.tar.gz
*   Trying 146.75.117.63:443...
* Connected to files.pythonhosted.org (146.75.117.63) port 443 (#0)
* ALPN, offering h2
* ALPN, offering http/1.1
*  CAfile: /etc/ssl/certs/ca-certificates.crt
*  CApath: /etc/ssl/certs
* TLSv1.0 (OUT), TLS header, Certificate Status (22):
* TLSv1.3 (OUT), TLS handshake, Client hello (1):
* OpenSSL SSL_connect: Connection reset by peer in connection to files.pythonhosted.org:443
* Closing connection 0
* TLSv1.0 (OUT), TLS header, Unknown (21):
* TLSv1.3 (OUT), TLS alert, decode error (562):
curl: (35) OpenSSL SSL_connect: Connection reset by peer in connection to files.pythonhosted.org:443
```


### HTTPS Requests / IPv6 (If available)

```console (paste your output after the line with the curl command)
$ curl -vvv -I --ipv6 https://pypi.org/pypi/pip/json
*   Trying 2a04:4e42::223:443...
* Immediate connect fail for 2a04:4e42::223: Network is unreachable
*   Trying 2a04:4e42:400::223:443...
* Immediate connect fail for 2a04:4e42:400::223: Network is unreachable
*   Trying 2a04:4e42:200::223:443...
* Immediate connect fail for 2a04:4e42:200::223: Network is unreachable
*   Trying 2a04:4e42:600::223:443...
* Immediate connect fail for 2a04:4e42:600::223: Network is unreachable
* Closing connection 0
curl: (7) Couldn't connect to server
```

```console (paste your output after the line with the curl command)
$ curl -vvv -I --ipv6 https://files.pythonhosted.org/packages/ae/e8/2340d46ecadb1692a1e455f13f75e596d4eab3d11a57446f08259dee8f02/pip-10.0.1.tar.gz
*   Trying 2a04:4e42:8d::319:443...
* Immediate connect fail for 2a04:4e42:8d::319: Network is unreachable
* Closing connection 0
curl: (7) Couldn't connect to server
```


### TLS Debug / IPv4

```console (paste your output after the line with the openssl command)
$ echo -n | openssl s_client -4 -connect pypi.org:443
CONNECTED(00000003)
```
and stays open afterwards...

```console (paste your output after the line with the openssl command)
$ echo -n | openssl s_client -4 -connect files.pythonhosted.org:443
CONNECTED(00000003)
```
and stays open afterwards...


### TLS Debug / IPv6 (If available)

```console (paste your output after the line with the openssl command)
$ echo -n | openssl s_client -6 -connect pypi.org:443
40073E1EC37F0000:error:80000065:system library:BIO_connect:Network is unreachable:../crypto/bio/bio_sock2.c:125:calling connect()
40073E1EC37F0000:error:10000067:BIO routines:BIO_connect:connect error:../crypto/bio/bio_sock2.c:127:
40073E1EC37F0000:error:80000065:system library:BIO_connect:Network is unreachable:../crypto/bio/bio_sock2.c:125:calling connect()
40073E1EC37F0000:error:10000067:BIO routines:BIO_connect:connect error:../crypto/bio/bio_sock2.c:127:
40073E1EC37F0000:error:80000065:system library:BIO_connect:Network is unreachable:../crypto/bio/bio_sock2.c:125:calling connect()
40073E1EC37F0000:error:10000067:BIO routines:BIO_connect:connect error:../crypto/bio/bio_sock2.c:127:
40073E1EC37F0000:error:80000065:system library:BIO_connect:Network is unreachable:../crypto/bio/bio_sock2.c:125:calling connect()
40073E1EC37F0000:error:10000067:BIO routines:BIO_connect:connect error:../crypto/bio/bio_sock2.c:127:
connect:errno=101
```

```console (paste your output after the line with the openssl command)
$ echo -n | openssl s_client -6 -connect files.pythonhosted.org:443
406769D4717F0000:error:80000065:system library:BIO_connect:Network is unreachable:../crypto/bio/bio_sock2.c:125:calling connect()
406769D4717F0000:error:10000067:BIO routines:BIO_connect:connect error:../crypto/bio/bio_sock2.c:127:
connect:errno=101
```


### Code of Conduct

- [X] I agree to follow the PSF Code of Conduct

Provide feedback

Saved searches

Use saved searches to filter your results more quickly

Uh oh!

Cannot install packages with pip - timeout error #2409

My Platform

Fastly Debug

DNS Resolution

Traceroutes / IPv4

Traceroutes / IPv6 (If available)

HTTPS Requests / IPv4

HTTPS Requests / IPv6 (If available)

TLS Debug / IPv4

TLS Debug / IPv6 (If available)

Code of Conduct

Metadata

Assignees

Labels

Projects

Milestone

Relationships

Development

Cannot install packages with pip - timeout error #2409

Description

My Platform

Fastly Debug

DNS Resolution

Traceroutes / IPv4

Traceroutes / IPv6 (If available)

HTTPS Requests / IPv4

HTTPS Requests / IPv6 (If available)

TLS Debug / IPv4

TLS Debug / IPv6 (If available)

Code of Conduct

Metadata

Metadata

Assignees

Labels

Projects

Milestone

Relationships

Development

Issue actions