diff --git a/docs/configuration.md b/docs/configuration.md
index 4ed52b91934..30f8ff55e62 100644
--- a/docs/configuration.md
+++ b/docs/configuration.md
@@ -315,12 +315,15 @@ for more information.
 
 ### `certificates.<name>.cert`:
 
-**Type**: string
+**Type**: string | bool
 
 Set custom certificate authority for repository `<name>`.
 See [Repositories - Configuring credentials - Custom certificate authority]({{< relref "repositories#custom-certificate-authority-and-mutual-tls-authentication" >}})
 for more information.
 
+This configuration can be set to `false`, if TLS certificate verification should be skipped for this
+repository.
+
 ### `certificates.<name>.client-cert`:
 
 **Type**: string
diff --git a/docs/repositories.md b/docs/repositories.md
index 490d78bf785..d356d661953 100644
--- a/docs/repositories.md
+++ b/docs/repositories.md
@@ -384,6 +384,21 @@ poetry config certificates.foo.cert /path/to/ca.pem
 poetry config certificates.foo.client-cert /path/to/client.pem
 ```
 
+{{% note %}}
+The value of `certificates.<repository>.cert` can be set to `false` if certificate verification is
+required to be skipped. This is useful for cases where a package source with self-signed certificates
+are used.
+
+```bash
+poetry config certificates.foo.cert false
+```
+{{% /note %}}
+
+{{% warning %}
+Disabling certificate verification is not recommended as it is does not conform to security
+best practices.
+{{% /warning %}
+
 ## Caches
 
 Poetry employs multiple caches for package sources in order to improve user experience and avoid duplicate network
diff --git a/src/poetry/console/commands/config.py b/src/poetry/console/commands/config.py
index 11ba60d25a3..eacb058573b 100644
--- a/src/poetry/console/commands/config.py
+++ b/src/poetry/console/commands/config.py
@@ -3,6 +3,7 @@
 import json
 import re
 
+from pathlib import Path
 from typing import TYPE_CHECKING
 from typing import Any
 from typing import cast
@@ -11,7 +12,11 @@
 from cleo.helpers import option
 
 from poetry.config.config import PackageFilterPolicy
+from poetry.config.config import boolean_normalizer
+from poetry.config.config import boolean_validator
+from poetry.config.config import int_normalizer
 from poetry.console.commands.command import Command
+from poetry.locations import DEFAULT_CACHE_DIR
 
 
 if TYPE_CHECKING:
@@ -48,13 +53,6 @@ class ConfigCommand(Command):
 
     @property
     def unique_config_values(self) -> dict[str, tuple[Any, Any, Any]]:
-        from pathlib import Path
-
-        from poetry.config.config import boolean_normalizer
-        from poetry.config.config import boolean_validator
-        from poetry.config.config import int_normalizer
-        from poetry.locations import DEFAULT_CACHE_DIR
-
         unique_config_values = {
             "cache-dir": (
                 str,
@@ -275,20 +273,26 @@ def handle(self) -> int | None:
             return 0
 
         # handle certs
-        m = re.match(
-            r"(?:certificates)\.([^.]+)\.(cert|client-cert)", self.argument("key")
-        )
+        m = re.match(r"certificates\.([^.]+)\.(cert|client-cert)", self.argument("key"))
         if m:
+            repository = m.group(1)
+            key = m.group(2)
+
             if self.option("unset"):
                 config.auth_config_source.remove_property(
-                    f"certificates.{m.group(1)}.{m.group(2)}"
+                    f"certificates.{repository}.{key}"
                 )
 
                 return 0
 
             if len(values) == 1:
+                new_value: str | bool = values[0]
+
+                if key == "cert" and boolean_validator(values[0]):
+                    new_value = boolean_normalizer(values[0])
+
                 config.auth_config_source.add_property(
-                    f"certificates.{m.group(1)}.{m.group(2)}", values[0]
+                    f"certificates.{repository}.{key}", new_value
                 )
             else:
                 raise ValueError("You must pass exactly 1 value")
diff --git a/src/poetry/installation/pip_installer.py b/src/poetry/installation/pip_installer.py
index 60acb85b86e..536f6cdce04 100644
--- a/src/poetry/installation/pip_installer.py
+++ b/src/poetry/installation/pip_installer.py
@@ -63,11 +63,17 @@ def install(self, package: Package, update: bool = False) -> None:
                 args += ["--trusted-host", parsed.hostname]
 
             if isinstance(repository, HTTPRepository):
-                if repository.cert:
-                    args += ["--cert", str(repository.cert)]
+                certificates = repository.certificates
 
-                if repository.client_cert:
-                    args += ["--client-cert", str(repository.client_cert)]
+                if certificates.cert:
+                    args += ["--cert", str(certificates.cert)]
+
+                if parsed.scheme == "https" and not certificates.verify:
+                    assert parsed.hostname is not None
+                    args += ["--trusted-host", parsed.hostname]
+
+                if certificates.client_cert:
+                    args += ["--client-cert", str(certificates.client_cert)]
 
                 index_url = repository.authenticated_url
 
diff --git a/src/poetry/publishing/publisher.py b/src/poetry/publishing/publisher.py
index 95f79afdab1..dd31e5c00e3 100644
--- a/src/poetry/publishing/publisher.py
+++ b/src/poetry/publishing/publisher.py
@@ -6,8 +6,6 @@
 
 from poetry.publishing.uploader import Uploader
 from poetry.utils.authenticator import Authenticator
-from poetry.utils.helpers import get_cert
-from poetry.utils.helpers import get_client_cert
 
 
 if TYPE_CHECKING:
@@ -72,9 +70,10 @@ def publish(
                     username = auth.username
                     password = auth.password
 
-        resolved_client_cert = client_cert or get_client_cert(
-            self._poetry.config, repository_name
-        )
+        certificates = self._authenticator.get_certs_for_repository(repository_name)
+        resolved_cert = cert or certificates.cert or certificates.verify
+        resolved_client_cert = client_cert or certificates.client_cert
+
         # Requesting missing credentials but only if there is not a client cert defined.
         if not resolved_client_cert and hasattr(self._io, "ask"):
             if username is None:
@@ -96,7 +95,7 @@ def publish(
 
         self._uploader.upload(
             url,
-            cert=cert or get_cert(self._poetry.config, repository_name),
+            cert=resolved_cert,
             client_cert=resolved_client_cert,
             dry_run=dry_run,
             skip_existing=skip_existing,
diff --git a/src/poetry/publishing/uploader.py b/src/poetry/publishing/uploader.py
index fc60648a5aa..99557561c3f 100644
--- a/src/poetry/publishing/uploader.py
+++ b/src/poetry/publishing/uploader.py
@@ -3,6 +3,7 @@
 import hashlib
 import io
 
+from pathlib import Path
 from typing import TYPE_CHECKING
 from typing import Any
 
@@ -25,8 +26,6 @@
 
 
 if TYPE_CHECKING:
-    from pathlib import Path
-
     from cleo.io.null_io import NullIO
 
     from poetry.poetry import Poetry
@@ -114,15 +113,14 @@ def get_auth(self) -> tuple[str, str] | None:
     def upload(
         self,
         url: str,
-        cert: Path | None = None,
+        cert: Path | bool = True,
         client_cert: Path | None = None,
         dry_run: bool = False,
         skip_existing: bool = False,
     ) -> None:
         session = self.make_session()
 
-        if cert:
-            session.verify = str(cert)
+        session.verify = str(cert) if isinstance(cert, Path) else cert
 
         if client_cert:
             session.cert = str(client_cert)
diff --git a/src/poetry/repositories/http.py b/src/poetry/repositories/http.py
index c453b0cdd7d..8d413b6c0e9 100644
--- a/src/poetry/repositories/http.py
+++ b/src/poetry/repositories/http.py
@@ -31,6 +31,7 @@
 if TYPE_CHECKING:
     from poetry.config.config import Config
     from poetry.inspection.info import PackageInfo
+    from poetry.utils.authenticator import RepositoryCertificateConfig
 
 
 class HTTPRepository(CachedRepository, ABC):
@@ -59,18 +60,8 @@ def url(self) -> str:
         return self._url
 
     @property
-    def cert(self) -> Path | None:
-        cert = self._authenticator.get_certs_for_url(self.url).get("verify")
-        if cert:
-            return Path(cert)
-        return None
-
-    @property
-    def client_cert(self) -> Path | None:
-        cert = self._authenticator.get_certs_for_url(self.url).get("cert")
-        if cert:
-            return Path(cert)
-        return None
+    def certificates(self) -> RepositoryCertificateConfig:
+        return self._authenticator.get_certs_for_url(self.url)
 
     @property
     def authenticated_url(self) -> str:
diff --git a/src/poetry/utils/authenticator.py b/src/poetry/utils/authenticator.py
index ba153111167..81ab081b934 100644
--- a/src/poetry/utils/authenticator.py
+++ b/src/poetry/utils/authenticator.py
@@ -8,6 +8,7 @@
 import urllib.parse
 
 from os.path import commonprefix
+from pathlib import Path
 from typing import TYPE_CHECKING
 from typing import Any
 
@@ -20,21 +21,42 @@
 
 from poetry.config.config import Config
 from poetry.exceptions import PoetryException
-from poetry.utils.helpers import get_cert
-from poetry.utils.helpers import get_client_cert
 from poetry.utils.password_manager import HTTPAuthCredential
 from poetry.utils.password_manager import PasswordManager
 
 
 if TYPE_CHECKING:
-    from pathlib import Path
-
     from cleo.io.io import IO
 
 
 logger = logging.getLogger(__name__)
 
 
+@dataclasses.dataclass(frozen=True)
+class RepositoryCertificateConfig:
+    cert: Path | None = dataclasses.field(default=None)
+    client_cert: Path | None = dataclasses.field(default=None)
+    verify: bool = dataclasses.field(default=True)
+
+    @classmethod
+    def create(
+        cls, repository: str, config: Config | None
+    ) -> RepositoryCertificateConfig:
+        config = config if config else Config.create()
+
+        verify: str | bool = config.get(
+            f"certificates.{repository}.verify",
+            config.get(f"certificates.{repository}.cert", True),
+        )
+        client_cert: str = config.get(f"certificates.{repository}.client-cert")
+
+        return cls(
+            cert=Path(verify) if isinstance(verify, str) else None,
+            client_cert=Path(client_cert) if client_cert else None,
+            verify=verify if isinstance(verify, bool) else True,
+        )
+
+
 @dataclasses.dataclass
 class AuthenticatorRepositoryConfig:
     name: str
@@ -47,11 +69,8 @@ def __post_init__(self) -> None:
         self.netloc = parsed_url.netloc
         self.path = parsed_url.path
 
-    def certs(self, config: Config) -> dict[str, Path | None]:
-        return {
-            "cert": get_client_cert(config, self.name),
-            "verify": get_cert(config, self.name),
-        }
+    def certs(self, config: Config) -> RepositoryCertificateConfig:
+        return RepositoryCertificateConfig.create(self.name, config)
 
     @property
     def http_credential_keys(self) -> list[str]:
@@ -91,7 +110,7 @@ def __init__(
         self._io = io
         self._sessions_for_netloc: dict[str, requests.Session] = {}
         self._credentials: dict[str, HTTPAuthCredential] = {}
-        self._certs: dict[str, dict[str, Path | None]] = {}
+        self._certs: dict[str, RepositoryCertificateConfig] = {}
         self._configured_repositories: dict[
             str, AuthenticatorRepositoryConfig
         ] | None = None
@@ -186,14 +205,13 @@ def request(
         stream = kwargs.get("stream")
 
         certs = self.get_certs_for_url(url)
-        verify = kwargs.get("verify") or certs.get("verify")
-        cert = kwargs.get("cert") or certs.get("cert")
+        verify = kwargs.get("verify") or certs.cert or certs.verify
+        cert = kwargs.get("cert") or certs.client_cert
 
         if cert is not None:
             cert = str(cert)
 
-        if verify is not None:
-            verify = str(verify)
+        verify = str(verify) if isinstance(verify, Path) else verify
 
         settings = session.merge_environment_settings(  # type: ignore[no-untyped-call]
             prepared_request.url, proxies, stream, verify, cert
@@ -332,6 +350,11 @@ def get_http_auth(
             repository=repository, username=username
         )
 
+    def get_certs_for_repository(self, name: str) -> RepositoryCertificateConfig:
+        if name.lower() == "pypi" or name not in self.configured_repositories:
+            return RepositoryCertificateConfig()
+        return self.configured_repositories[name].certs(self._config)
+
     @property
     def configured_repositories(self) -> dict[str, AuthenticatorRepositoryConfig]:
         if self._configured_repositories is None:
@@ -352,7 +375,7 @@ def add_repository(self, name: str, url: str) -> None:
         self.configured_repositories[name] = AuthenticatorRepositoryConfig(name, url)
         self.reset_credentials_cache()
 
-    def get_certs_for_url(self, url: str) -> dict[str, Path | None]:
+    def get_certs_for_url(self, url: str) -> RepositoryCertificateConfig:
         if url not in self._certs:
             self._certs[url] = self._get_certs_for_url(url)
         return self._certs[url]
@@ -398,11 +421,11 @@ def _get_repository_config_for_url(
 
         return candidates[0]
 
-    def _get_certs_for_url(self, url: str) -> dict[str, Path | None]:
+    def _get_certs_for_url(self, url: str) -> RepositoryCertificateConfig:
         selected = self.get_repository_config_for_url(url)
         if selected:
             return selected.certs(config=self._config)
-        return {"cert": None, "verify": None}
+        return RepositoryCertificateConfig()
 
 
 _authenticator: Authenticator | None = None
diff --git a/src/poetry/utils/helpers.py b/src/poetry/utils/helpers.py
index cfc6c3b66b9..69743be2f52 100644
--- a/src/poetry/utils/helpers.py
+++ b/src/poetry/utils/helpers.py
@@ -18,7 +18,6 @@
     from poetry.core.packages.package import Package
     from requests import Session
 
-    from poetry.config.config import Config
     from poetry.utils.authenticator import Authenticator
 
 
@@ -33,22 +32,6 @@ def module_name(name: str) -> str:
     return canonicalize_name(name).replace(".", "_").replace("-", "_")
 
 
-def get_cert(config: Config, repository_name: str) -> Path | None:
-    cert = config.get(f"certificates.{repository_name}.cert")
-    if cert:
-        return Path(cert)
-    else:
-        return None
-
-
-def get_client_cert(config: Config, repository_name: str) -> Path | None:
-    client_cert = config.get(f"certificates.{repository_name}.client-cert")
-    if client_cert:
-        return Path(client_cert)
-    else:
-        return None
-
-
 def _on_rm_error(func: Callable[[str], None], path: str, exc_info: Exception) -> None:
     if not os.path.exists(path):
         return
diff --git a/tests/console/commands/test_config.py b/tests/console/commands/test_config.py
index 2fbca6f1062..052b726c2fd 100644
--- a/tests/console/commands/test_config.py
+++ b/tests/console/commands/test_config.py
@@ -175,16 +175,26 @@ def test_set_client_cert(
     )
 
 
+@pytest.mark.parametrize(
+    ("value", "result"),
+    [
+        ("path/to/ca.pem", "path/to/ca.pem"),
+        ("true", True),
+        ("false", False),
+    ],
+)
 def test_set_cert(
     tester: CommandTester,
     auth_config_source: DictConfigSource,
     mocker: MockerFixture,
+    value: str,
+    result: str | bool,
 ):
     mocker.spy(ConfigSource, "__init__")
 
-    tester.execute("certificates.foo.cert path/to/ca.pem")
+    tester.execute(f"certificates.foo.cert {value}")
 
-    assert auth_config_source.config["certificates"]["foo"]["cert"] == "path/to/ca.pem"
+    assert auth_config_source.config["certificates"]["foo"]["cert"] == result
 
 
 def test_config_installer_parallel(
diff --git a/tests/installation/test_pip_installer.py b/tests/installation/test_pip_installer.py
index 797e7874eba..ec824048a2f 100644
--- a/tests/installation/test_pip_installer.py
+++ b/tests/installation/test_pip_installer.py
@@ -14,6 +14,7 @@
 from poetry.installation.pip_installer import PipInstaller
 from poetry.repositories.legacy_repository import LegacyRepository
 from poetry.repositories.pool import Pool
+from poetry.utils.authenticator import RepositoryCertificateConfig
 from poetry.utils.env import NullEnv
 
 
@@ -21,6 +22,7 @@
     from pytest_mock import MockerFixture
 
     from poetry.utils.env import VirtualEnv
+    from tests.conftest import Config
 
 
 @pytest.fixture
@@ -120,15 +122,15 @@ def test_install_with_non_pypi_default_repository(pool: Pool, installer: PipInst
 @pytest.mark.parametrize(
     ("key", "option"),
     [
-        ("cert", "client-cert"),
-        ("verify", "cert"),
+        ("client_cert", "client-cert"),
+        ("cert", "cert"),
     ],
 )
 def test_install_with_certs(mocker: MockerFixture, key: str, option: str):
     client_path = "path/to/client.pem"
     mocker.patch(
         "poetry.utils.authenticator.Authenticator.get_certs_for_url",
-        return_value={key: client_path},
+        return_value=RepositoryCertificateConfig(**{key: client_path}),
     )
 
     default = LegacyRepository("default", "https://foo.bar")
@@ -204,3 +206,32 @@ def copy_only(source: Path, dest: Path) -> None:
     # any command in the virtual environment should trigger the error message
     output = tmp_venv.run("python", "-m", "site")
     assert not re.match(rf"Error processing line 1 of .*{pth_file}", output)
+
+
+def test_install_with_trusted_host(config: Config):
+    config.merge({"certificates": {"default": {"cert": False}}})
+
+    default = LegacyRepository("default", "https://foo.bar")
+    pool = Pool()
+    pool.add_repository(default, default=True)
+
+    null_env = NullEnv()
+
+    installer = PipInstaller(null_env, NullIO(), pool)
+
+    foo = Package(
+        "foo",
+        "0.0.0",
+        source_type="legacy",
+        source_reference=default.name,
+        source_url=default.url,
+    )
+
+    installer.install(foo)
+
+    assert len(null_env.executed) == 1
+    cmd = null_env.executed[0]
+    assert "--trusted-host" in cmd
+    cert_index = cmd.index("--trusted-host")
+    # Need to do the str(Path()) bit because Windows paths get modified by Path
+    assert cmd[cert_index + 1] == "foo.bar"
diff --git a/tests/publishing/test_publisher.py b/tests/publishing/test_publisher.py
index 2b3cf01c627..afc992f828a 100644
--- a/tests/publishing/test_publisher.py
+++ b/tests/publishing/test_publisher.py
@@ -38,7 +38,7 @@ def test_publish_publishes_to_pypi_by_default(
     assert [("foo", "bar")] == uploader_auth.call_args
     assert [
         ("https://upload.pypi.org/legacy/",),
-        {"cert": None, "client_cert": None, "dry_run": False, "skip_existing": False},
+        {"cert": True, "client_cert": None, "dry_run": False, "skip_existing": False},
     ] == uploader_upload.call_args
 
 
@@ -70,7 +70,7 @@ def test_publish_can_publish_to_given_repository(
     assert [("foo", "bar")] == uploader_auth.call_args
     assert [
         ("http://foo.bar",),
-        {"cert": None, "client_cert": None, "dry_run": False, "skip_existing": False},
+        {"cert": True, "client_cert": None, "dry_run": False, "skip_existing": False},
     ] == uploader_upload.call_args
     assert "Publishing my-package (1.2.3) to foo" in io.fetch_output()
 
@@ -104,7 +104,7 @@ def test_publish_uses_token_if_it_exists(
     assert [("__token__", "my-token")] == uploader_auth.call_args
     assert [
         ("https://upload.pypi.org/legacy/",),
-        {"cert": None, "client_cert": None, "dry_run": False, "skip_existing": False},
+        {"cert": True, "client_cert": None, "dry_run": False, "skip_existing": False},
     ] == uploader_upload.call_args
 
 
@@ -159,7 +159,7 @@ def test_publish_uses_client_cert(
     assert [
         ("https://foo.bar",),
         {
-            "cert": None,
+            "cert": True,
             "client_cert": Path(client_cert),
             "dry_run": False,
             "skip_existing": False,
@@ -186,5 +186,5 @@ def test_publish_read_from_environment_variable(
     assert [("bar", "baz")] == uploader_auth.call_args
     assert [
         ("https://foo.bar",),
-        {"cert": None, "client_cert": None, "dry_run": False, "skip_existing": False},
+        {"cert": True, "client_cert": None, "dry_run": False, "skip_existing": False},
     ] == uploader_upload.call_args
diff --git a/tests/utils/test_authenticator.py b/tests/utils/test_authenticator.py
index 2467959b6f5..aaf560b2064 100644
--- a/tests/utils/test_authenticator.py
+++ b/tests/utils/test_authenticator.py
@@ -16,6 +16,7 @@
 from cleo.io.null_io import NullIO
 
 from poetry.utils.authenticator import Authenticator
+from poetry.utils.authenticator import RepositoryCertificateConfig
 
 
 if TYPE_CHECKING:
@@ -599,3 +600,52 @@ def test_authenticator_git_repositories(
     three = authenticator.get_credentials_for_git_url("https://foo.bar/org/three.git")
     assert not three.username
     assert not three.password
+
+
+@pytest.mark.parametrize(
+    ("ca_cert", "client_cert", "result"),
+    [
+        (None, None, RepositoryCertificateConfig()),
+        (
+            "path/to/ca.pem",
+            "path/to/client.pem",
+            RepositoryCertificateConfig(
+                Path("path/to/ca.pem"), Path("path/to/client.pem")
+            ),
+        ),
+        (
+            None,
+            "path/to/client.pem",
+            RepositoryCertificateConfig(None, Path("path/to/client.pem")),
+        ),
+        (
+            "path/to/ca.pem",
+            None,
+            RepositoryCertificateConfig(Path("path/to/ca.pem"), None),
+        ),
+        (True, None, RepositoryCertificateConfig()),
+        (False, None, RepositoryCertificateConfig(verify=False)),
+        (
+            False,
+            "path/to/client.pem",
+            RepositoryCertificateConfig(None, Path("path/to/client.pem"), verify=False),
+        ),
+    ],
+)
+def test_repository_certificate_configuration_create(
+    ca_cert: str | bool | None,
+    client_cert: str | None,
+    result: RepositoryCertificateConfig,
+    config: Config,
+) -> None:
+    cert_config = {}
+
+    if ca_cert is not None:
+        cert_config["cert"] = ca_cert
+
+    if client_cert is not None:
+        cert_config["client-cert"] = client_cert
+
+    config.merge({"certificates": {"foo": cert_config}})
+
+    assert RepositoryCertificateConfig.create("foo", config) == result
diff --git a/tests/utils/test_helpers.py b/tests/utils/test_helpers.py
index fa452749f0b..7be34c336d5 100644
--- a/tests/utils/test_helpers.py
+++ b/tests/utils/test_helpers.py
@@ -1,19 +1,10 @@
 from __future__ import annotations
 
-from pathlib import Path
-from typing import TYPE_CHECKING
-
 import pytest
 
 from poetry.core.utils.helpers import parse_requires
 
 from poetry.utils.helpers import canonicalize_name
-from poetry.utils.helpers import get_cert
-from poetry.utils.helpers import get_client_cert
-
-
-if TYPE_CHECKING:
-    from tests.conftest import Config
 
 
 def test_parse_requires():
@@ -72,20 +63,6 @@ def test_parse_requires():
     assert result == expected
 
 
-def test_get_cert(config: Config):
-    ca_cert = "path/to/ca.pem"
-    config.merge({"certificates": {"foo": {"cert": ca_cert}}})
-
-    assert get_cert(config, "foo") == Path(ca_cert)
-
-
-def test_get_client_cert(config: Config):
-    client_cert = "path/to/client.pem"
-    config.merge({"certificates": {"foo": {"client-cert": client_cert}}})
-
-    assert get_client_cert(config, "foo") == Path(client_cert)
-
-
 test_canonicalize_name_cases = [
     ("flask", "flask"),
     ("Flask", "flask"),