diff --git a/.riot/requirements/14a7a5f.txt b/.riot/requirements/14a7a5f.txt
deleted file mode 100644
index 47926643d1d..00000000000
--- a/.riot/requirements/14a7a5f.txt
+++ /dev/null
@@ -1,53 +0,0 @@
-#
-# This file is autogenerated by pip-compile with Python 3.15
-# by the following command:
-#
-#    pip-compile --allow-unsafe --no-annotate .riot/requirements/14a7a5f.in
-#
-annotated-types==0.7.0
-anyio==4.13.0
-attrs==26.1.0
-certifi==2026.5.20
-colorama==0.4.6
-coverage[toml]==7.14.0
-distro==1.9.0
-eval-type-backport==0.3.1
-genai-prices==0.0.61
-griffe==2.0.2
-griffecli==2.0.2
-griffelib==2.0.2
-h11==0.16.0
-httpcore==1.0.9
-httpx==0.28.1
-hypothesis==6.45.0
-idna==3.15
-iniconfig==2.3.0
-jiter==0.15.0
-logfire-api==4.33.0
-mock==5.2.0
-multidict==6.7.1
-openai==2.37.0
-opentelemetry-api==1.42.0
-opentracing==2.4.0
-packaging==26.2
-pluggy==1.6.0
-propcache==0.5.2
-pydantic==2.12.0a1
-pydantic-ai-slim[openai]==0.8.1
-pydantic-core==2.37.2
-pydantic-graph==0.8.1
-pygments==2.20.0
-pytest==9.0.3
-pytest-asyncio==1.3.0
-pytest-cov==7.1.0
-pytest-mock==3.15.1
-pyyaml==6.0.3
-sniffio==1.3.1
-sortedcontainers==2.4.0
-tqdm==4.67.3
-typing-extensions==4.15.0
-typing-inspection==0.4.2
-urllib3==2.7.0
-vcrpy==7.0.0
-wrapt==2.1.2
-yarl==1.24.2
diff --git a/.riot/requirements/1f96562.txt b/.riot/requirements/1f96562.txt
deleted file mode 100644
index cb0e3c5dec7..00000000000
--- a/.riot/requirements/1f96562.txt
+++ /dev/null
@@ -1,53 +0,0 @@
-#
-# This file is autogenerated by pip-compile with Python 3.15
-# by the following command:
-#
-#    pip-compile --allow-unsafe --no-annotate .riot/requirements/1f96562.in
-#
-annotated-types==0.7.0
-anyio==4.13.0
-attrs==26.1.0
-certifi==2026.5.20
-colorama==0.4.6
-coverage[toml]==7.14.0
-distro==1.9.0
-eval-type-backport==0.3.1
-genai-prices==0.0.61
-griffe==2.0.2
-griffecli==2.0.2
-griffelib==2.0.2
-h11==0.16.0
-httpcore==1.0.9
-httpx==0.28.1
-hypothesis==6.45.0
-idna==3.15
-iniconfig==2.3.0
-jiter==0.15.0
-logfire-api==4.33.0
-mock==5.2.0
-multidict==6.7.1
-openai==2.37.0
-opentelemetry-api==1.42.0
-opentracing==2.4.0
-packaging==26.2
-pluggy==1.6.0
-propcache==0.5.2
-pydantic==2.12.0a1
-pydantic-ai-slim[openai]==1.0.0
-pydantic-core==2.37.2
-pydantic-graph==1.0.0
-pygments==2.20.0
-pytest==9.0.3
-pytest-asyncio==1.3.0
-pytest-cov==7.1.0
-pytest-mock==3.15.1
-pyyaml==6.0.3
-sniffio==1.3.1
-sortedcontainers==2.4.0
-tqdm==4.67.3
-typing-extensions==4.15.0
-typing-inspection==0.4.2
-urllib3==2.7.0
-vcrpy==7.0.0
-wrapt==2.1.2
-yarl==1.24.2
diff --git a/ddtrace/contrib/internal/pytest/_plugin_v2.py b/ddtrace/contrib/internal/pytest/_plugin_v2.py
index b15db745c17..e380236a7f1 100644
--- a/ddtrace/contrib/internal/pytest/_plugin_v2.py
+++ b/ddtrace/contrib/internal/pytest/_plugin_v2.py
@@ -66,6 +66,7 @@
 from ddtrace.internal.ci_visibility.utils import take_over_logger_stream_handler
 from ddtrace.internal.coverage.code import ModuleCodeCollector
 from ddtrace.internal.coverage.installer import install as install_coverage
+from ddtrace.internal.coverage.instrumentation import deregister_monitoring
 from ddtrace.internal.logger import get_logger
 from ddtrace.internal.settings import env
 from ddtrace.internal.settings.asm import config as asm_config
@@ -507,6 +508,13 @@ def pytest_unconfigure(config: pytest_Config) -> None:
 def pytest_sessionstart(session: pytest.Session) -> None:
     # Reset stale coverage state from any previous in-process session (e.g. pytester.inline_run)
     reset_coverage_state()
+    # If pytest-cov is enabled for this session, release sys.monitoring.COVERAGE_ID now so that
+    # pytest-cov can claim it in pytest_load_initial_conftests (which runs after sessionstart).
+    # This only matters when a previous in-process session left us holding COVERAGE_ID; in a fresh
+    # process ddtrace registers lazily during test execution, so pytest-cov always wins the race.
+    # If we need COVERAGE_ID again later, instrument_all_lines() re-registers it lazily.
+    if _is_pytest_cov_enabled(session.config):
+        deregister_monitoring()
 
     if not is_test_visibility_enabled():
         return
diff --git a/ddtrace/internal/bytecode_injection/__init__.py b/ddtrace/internal/bytecode_injection/__init__.py
index 661ca193904..97e3cc23341 100644
--- a/ddtrace/internal/bytecode_injection/__init__.py
+++ b/ddtrace/internal/bytecode_injection/__init__.py
@@ -30,7 +30,7 @@ class InvalidLine(Exception):
 
 INJECTION_ASSEMBLY = Assembly()
 if PY >= (3, 15):
-    raise NotImplementedError("Python >= 3.15 is not supported yet")
+    pass  # AIDEV-TODO: Populate assembly for 3.15 bytecode (tracked in #17849).
 elif PY >= (3, 13):
     INJECTION_ASSEMBLY.parse(
         r"""
diff --git a/ddtrace/internal/coverage/instrumentation.py b/ddtrace/internal/coverage/instrumentation.py
index 7dc7fa2b6f8..ea075658177 100644
--- a/ddtrace/internal/coverage/instrumentation.py
+++ b/ddtrace/internal/coverage/instrumentation.py
@@ -3,12 +3,25 @@
 
 # Import are noqa'd otherwise some formatters will helpfully remove them
 if sys.version_info >= (3, 16):
+    from ddtrace.internal.coverage.instrumentation_py3_16 import deregister_monitoring  # noqa
     from ddtrace.internal.coverage.instrumentation_py3_16 import instrument_all_lines  # noqa
 elif sys.version_info >= (3, 12):
+    from ddtrace.internal.coverage.instrumentation_py3_12 import deregister_monitoring  # noqa
     from ddtrace.internal.coverage.instrumentation_py3_12 import instrument_all_lines  # noqa
 elif sys.version_info >= (3, 11):
     from ddtrace.internal.coverage.instrumentation_py3_11 import instrument_all_lines  # noqa
+
+    def deregister_monitoring() -> None:  # noqa: E306
+        pass  # sys.monitoring not available on Python < 3.12
+
 elif sys.version_info >= (3, 10):
     from ddtrace.internal.coverage.instrumentation_py3_10 import instrument_all_lines  # noqa
+
+    def deregister_monitoring() -> None:  # noqa: E306
+        pass  # sys.monitoring not available on Python < 3.12
+
 else:
     from ddtrace.internal.coverage.instrumentation_py3_9 import instrument_all_lines  # noqa
+
+    def deregister_monitoring() -> None:  # noqa: E306
+        pass  # sys.monitoring not available on Python < 3.12
diff --git a/ddtrace/internal/coverage/instrumentation_py3_12.py b/ddtrace/internal/coverage/instrumentation_py3_12.py
index 3a394f7a1ce..cadc9cfcf1e 100644
--- a/ddtrace/internal/coverage/instrumentation_py3_12.py
+++ b/ddtrace/internal/coverage/instrumentation_py3_12.py
@@ -130,6 +130,20 @@ def _register_monitoring():
     sys.monitoring.register_callback(sys.monitoring.COVERAGE_ID, EVENT, _event_handler)
 
 
+def deregister_monitoring() -> None:
+    """Release sys.monitoring.COVERAGE_ID if currently held by datadog.
+
+    Called at the start of each new in-process pytest session (e.g. pytester.inline_run)
+    so that another coverage tool such as pytest-cov can claim COVERAGE_ID without
+    hitting "ValueError: tool 1 is already in use".  The next instrumentation call
+    will re-register us if coverage is still needed.
+    """
+    if sys.monitoring.get_tool(sys.monitoring.COVERAGE_ID) == "datadog":
+        sys.monitoring.register_callback(sys.monitoring.COVERAGE_ID, EVENT, None)
+        sys.monitoring.free_tool_id(sys.monitoring.COVERAGE_ID)
+        _CODE_HOOKS.clear()
+
+
 def _instrument_with_monitoring(
     code: CodeType, hook: HookType, path: str, package: str
 ) -> tuple[CodeType, CoverageLines]:
diff --git a/ddtrace/internal/coverage/instrumentation_py3_16.py b/ddtrace/internal/coverage/instrumentation_py3_16.py
index 2c663719e28..550b9193220 100644
--- a/ddtrace/internal/coverage/instrumentation_py3_16.py
+++ b/ddtrace/internal/coverage/instrumentation_py3_16.py
@@ -18,3 +18,8 @@
 def instrument_all_lines(code: CodeType, hook: HookType, path: str, package: str) -> tuple[CodeType, CoverageLines]:
     # No-op
     return code, CoverageLines()
+
+
+def deregister_monitoring() -> None:
+    # No-op: instrumentation is not yet implemented for Python 3.16+
+    pass
diff --git a/ddtrace/internal/wrapping/asyncs.py b/ddtrace/internal/wrapping/asyncs.py
index 06dc4507f12..020733d59e5 100644
--- a/ddtrace/internal/wrapping/asyncs.py
+++ b/ddtrace/internal/wrapping/asyncs.py
@@ -36,7 +36,7 @@
 ASYNC_HEAD_ASSEMBLY = None
 
 if PY >= (3, 15):
-    raise NotImplementedError("This version of CPython is not supported yet")
+    pass  # AIDEV-TODO: Populate assemblies for 3.15 bytecode (tracked in #17849).
 
 elif PY >= (3, 14):
     ASYNC_HEAD_ASSEMBLY = Assembly()
@@ -712,6 +712,10 @@
 
 
 def wrap_async(instrs: list[bc.Instr], code: CodeType, lineno: int) -> None:
+    if PY >= (3, 15):
+        # AIDEV-TODO: Async wrapping not yet implemented for 3.15; no-op until
+        # #17849 lands. Remove this guard once the assemblies above are populated.
+        return
     if (bc.CompilerFlags.ASYNC_GENERATOR | bc.CompilerFlags.COROUTINE) & code.co_flags:
         if ASYNC_HEAD_ASSEMBLY is not None:
             instrs[0:0] = ASYNC_HEAD_ASSEMBLY.bind(lineno=lineno)
diff --git a/ddtrace/internal/wrapping/context.py b/ddtrace/internal/wrapping/context.py
index 62043667412..6cc8c54831a 100644
--- a/ddtrace/internal/wrapping/context.py
+++ b/ddtrace/internal/wrapping/context.py
@@ -79,7 +79,9 @@
 CONTEXT_FOOT = Assembly()
 
 if sys.version_info >= (3, 15):
-    raise NotImplementedError("Python >= 3.15 is not supported yet")
+    # AIDEV-TODO: Populate assemblies for 3.15 bytecode (tracked in #17849).
+    # Define the stub so references below don't NameError.
+    CONTEXT_RETURN_CONST: Assembly = Assembly()
 elif sys.version_info >= (3, 13):
     CONTEXT_HEAD.parse(
         r"""
@@ -587,7 +589,17 @@ def extract(cls, f: FunctionType) -> "_UniversalWrappingContext":
             raise ValueError("Function is not wrapped")
         return t.cast(_UniversalWrappingContext, t.cast(ContextWrappedFunction, f).__dd_context_wrapped__)
 
-    if sys.version_info >= (3, 11):
+    if sys.version_info >= (3, 15):
+
+        def wrap(self) -> None:
+            # AIDEV-TODO: No-op until #17849 implements wrapping for 3.15.
+            pass
+
+        def unwrap(self) -> None:
+            # AIDEV-TODO: No-op until #17849 implements wrapping for 3.15.
+            pass
+
+    elif sys.version_info >= (3, 11):
 
         def wrap(self) -> None:
             f = self.__wrapped__
diff --git a/ddtrace/internal/wrapping/generators.py b/ddtrace/internal/wrapping/generators.py
index 7406f978cbc..8b12b472254 100644
--- a/ddtrace/internal/wrapping/generators.py
+++ b/ddtrace/internal/wrapping/generators.py
@@ -34,7 +34,7 @@
 GENERATOR_HEAD_ASSEMBLY = None
 
 if PY >= (3, 15):
-    raise NotImplementedError("This version of CPython is not supported yet")
+    pass  # AIDEV-TODO: Populate assemblies for 3.15 bytecode (tracked in #17849).
 
 elif PY >= (3, 14):
     GENERATOR_HEAD_ASSEMBLY = Assembly()
@@ -485,6 +485,9 @@
 
 
 def wrap_generator(instrs: list[bc.Instr], code: CodeType, lineno: int) -> None:
+    if PY >= (3, 15):
+        # AIDEV-TODO: No-op until #17849 populates the assemblies above.
+        return
     if GENERATOR_HEAD_ASSEMBLY is not None:
         instrs[0:0] = GENERATOR_HEAD_ASSEMBLY.bind(lineno=lineno)
 
diff --git a/ddtrace/testing/internal/pytest/plugin.py b/ddtrace/testing/internal/pytest/plugin.py
index f9b3872a821..e29a05b906b 100644
--- a/ddtrace/testing/internal/pytest/plugin.py
+++ b/ddtrace/testing/internal/pytest/plugin.py
@@ -19,6 +19,7 @@
 from ddtrace.contrib.internal.coverage.utils import _is_pytest_cov_enabled
 from ddtrace.contrib.internal.coverage.utils import handle_coverage_report
 from ddtrace.internal.ci_visibility.utils import get_source_lines_for_test_method
+from ddtrace.internal.coverage.instrumentation import deregister_monitoring
 from ddtrace.internal.settings import env
 from ddtrace.internal.utils.inspection import undecorated
 from ddtrace.testing.internal.ci import CITag
@@ -275,6 +276,13 @@ def pytest_sessionstart(self, session: pytest.Session) -> None:
         if session.config.getoption("ddtrace-patch-all"):
             self.enable_all_ddtrace_integrations = True
 
+        # If pytest-cov is enabled for this session, release sys.monitoring.COVERAGE_ID so
+        # that pytest-cov can claim it in pytest_load_initial_conftests (which runs after
+        # sessionstart). Required when a previous in-process session (e.g. pytester.inline_run)
+        # left us holding the slot; instrument_all_lines() re-registers it lazily if needed.
+        if _is_pytest_cov_enabled(session.config):
+            deregister_monitoring()
+
         self.session.start()
         self.manager.start()
 
diff --git a/riotfile.py b/riotfile.py
index 3eb68f7d9b5..30da8c9b4db 100644
--- a/riotfile.py
+++ b/riotfile.py
@@ -3215,7 +3215,9 @@ def select_pys(min_version: str = MIN_PYTHON_VERSION, max_version: str = MAX_PYT
                     },
                 ),
                 Venv(
-                    pys=select_pys(min_version="3.10"),
+                    # pydantic==2.12.0a1 requires pydantic-core~=2.37.x which uses
+                    # PyO3 0.25.x — capped at 3.14 since PyO3 0.25.x doesn't support 3.15+.
+                    pys=select_pys(min_version="3.10", max_version="3.14"),
                     pkgs={
                         "pydantic-ai-slim[openai]": ["==0.8.1", "==1.0.0"],
                         "pydantic": "==2.12.0a1",
diff --git a/tested_versions.json b/tested_versions.json
index d97c3589009..47f6b475e94 100644
--- a/tested_versions.json
+++ b/tested_versions.json
@@ -4047,14 +4047,6 @@
           "version": "1.63.0",
           "python_version": "3.14"
         },
-        {
-          "version": "0.8.1",
-          "python_version": "3.15"
-        },
-        {
-          "version": "1.0.0",
-          "python_version": "3.15"
-        },
         {
           "version": "1.63.0",
           "python_version": "3.15"
diff --git a/tests/conftest.py b/tests/conftest.py
index ae6c346b181..57df25e04f5 100644
--- a/tests/conftest.py
+++ b/tests/conftest.py
@@ -210,7 +210,7 @@ def use_dummy_writer():
 def auto_enable_crashtracking():
     # Crashtracking is only supported on linux right now
     # TODO: Default to `True` when Windows and Darwin are supported
-    yield platform.system() == "Linux"
+    yield platform.system() == "Linux" and crashtracking.is_available
 
 
 @pytest.fixture(autouse=True)
diff --git a/tests/smoke_test.py b/tests/smoke_test.py
index ddd71fbeea2..a06da19ca50 100644
--- a/tests/smoke_test.py
+++ b/tests/smoke_test.py
@@ -76,7 +76,8 @@ def emit(self, record):
         print("Skipping test, 32-bit DDWAF not ready yet")
 
     # Profiling smoke test
-    if platform.system() in ("Linux", "Darwin") and sys.maxsize > (1 << 32):
+    # Profiling extensions are not built for Python 3.15+ (see setup.py, tracked in #17817)
+    if platform.system() in ("Linux", "Darwin") and sys.maxsize > (1 << 32) and sys.version_info < (3, 15):
         print("Running profiling smoke test...")
         profiling_cmd = [sys.executable, "-c", "import ddtrace.profiling.auto"]
         result = subprocess.run(profiling_cmd, capture_output=True, text=True)
diff --git a/tests/testing/internal/pytest/test_pytest_itr.py b/tests/testing/internal/pytest/test_pytest_itr.py
index 809dcd07930..54b483161d6 100644
--- a/tests/testing/internal/pytest/test_pytest_itr.py
+++ b/tests/testing/internal/pytest/test_pytest_itr.py
@@ -290,7 +290,6 @@ def test_should_run():
         assert session["content"]["metrics"]["test.itr.tests_skipping.count"] == 1
 
     @pytest.mark.skipif("slipcover" in sys.modules, reason="slipcover is incompatible with ITR code coverage")
-    @pytest.mark.skipif(sys.version_info >= (3, 14), reason="ITR code coverage currently not supported in Python 3.14")
     def test_itr_code_coverage_enabled(self, pytester: Pytester) -> None:
         pytester.makepyfile(
             lib_constants="""
@@ -318,7 +317,6 @@ def test_answer():
         assert covered_files == {"/test_foo.py", "/lib_constants.py"}
 
     @pytest.mark.skipif("slipcover" in sys.modules, reason="slipcover is incompatible with ITR code coverage")
-    @pytest.mark.skipif(sys.version_info >= (3, 14), reason="ITR code coverage currently not supported in Python 3.14")
     def test_itr_code_coverage_disabled(self, pytester: Pytester) -> None:
         pytester.makepyfile(
             lib_constants="""
diff --git a/tests/testing/test_integration.py b/tests/testing/test_integration.py
index 61b1d5c9300..d64e08cbdc6 100644
--- a/tests/testing/test_integration.py
+++ b/tests/testing/test_integration.py
@@ -1,11 +1,13 @@
 #!/usr/bin/env python3
 
 import os
+import sys
 from unittest.mock import Mock
 from unittest.mock import patch
 
 from _pytest.monkeypatch import MonkeyPatch
 from _pytest.pytester import Pytester
+import pytest
 
 from ddtrace.testing.internal.session_manager import SessionManager
 from ddtrace.testing.internal.test_data import ModuleRef
@@ -491,6 +493,10 @@ def test_simple_pass():
         result.assert_outcomes(passed=2)
 
 
+@pytest.mark.skipif(
+    sys.version_info >= (3, 15),
+    reason="IAST taint-tracking native extension not built for Python 3.15+ (setup.py, tracked in IAST 3.15 issue)",
+)
 class TestIASTTerminalSummary:
     def test_ddtrace_iast_terminal_summary_enabled(self, pytester: Pytester, monkeypatch: MonkeyPatch) -> None:
         """Test that IAST terminal summary is present when IAST is enabled."""