diff --git a/Makefile b/Makefile
index 5b57ba281..49ab59857 100644
--- a/Makefile
+++ b/Makefile
@@ -178,8 +178,8 @@ develop:
 # Then start installing our deps so they can be cached. Note that use of --build-options / --global-options / --install-options
 # disables the cache.
 # We need wheel>=0.26 on Python 3.5. See previous revisions.
-	time ${PYTHON} -m pip install -U -r ci-requirements.txt
-	GEVENTSETUP_EV_VERIFY=3 time ${PYTHON} -m pip install -U -e .[test,dnspython,events]
+	time ${PYTHON} -m pip install -U --upgrade-strategy=eager -r ci-requirements.txt
+	GEVENTSETUP_EV_VERIFY=3 time ${PYTHON} -m pip install -U --upgrade-strategy=eager -e .[test,dnspython,events]
 	${PYTHON} -m pip freeze
 	ccache -s
 	@${PYTHON} scripts/travis.py fold_end install
diff --git a/appveyor.yml b/appveyor.yml
index 98d16806f..ae74d25d0 100644
--- a/appveyor.yml
+++ b/appveyor.yml
@@ -124,7 +124,7 @@ install:
   # compiled extensions and are not provided as pre-built wheel packages,
   # pip will build them from source using the MSVC compiler matching the
   # target Python version and architecture
-  - "%CMD_IN_ENV% %PYEXE% -m pip install -U -r ci-requirements.txt"
+  - "%CMD_IN_ENV% %PYEXE% -m pip install -U --upgrade-strategy=eager -r ci-requirements.txt"
 
   - ps: "if(Test-Path(\"${env:PYTHON}\\bin\")) {ls ${env:PYTHON}\\bin;}"
   - ps: "if(Test-Path(\"${env:PYTHON}\\Scripts\")) {ls ${env:PYTHON}\\Scripts;}"
@@ -142,7 +142,7 @@ build_script:
   # into a variable, using python to glob.
   - "%PYEXE% -c \"import glob; print(glob.glob('dist/*whl')[0])\" > whl.txt"
   - set /p PYWHL=<whl.txt
-  - "%PYEXE% -m pip install %PYWHL%[test,events,dnspython]"
+  - "%PYEXE% -m pip install -U --upgrade-strategy=eager %PYWHL%[test,events,dnspython]"
 
 test_script:
   # Run the project tests