diff --git a/test/fixtures/nltk/runtime.txt b/test/fixtures/nltk/runtime.txt
deleted file mode 100644
index 1935e97..0000000
--- a/test/fixtures/nltk/runtime.txt
+++ /dev/null
@@ -1 +0,0 @@
-python-3.6.6
diff --git a/test/fixtures/pypy2_7_warn/runtime.txt b/test/fixtures/pypy2_7_warn/runtime.txt
index c502b68..e3d29d3 100644
--- a/test/fixtures/pypy2_7_warn/runtime.txt
+++ b/test/fixtures/pypy2_7_warn/runtime.txt
@@ -1 +1 @@
-pypy2.7-7.2.0
+pypy2.7-7.3.1
diff --git a/test/fixtures/pypy3_6_warn/runtime.txt b/test/fixtures/pypy3_6_warn/runtime.txt
index e1af38f..af949aa 100644
--- a/test/fixtures/pypy3_6_warn/runtime.txt
+++ b/test/fixtures/pypy3_6_warn/runtime.txt
@@ -1 +1 @@
-pypy3.6-7.2.0
+pypy3.6-7.3.1
diff --git a/test/fixtures/python2_warn/requirements.txt b/test/fixtures/python2_warn/requirements.txt
index 663bd1f..e69de29 100644
--- a/test/fixtures/python2_warn/requirements.txt
+++ b/test/fixtures/python2_warn/requirements.txt
@@ -1 +0,0 @@
-requests
\ No newline at end of file
diff --git a/test/fixtures/python3_4_warn/requirements.txt b/test/fixtures/python3_4_warn/requirements.txt
index 7e10602..e69de29 100644
--- a/test/fixtures/python3_4_warn/requirements.txt
+++ b/test/fixtures/python3_4_warn/requirements.txt
@@ -1 +0,0 @@
-flask
diff --git a/test/fixtures/python3_5_warn/requirements.txt b/test/fixtures/python3_5_warn/requirements.txt
index 7e10602..e69de29 100644
--- a/test/fixtures/python3_5_warn/requirements.txt
+++ b/test/fixtures/python3_5_warn/requirements.txt
@@ -1 +0,0 @@
-flask
diff --git a/test/fixtures/python3_6/runtime.txt b/test/fixtures/python3_6/runtime.txt
index 9fbd3bf..4252f10 100644
--- a/test/fixtures/python3_6/runtime.txt
+++ b/test/fixtures/python3_6/runtime.txt
@@ -1 +1 @@
-python-3.6.8
+python-3.6.12
diff --git a/test/fixtures/python3_6_warn/requirements.txt b/test/fixtures/python3_6_warn/requirements.txt
index 663bd1f..e69de29 100644
--- a/test/fixtures/python3_6_warn/requirements.txt
+++ b/test/fixtures/python3_6_warn/requirements.txt
@@ -1 +0,0 @@
-requests
\ No newline at end of file
diff --git a/test/fixtures/python3_7/runtime.txt b/test/fixtures/python3_7/runtime.txt
index a01373a..795ee72 100644
--- a/test/fixtures/python3_7/runtime.txt
+++ b/test/fixtures/python3_7/runtime.txt
@@ -1 +1 @@
-python-3.7.2
+python-3.7.9
diff --git a/test/fixtures/python3_7_warn/requirements.txt b/test/fixtures/python3_7_warn/requirements.txt
index 663bd1f..e69de29 100644
--- a/test/fixtures/python3_7_warn/requirements.txt
+++ b/test/fixtures/python3_7_warn/requirements.txt
@@ -1 +0,0 @@
-requests
\ No newline at end of file
diff --git a/test/fixtures/python3_8/runtime.txt b/test/fixtures/python3_8/runtime.txt
index 724c203..0fd6938 100644
--- a/test/fixtures/python3_8/runtime.txt
+++ b/test/fixtures/python3_8/runtime.txt
@@ -1 +1 @@
-python-3.8.2
+python-3.8.6
diff --git a/test/fixtures/python3_8_warn/requirements.txt b/test/fixtures/python3_8_warn/requirements.txt
index f229360..e69de29 100644
--- a/test/fixtures/python3_8_warn/requirements.txt
+++ b/test/fixtures/python3_8_warn/requirements.txt
@@ -1 +0,0 @@
-requests
diff --git a/test/fixtures/pythonDefault/requirements.txt b/test/fixtures/pythonDefault/requirements.txt
deleted file mode 100644
index 7e10602..0000000
--- a/test/fixtures/pythonDefault/requirements.txt
+++ /dev/null
@@ -1 +0,0 @@
-flask
diff --git a/test/fixtures/no-runtime-txt/requirements.txt b/test/fixtures/python_version_unspecified/requirements.txt
similarity index 100%
rename from test/fixtures/no-runtime-txt/requirements.txt
rename to test/fixtures/python_version_unspecified/requirements.txt
diff --git a/test/run-deps b/test/run-deps
index 551d21e..8b69f2a 100755
--- a/test/run-deps
+++ b/test/run-deps
@@ -60,12 +60,6 @@ testPysqlite() {
   assertCapturedSuccess
 }
 
-testSqliteInstall() {
-  compile "pythonDefault"
-  assertNotCaptured "Sqlite3 failed to install."
-  assertCapturedSuccess
-}
-
 testCffi() {
   compile "cffi"
   assertCaptured "cffi"
diff --git a/test/run-features b/test/run-features
index 6a59a76..f67da7b 100755
--- a/test/run-features
+++ b/test/run-features
@@ -59,22 +59,23 @@ testPipenvLock() {
   assertCapturedSuccessWithStdErr
 }
 
-testPipenvVersion() {
+testPipenvPythonVersion3_6() {
   compile "pipenv-version"
-  assertCaptured $DEFAULT_PYTHON_VERSION
+  assertCaptured "Installing ${LATEST_36}"
   # Can't use `assertCapturedSuccess` since stderr contains:
   # "cp: cannot stat '/tmp/build_*/requirements.txt': No such file or directory" (W-7924941)
   assertCapturedSuccessWithStdErr
 }
 
-testPipenvVersion2() {
+testPipenvPythonVersion2_7() {
   compile "pipenv-version2"
-  assertCaptured $LATEST_27
+  assertCaptured "Installing ${LATEST_27}"
   # Can't use `assertCapturedSuccess` since stderr contains:
   # "cp: cannot stat '/tmp/build_*/requirements.txt': No such file or directory" (W-7924941)
   assertCapturedSuccessWithStdErr
 }
-testPipenvFullVersion() {
+
+testPipenvPythonFullVersion() {
   compile "pipenv-full-version"
   assertCaptured "3.6.3"
   # Can't use `assertCapturedSuccess` since stderr contains:
diff --git a/test/run-versions b/test/run-versions
index 82b2f2b..15b6e99 100755
--- a/test/run-versions
+++ b/test/run-versions
@@ -4,42 +4,40 @@
 # shellcheck source=bin/default_pythons
 source "bin/default_pythons"
 
-testPythonDefault() {
-  updateVersion "pythonDefault" $DEFAULT_PYTHON_VERSION
-  compile "pythonDefault"
-  assertCaptured $DEFAULT_PYTHON_VERSION
+testPythonVersionUnspecified() {
+  compile "python_version_unspecified"
+  assertCaptured "Installing ${DEFAULT_PYTHON_VERSION}"
   assertNotCaptured "security update"
   assertCaptured "Installing pip 20.1.1, setuptools 47.1.1 and wheel 0.34.2"
   assertCaptured "Installing SQLite3"
   assertCapturedSuccess
 }
 
-testPython2() {
-    updateVersion "python2" $LATEST_27
-    echo $LATEST_27 > "runtime.txt"
-    compile "python2"
-    assertCaptured $LATEST_27
-    assertCaptured "python-2-7-eol-faq";
-    assertNotCaptured "security update"
-    assertCaptured "Installing pip 20.1.1, setuptools 44.1.1 and wheel 0.34.2"
-    assertCaptured "Installing SQLite3"
-    assertCapturedSuccess
+testPython2_7() {
+  compile "python2"
+  assertCaptured "Installing ${LATEST_27}"
+  assertCaptured "python-2-7-eol-faq";
+  assertNotCaptured "security update"
+  assertCaptured "Installing pip 20.1.1, setuptools 44.1.1 and wheel 0.34.2"
+  assertCaptured "Installing SQLite3"
+  assertCapturedSuccess
 }
 
-testPython2_warn() {
-    compile "python2_warn"
-    assertCaptured "python-2.7.15"
-    assertCaptured "python-2-7-eol-faq";
-    assertCaptured "Only the latest version"
-    assertCaptured "Installing SQLite3"
-    assertCapturedSuccess
+testPython2_7_warn() {
+  compile "python2_warn"
+  assertCaptured "Installing python-2.7.15"
+  assertCaptured "python-2-7-eol-faq";
+  assertCaptured "Only the latest version"
+  assertCaptured "${LATEST_27}"
+  assertCapturedSuccess
 }
 
 testPython3_4() {
   compile "python3_4"
-  assertCaptured $LATEST_34
+  assertCaptured "Installing ${LATEST_34}"
   assertNotCaptured "security update"
   assertCaptured "Installing pip 19.1.1, setuptools 43.0.0 and wheel 0.33.6"
+  assertCaptured "Installing SQLite3"
   # Can't use `assertCapturedSuccess` since Pip outputs a Python 3.4 EOL warning to stderr,
   # and the newest Pip that works on Python 3.4 doesn't support `PIP_NO_PYTHON_VERSION_WARNING`.
   assertCapturedSuccessWithStdErr
@@ -47,8 +45,9 @@ testPython3_4() {
 
 testPython3_4_warn() {
   compile "python3_4_warn"
-  assertCaptured "python-3.4.9"
+  assertCaptured "Installing python-3.4.9"
   assertCaptured "security update!"
+  assertCaptured "${LATEST_34}"
   # Can't use `assertCapturedSuccess` since Pip outputs a Python 3.4 EOL warning to stderr,
   # and the newest Pip that works on Python 3.4 doesn't support `PIP_NO_PYTHON_VERSION_WARNING`.
   assertCapturedSuccessWithStdErr
@@ -56,7 +55,7 @@ testPython3_4_warn() {
 
 testPython3_5() {
   compile "python3_5"
-  assertCaptured $LATEST_35
+  assertCaptured "Installing ${LATEST_35}"
   assertNotCaptured "security update"
   assertCaptured "Installing pip 20.1.1, setuptools 47.1.1 and wheel 0.34.2"
   assertCaptured "Installing SQLite3"
@@ -65,15 +64,15 @@ testPython3_5() {
 
 testPython3_5_warn() {
   compile "python3_5_warn"
-  assertCaptured "python-3.5.6"
+  assertCaptured "Installing python-3.5.6"
   assertCaptured "security update!"
+  assertCaptured "${LATEST_35}"
   assertCapturedSuccess
 }
 
 testPython3_6() {
-  updateVersion "python3_6" $LATEST_36
   compile "python3_6"
-  assertCaptured $LATEST_36
+  assertCaptured "Installing ${LATEST_36}"
   assertNotCaptured "security update"
   assertCaptured "Installing pip 20.1.1, setuptools 47.1.1 and wheel 0.34.2"
   assertCaptured "Installing SQLite3"
@@ -82,62 +81,60 @@ testPython3_6() {
 
 testPython3_6_warn() {
   compile "python3_6_warn"
-  assertCaptured "python-3.6.7"
+  assertCaptured "Installing python-3.6.7"
   assertCaptured "security update!"
-  assertCaptured "Installing SQLite3"
+  assertCaptured "${LATEST_36}"
   assertCapturedSuccess
 }
 
 testPython3_7() {
-  updateVersion "python3_7" $LATEST_37
-  compile "python3_7"
-  if [[ $STACK = "cedar-14" ]]; then
-    assertCapturedError
-  else
-    assertNotCaptured "security update"
-    assertCaptured $LATEST_37
-    assertCaptured "Installing pip 20.1.1, setuptools 47.1.1 and wheel 0.34.2"
-    assertCaptured "Installing SQLite3"
-    assertCapturedSuccess
+  # Python 3.7+ requires newer libssl than is present on Cedar-14.
+  if [[ "${STACK}" = "cedar-14" ]]; then
+    return
   fi
+  compile "python3_7"
+  assertCaptured "Installing ${LATEST_37}"
+  assertNotCaptured "security update"
+  assertCaptured "Installing pip 20.1.1, setuptools 47.1.1 and wheel 0.34.2"
+  assertCaptured "Installing SQLite3"
+  assertCapturedSuccess
 }
 
 testPython3_7_warn() {
-  compile "python3_7_warn"
-  if [[ $STACK = "cedar-14" ]]; then
-    assertCapturedError
-  else
-    assertCaptured "python-3.7.1"
-    assertCaptured "security update!"
-    assertCaptured "Installing SQLite3"
-    assertCapturedSuccess
+  # Python 3.7+ requires newer libssl than is present on Cedar-14.
+  if [[ "${STACK}" = "cedar-14" ]]; then
+    return
   fi
+  compile "python3_7_warn"
+  assertCaptured "Installing python-3.7.1"
+  assertCaptured "security update!"
+  assertCaptured "${LATEST_37}"
+  assertCapturedSuccess
 }
 
 testPython3_8() {
-  updateVersion "python3_8" $LATEST_38
-  compile "python3_8"
-  if [[ $STACK = "cedar-14" ]]; then
-    assertCapturedError
-  else
-    assertNotCaptured "security update"
-    assertCaptured $LATEST_38
-    assertCaptured "Installing pip 20.1.1, setuptools 47.1.1 and wheel 0.34.2"
-    assertCaptured "Installing SQLite3"
-    assertCapturedSuccess
+  # Python 3.7+ requires newer libssl than is present on Cedar-14.
+  if [[ "${STACK}" = "cedar-14" ]]; then
+    return
   fi
+  compile "python3_8"
+  assertCaptured "Installing ${LATEST_38}"
+  assertNotCaptured "security update"
+  assertCaptured "Installing pip 20.1.1, setuptools 47.1.1 and wheel 0.34.2"
+  assertCaptured "Installing SQLite3"
+  assertCapturedSuccess
 }
 
 testPython3_8_warn() {
-  compile "python3_8_warn"
-  if [[ $STACK = "cedar-14" ]]; then
-    assertCapturedError
-  else
-    assertCaptured "python-3.8.0"
-    assertCaptured "security update!"
-    assertCaptured "Installing SQLite3"
-    assertCapturedSuccess
+  # Python 3.7+ requires newer libssl than is present on Cedar-14.
+  if [[ "${STACK}" = "cedar-14" ]]; then
+    return
   fi
+  compile "python3_8_warn"
+  assertCaptured "Installing python-3.8.0"
+  assertCaptured "security update!"
+  assertCaptured "${LATEST_38}"
+  assertCapturedSuccess
 }
 
 testPython3_9() {
@@ -146,8 +143,8 @@ testPython3_9() {
     return
   fi
   compile "python3_9"
+  assertCaptured "Installing ${LATEST_39}"
   assertNotCaptured "security update"
-  assertCaptured $LATEST_39
   assertCaptured "Installing pip 20.1.1, setuptools 47.1.1 and wheel 0.34.2"
   assertCaptured "Installing SQLite3"
   assertCapturedSuccess
@@ -163,8 +160,9 @@ testPython3_9_warn() {
     return
   fi
   compile "python3_9_warn"
-  assertCaptured "python-3.9.0"
+  assertCaptured "Installing python-3.9.0"
   assertCaptured "security update!"
+  assertCaptured "${LATEST_39}"
   assertCapturedSuccess
 }
 
@@ -177,44 +175,34 @@ testPythonVersionInvalid() {
 
 testPypy3_6() {
   compile "pypy3_6"
-  assertCaptured "Installing pypy"
+  assertCaptured "Installing ${LATEST_PYPY_36}"
   assertNotCaptured "security update"
-  assertCaptured "$LATEST_PYPY_36"
   assertCaptured "Installing pip 20.1.1, setuptools 47.1.1 and wheel 0.34.2"
   assertCapturedSuccess
 }
 
 testPypy3_6_warn() {
   compile "pypy3_6_warn"
-  if [[ $STACK = "cedar-14" ]]; then
-    assertCapturedError
-  else
-    assertCaptured "Installing pypy"
-    assertCaptured "security update!"
-    assertCaptured "$LATEST_PYPY_36"
-    assertCapturedSuccess
-  fi
+  assertCaptured "Installing pypy3.6-7.3.1"
+  assertCaptured "security update!"
+  assertCaptured "${LATEST_PYPY_36}"
+  assertCapturedSuccess
 }
 
 testPypy2_7() {
   compile "pypy2_7"
-  assertCaptured "Installing pypy"
+  assertCaptured "Installing ${LATEST_PYPY_27}"
   assertNotCaptured "security update"
-  assertCaptured "$LATEST_PYPY_27"
   assertCaptured "Installing pip 20.1.1, setuptools 44.1.1 and wheel 0.34.2"
   assertCapturedSuccess
 }
 
 testPypy2_7_warn() {
   compile "pypy2_7_warn"
-  if [[ $STACK = "cedar-14" ]]; then
-    assertCapturedError
-  else
-    assertCaptured "Installing pypy"
-    assertCaptured "security update!"
-    assertCaptured "$LATEST_PYPY_27"
-    assertCapturedSuccess
-  fi
+  assertCaptured "Installing pypy2.7-7.3.1"
+  assertCaptured "security update!"
+  assertCaptured "${LATEST_PYPY_27}"
+  assertCapturedSuccess
 }
 
 testStickyPythonVersion() {
@@ -222,8 +210,9 @@ testStickyPythonVersion() {
   compile "python3_6_warn" "$cache_dir"
   assertCaptured "Installing python-3.6.7"
   assertCapturedSuccess
-  compile "no-runtime-txt" "$cache_dir"
-  assertCaptured "Installing python-3.6.7"
+  compile "python_version_unspecified" "$cache_dir"
+  assertNotCaptured "Installing python"
+  assertCaptured "security update!"
   assertCapturedSuccess
   # Whilst this file seems like an implementation detail (so something that should
   # not be tested), we must guarantee the filename remains consistent for backwards
diff --git a/test/utils b/test/utils
index 297a664..af7db6f 100644
--- a/test/utils
+++ b/test/utils
@@ -56,11 +56,6 @@ resetCapture()
   unset rtrn # deprecated
 }
 
-updateVersion()
-{
-  echo "$2" > "test/fixtures/${1}/runtime.txt"
-}
-
 assertCapturedEquals()
 {
   assertEquals "$@" "$(cat ${STD_OUT})"