diff --git a/scripts/populate_tox/config.py b/scripts/populate_tox/config.py
index 7d6a519b6b..70cecd60d9 100644
--- a/scripts/populate_tox/config.py
+++ b/scripts/populate_tox/config.py
@@ -291,6 +291,7 @@
     },
     "requests": {
         "package": "requests",
+        "num_versions": 2,
     },
     "rq": {
         "package": "rq",
diff --git a/scripts/populate_tox/populate_tox.py b/scripts/populate_tox/populate_tox.py
index 1ca9319c2e..17fced9b4f 100644
--- a/scripts/populate_tox/populate_tox.py
+++ b/scripts/populate_tox/populate_tox.py
@@ -67,9 +67,6 @@
     "gevent",
     "opentelemetry",
     "potel",
-    # Integrations that can be migrated -- we should eventually remove all
-    # of these from the IGNORE list
-    "requests",
 }
 
 
diff --git a/scripts/populate_tox/tox.jinja b/scripts/populate_tox/tox.jinja
index 6931b64cfc..98e14adb20 100755
--- a/scripts/populate_tox/tox.jinja
+++ b/scripts/populate_tox/tox.jinja
@@ -54,9 +54,6 @@ envlist =
     # OpenTelemetry Experimental (POTel)
     {py3.8,py3.9,py3.10,py3.11,py3.12,py3.13}-potel
 
-    # Requests
-    {py3.6,py3.8,py3.12,py3.13}-requests
-
     # === Integrations - Auto-generated ===
     # These come from the populate_tox.py script. Eventually we should move all
     # integration tests there.
@@ -123,9 +120,6 @@ deps =
     # OpenTelemetry Experimental (POTel)
     potel: -e .[opentelemetry-experimental]
 
-    # Requests
-    requests: requests>=2.0
-
     # === Integrations - Auto-generated ===
     # These come from the populate_tox.py script. Eventually we should move all
     # integration tests there.
diff --git a/tox.ini b/tox.ini
index c8ec198810..662394de59 100644
--- a/tox.ini
+++ b/tox.ini
@@ -10,7 +10,7 @@
 # The file (and all resulting CI YAMLs) then need to be regenerated via
 # "scripts/generate-test-files.sh".
 #
-# Last generated: 2025-09-19T11:39:21.755227+00:00
+# Last generated: 2025-09-19T11:53:09.269997+00:00
 
 [tox]
 requires =
@@ -54,9 +54,6 @@ envlist =
     # OpenTelemetry Experimental (POTel)
     {py3.8,py3.9,py3.10,py3.11,py3.12,py3.13}-potel
 
-    # Requests
-    {py3.6,py3.8,py3.12,py3.13}-requests
-
     # === Integrations - Auto-generated ===
     # These come from the populate_tox.py script. Eventually we should move all
     # integration tests there.
@@ -194,6 +191,9 @@ envlist =
     {py3.7,py3.10,py3.11}-httpx-v0.24.1
     {py3.9,py3.11,py3.12}-httpx-v0.28.1
 
+    {py3.6}-requests-v2.12.5
+    {py3.9,py3.12,py3.13}-requests-v2.32.5
+
 
     # ~~~ Tasks ~~~
     {py3.7,py3.9,py3.10}-arq-v0.23
@@ -371,9 +371,6 @@ deps =
     # OpenTelemetry Experimental (POTel)
     potel: -e .[opentelemetry-experimental]
 
-    # Requests
-    requests: requests>=2.0
-
     # === Integrations - Auto-generated ===
     # These come from the populate_tox.py script. Eventually we should move all
     # integration tests there.
@@ -561,6 +558,9 @@ deps =
     httpx-v0.24.1: pytest-httpx==0.22.0
     httpx-v0.28.1: pytest-httpx==0.35.0
 
+    requests-v2.12.5: requests==2.12.5
+    requests-v2.32.5: requests==2.32.5
+
 
     # ~~~ Tasks ~~~
     arq-v0.23: arq==0.23