diff --git a/.chloggen/cap-urllib3-for-py38-support.yaml b/.chloggen/cap-urllib3-for-py38-support.yaml
new file mode 100755
index 0000000000..6e59b36ac6
--- /dev/null
+++ b/.chloggen/cap-urllib3-for-py38-support.yaml
@@ -0,0 +1,16 @@
+# One of 'breaking', 'deprecation', 'new_component', 'enhancement', 'bug_fix'
+change_type: 'bug_fix'
+
+# The name of the component, or a single word describing the area of concern, (e.g. collector, target allocator, auto-instrumentation, opamp, github action)
+component: auto-instrumentation
+
+# A brief description of the change. Surround your text with quotes ("") if it needs to start with a backtick (`).
+note: add upper version limit to Python dependency urllib3
+
+# One or more tracking issues related to the change
+issues: [3616]
+
+# (Optional) One or more lines of additional information to render under the primary note.
+# These lines will be padded with 2 spaces and then inserted directly into the document.
+# Use pipe (|) for multiline entries.
+subtext:
diff --git a/autoinstrumentation/python/requirements.txt b/autoinstrumentation/python/requirements.txt
index d0a0922449..76fdca2392 100644
--- a/autoinstrumentation/python/requirements.txt
+++ b/autoinstrumentation/python/requirements.txt
@@ -1,4 +1,9 @@
 opentelemetry-distro==0.51b0
+
+# We add an upper limit to urllib3 version else Python 3.8 support is dropped.
+# TODO: Update autoinstrumentation image builds to support all supported Python versions
+#       https://github.com/open-telemetry/opentelemetry-operator/issues/3712
+urllib3 < 2.3.0
 # We don't use the distro[otlp] option which automatically includes exporters since gRPC is not appropriate for
 # injected auto-instrumentation, where it has a strict dependency on the OS / Python version the artifact is built for.
 opentelemetry-exporter-otlp-proto-http==1.30.0