diff --git a/lib/datadog/di/probe_notification_builder.rb b/lib/datadog/di/probe_notification_builder.rb
index 5bdb7ad8fdb..c1d74fdd48a 100644
--- a/lib/datadog/di/probe_notification_builder.rb
+++ b/lib/datadog/di/probe_notification_builder.rb
@@ -101,12 +101,17 @@ def build_snapshot(context)
         end
 
         timestamp = timestamp_now
+        message = nil
+        evaluation_errors = []
+        if segments = probe.template_segments
+          message, evaluation_errors = evaluate_template(segments, context)
+        end
         {
           service: settings.service,
           "debugger.snapshot": {
             id: SecureRandom.uuid,
             timestamp: timestamp,
-            evaluationErrors: [],
+            evaluationErrors: evaluation_errors,
             probe: {
               id: probe.id,
               version: 0,
@@ -136,10 +141,7 @@ def build_snapshot(context)
           "dd.trace_id": active_trace&.id&.to_s,
           "dd.span_id": active_span&.id&.to_s,
           ddsource: 'dd_debugger',
-          message: probe.template_segments && evaluate_template(
-            probe.template_segments,
-            context
-          ),
+          message: message,
           #duration: duration ? duration * 1000 : 0),
           timestamp: timestamp,
         }
@@ -172,7 +174,8 @@ def format_caller_locations(caller_locations)
       end
 
       def evaluate_template(template_segments, context)
-        template_segments.map do |segment|
+        evaluation_errors = []
+        message = template_segments.map do |segment|
           case segment
           when String
             segment
@@ -181,7 +184,11 @@ def evaluate_template(template_segments, context)
           else
             raise ArgumentError, "Invalid template segment type: #{segment}"
           end
-        end.join('')
+        rescue => exc
+          evaluation_errors << "#{exc.class}: #{exc}"
+          '[evaluation error]'
+        end.join
+        [message, evaluation_errors]
       end
 
       def timestamp_now
diff --git a/sig/datadog/di/probe_notification_builder.rbs b/sig/datadog/di/probe_notification_builder.rbs
index f5fb1410b99..05f5f919a57 100644
--- a/sig/datadog/di/probe_notification_builder.rbs
+++ b/sig/datadog/di/probe_notification_builder.rbs
@@ -24,7 +24,7 @@ module Datadog
 
       def format_caller_locations: (Array[untyped] callers) -> Array[Hash[Symbol,untyped]]
 
-      def evaluate_template: (untyped template, EL::Context context) -> String
+      def evaluate_template: (untyped template, EL::Context context) -> [String, Array[String]]
 
       def timestamp_now: () -> Integer
 
diff --git a/spec/datadog/di/integration/probe_notification_builder_spec.rb b/spec/datadog/di/integration/probe_notification_builder_spec.rb
index 948b06c2b22..8f55fdcd5be 100644
--- a/spec/datadog/di/integration/probe_notification_builder_spec.rb
+++ b/spec/datadog/di/integration/probe_notification_builder_spec.rb
@@ -135,10 +135,14 @@
           {id: '11', name: 'bar', type: 'LOG_PROBE', where: {
                                                        typeName: 'Foo', methodName: 'bar'
                                                      },
-           segments: [
-             {str: 'hello'},
-             {json: {ref: 'bar'}},
-           ],}
+           segments: segments}
+        end
+
+        let(:segments) do
+          [
+            {str: 'hello'},
+            {json: {ref: 'bar'}},
+          ]
         end
 
         let(:probe) do
@@ -165,6 +169,49 @@
           expect(payload.fetch(:"debugger.snapshot").fetch(:captures)).to be nil
         end
 
+        context 'when there is an evaluation error' do
+          let(:segments) do
+            [
+              {str: 'hello'},
+              {json: {substring: ['bar', 'baz', 3]}},
+            ]
+          end
+
+          it 'replaces bogus expressions with [evaluation error] and fills out evaluation errors' do
+            payload = builder.build_snapshot(context)
+            expect(payload).to be_a(Hash)
+            expect(payload[:message]).to eq "hello[evaluation error]"
+            expect(payload[:"debugger.snapshot"][:evaluationErrors]).to eq ['ArgumentError: bad value for range']
+
+            # We asked to not create a snapshot
+            expect(payload.fetch(:"debugger.snapshot").fetch(:captures)).to be nil
+          end
+        end
+
+        context 'when there are multiple evaluation errors' do
+          let(:segments) do
+            [
+              {str: 'hello'},
+              {json: {substring: ['bar', 'baz', 3]}},
+              {json: {filter: ['bar', 'baz']}},
+              {str: 'hello'},
+            ]
+          end
+
+          it 'attempts to evaluate all expressions' do
+            payload = builder.build_snapshot(context)
+            expect(payload).to be_a(Hash)
+            expect(payload[:message]).to eq "hello[evaluation error][evaluation error]hello"
+            expect(payload[:"debugger.snapshot"][:evaluationErrors]).to eq [
+              'ArgumentError: bad value for range',
+              'Datadog::DI::Error::ExpressionEvaluationError: Bad collection type for filter: String',
+            ]
+
+            # We asked to not create a snapshot
+            expect(payload.fetch(:"debugger.snapshot").fetch(:captures)).to be nil
+          end
+        end
+
         context 'when variables are referenced but none are passed in' do
           let(:context) do
             Datadog::DI::EL::Context.new(
diff --git a/spec/datadog/di/probe_notification_builder_spec.rb b/spec/datadog/di/probe_notification_builder_spec.rb
index 8e8ff8b4937..ef4320c4a21 100644
--- a/spec/datadog/di/probe_notification_builder_spec.rb
+++ b/spec/datadog/di/probe_notification_builder_spec.rb
@@ -371,7 +371,7 @@
       let(:expected) { %(test "'\\\\a\#{value}) }
 
       it 'substitutes correctly' do
-        expect(builder.send(:evaluate_template, template_segments, context)).to eq(expected)
+        expect(builder.send(:evaluate_template, template_segments, context)).to eq([expected, []])
       end
     end
   end