diff --git a/tests/e2e/configs/retry_it10_timeout_triggers_retry.yaml b/tests/e2e/configs/retry_it10_timeout_triggers_retry.yaml
new file mode 100644
index 00000000..22a340d1
--- /dev/null
+++ b/tests/e2e/configs/retry_it10_timeout_triggers_retry.yaml
@@ -0,0 +1,27 @@
+version: v0.3.0
+
+listeners:
+  - type: model
+    name: model_listener
+    port: 12000
+
+model_providers:
+  - model: openai/gpt-4o
+    base_url: http://host.docker.internal:${MOCK_PRIMARY_PORT}
+    access_key: test-key-primary
+    default: true
+    retry_policy:
+      fallback_models: [anthropic/claude-3-5-sonnet]
+      default_strategy: "different_provider"
+      default_max_attempts: 2
+      on_status_codes:
+        - codes: [429]
+          strategy: "different_provider"
+          max_attempts: 2
+      on_timeout:
+        strategy: "different_provider"
+        max_attempts: 2
+
+  - model: anthropic/claude-3-5-sonnet
+    base_url: http://host.docker.internal:${MOCK_SECONDARY_PORT}
+    access_key: test-key-secondary
diff --git a/tests/e2e/configs/retry_it11_high_latency_failover.yaml b/tests/e2e/configs/retry_it11_high_latency_failover.yaml
new file mode 100644
index 00000000..1dc8a7e2
--- /dev/null
+++ b/tests/e2e/configs/retry_it11_high_latency_failover.yaml
@@ -0,0 +1,33 @@
+version: v0.3.0
+
+listeners:
+  - type: model
+    name: model_listener
+    port: 12000
+
+model_providers:
+  - model: openai/gpt-4o
+    base_url: http://host.docker.internal:${MOCK_PRIMARY_PORT}
+    access_key: test-key-primary
+    default: true
+    retry_policy:
+      fallback_models: [anthropic/claude-3-5-sonnet]
+      default_strategy: "different_provider"
+      default_max_attempts: 2
+      on_status_codes:
+        - codes: [429]
+          strategy: "different_provider"
+          max_attempts: 2
+      on_high_latency:
+        threshold_ms: 1000
+        measure: "total"
+        min_triggers: 1
+        strategy: "different_provider"
+        max_attempts: 2
+        block_duration_seconds: 60
+        scope: "model"
+        apply_to: "global"
+
+  - model: anthropic/claude-3-5-sonnet
+    base_url: http://host.docker.internal:${MOCK_SECONDARY_PORT}
+    access_key: test-key-secondary
diff --git a/tests/e2e/configs/retry_it12_streaming.yaml b/tests/e2e/configs/retry_it12_streaming.yaml
new file mode 100644
index 00000000..f1933fa0
--- /dev/null
+++ b/tests/e2e/configs/retry_it12_streaming.yaml
@@ -0,0 +1,23 @@
+version: v0.3.0
+
+listeners:
+  - type: model
+    name: model_listener
+    port: 12000
+
+model_providers:
+  - model: openai/gpt-4o
+    base_url: http://host.docker.internal:${MOCK_PRIMARY_PORT}
+    access_key: test-key-primary
+    default: true
+    retry_policy:
+      default_strategy: "different_provider"
+      default_max_attempts: 2
+      on_status_codes:
+        - codes: [429]
+          strategy: "different_provider"
+          max_attempts: 2
+
+  - model: anthropic/claude-3-5-sonnet
+    base_url: http://host.docker.internal:${MOCK_SECONDARY_PORT}
+    access_key: test-key-secondary
diff --git a/tests/e2e/configs/retry_it13_body_preserved.yaml b/tests/e2e/configs/retry_it13_body_preserved.yaml
new file mode 100644
index 00000000..f1933fa0
--- /dev/null
+++ b/tests/e2e/configs/retry_it13_body_preserved.yaml
@@ -0,0 +1,23 @@
+version: v0.3.0
+
+listeners:
+  - type: model
+    name: model_listener
+    port: 12000
+
+model_providers:
+  - model: openai/gpt-4o
+    base_url: http://host.docker.internal:${MOCK_PRIMARY_PORT}
+    access_key: test-key-primary
+    default: true
+    retry_policy:
+      default_strategy: "different_provider"
+      default_max_attempts: 2
+      on_status_codes:
+        - codes: [429]
+          strategy: "different_provider"
+          max_attempts: 2
+
+  - model: anthropic/claude-3-5-sonnet
+    base_url: http://host.docker.internal:${MOCK_SECONDARY_PORT}
+    access_key: test-key-secondary
diff --git a/tests/e2e/configs/retry_it1_basic_429.yaml b/tests/e2e/configs/retry_it1_basic_429.yaml
new file mode 100644
index 00000000..f1933fa0
--- /dev/null
+++ b/tests/e2e/configs/retry_it1_basic_429.yaml
@@ -0,0 +1,23 @@
+version: v0.3.0
+
+listeners:
+  - type: model
+    name: model_listener
+    port: 12000
+
+model_providers:
+  - model: openai/gpt-4o
+    base_url: http://host.docker.internal:${MOCK_PRIMARY_PORT}
+    access_key: test-key-primary
+    default: true
+    retry_policy:
+      default_strategy: "different_provider"
+      default_max_attempts: 2
+      on_status_codes:
+        - codes: [429]
+          strategy: "different_provider"
+          max_attempts: 2
+
+  - model: anthropic/claude-3-5-sonnet
+    base_url: http://host.docker.internal:${MOCK_SECONDARY_PORT}
+    access_key: test-key-secondary
diff --git a/tests/e2e/configs/retry_it2_503_different_provider.yaml b/tests/e2e/configs/retry_it2_503_different_provider.yaml
new file mode 100644
index 00000000..38fe2edb
--- /dev/null
+++ b/tests/e2e/configs/retry_it2_503_different_provider.yaml
@@ -0,0 +1,23 @@
+version: v0.3.0
+
+listeners:
+  - type: model
+    name: model_listener
+    port: 12000
+
+model_providers:
+  - model: openai/gpt-4o
+    base_url: http://host.docker.internal:${MOCK_PRIMARY_PORT}
+    access_key: test-key-primary
+    default: true
+    retry_policy:
+      default_strategy: "different_provider"
+      default_max_attempts: 2
+      on_status_codes:
+        - codes: [503]
+          strategy: "different_provider"
+          max_attempts: 2
+
+  - model: anthropic/claude-3-5-sonnet
+    base_url: http://host.docker.internal:${MOCK_SECONDARY_PORT}
+    access_key: test-key-secondary
diff --git a/tests/e2e/configs/retry_it3_all_exhausted.yaml b/tests/e2e/configs/retry_it3_all_exhausted.yaml
new file mode 100644
index 00000000..f1933fa0
--- /dev/null
+++ b/tests/e2e/configs/retry_it3_all_exhausted.yaml
@@ -0,0 +1,23 @@
+version: v0.3.0
+
+listeners:
+  - type: model
+    name: model_listener
+    port: 12000
+
+model_providers:
+  - model: openai/gpt-4o
+    base_url: http://host.docker.internal:${MOCK_PRIMARY_PORT}
+    access_key: test-key-primary
+    default: true
+    retry_policy:
+      default_strategy: "different_provider"
+      default_max_attempts: 2
+      on_status_codes:
+        - codes: [429]
+          strategy: "different_provider"
+          max_attempts: 2
+
+  - model: anthropic/claude-3-5-sonnet
+    base_url: http://host.docker.internal:${MOCK_SECONDARY_PORT}
+    access_key: test-key-secondary
diff --git a/tests/e2e/configs/retry_it4_no_retry_policy.yaml b/tests/e2e/configs/retry_it4_no_retry_policy.yaml
new file mode 100644
index 00000000..26bf31a6
--- /dev/null
+++ b/tests/e2e/configs/retry_it4_no_retry_policy.yaml
@@ -0,0 +1,17 @@
+version: v0.3.0
+
+listeners:
+  - type: model
+    name: model_listener
+    port: 12000
+
+model_providers:
+  - model: openai/gpt-4o
+    base_url: http://host.docker.internal:${MOCK_PRIMARY_PORT}
+    access_key: test-key-primary
+    default: true
+    # No retry_policy — errors should be returned directly to client
+
+  - model: anthropic/claude-3-5-sonnet
+    base_url: http://host.docker.internal:${MOCK_SECONDARY_PORT}
+    access_key: test-key-secondary
diff --git a/tests/e2e/configs/retry_it5_max_attempts.yaml b/tests/e2e/configs/retry_it5_max_attempts.yaml
new file mode 100644
index 00000000..f1cfa815
--- /dev/null
+++ b/tests/e2e/configs/retry_it5_max_attempts.yaml
@@ -0,0 +1,27 @@
+version: v0.3.0
+
+listeners:
+  - type: model
+    name: model_listener
+    port: 12000
+
+model_providers:
+  - model: openai/gpt-4o
+    base_url: http://host.docker.internal:${MOCK_PRIMARY_PORT}
+    access_key: test-key-primary
+    default: true
+    retry_policy:
+      default_strategy: "different_provider"
+      default_max_attempts: 1
+      on_status_codes:
+        - codes: [429]
+          strategy: "different_provider"
+          max_attempts: 1
+
+  - model: anthropic/claude-3-5-sonnet
+    base_url: http://host.docker.internal:${MOCK_SECONDARY_PORT}
+    access_key: test-key-secondary
+
+  - model: mistral/mistral-large
+    base_url: http://host.docker.internal:${MOCK_TERTIARY_PORT}
+    access_key: test-key-tertiary
diff --git a/tests/e2e/configs/retry_it6_backoff_delay.yaml b/tests/e2e/configs/retry_it6_backoff_delay.yaml
new file mode 100644
index 00000000..e7ec474c
--- /dev/null
+++ b/tests/e2e/configs/retry_it6_backoff_delay.yaml
@@ -0,0 +1,24 @@
+version: v0.3.0
+
+listeners:
+  - type: model
+    name: model_listener
+    port: 12000
+
+model_providers:
+  - model: openai/gpt-4o
+    base_url: http://host.docker.internal:${MOCK_PRIMARY_PORT}
+    access_key: test-key-primary
+    default: true
+    retry_policy:
+      default_strategy: "same_model"
+      default_max_attempts: 3
+      on_status_codes:
+        - codes: [429]
+          strategy: "same_model"
+          max_attempts: 3
+      backoff:
+        apply_to: "same_model"
+        base_ms: 500
+        max_ms: 5000
+        jitter: false
diff --git a/tests/e2e/configs/retry_it7_fallback_priority.yaml b/tests/e2e/configs/retry_it7_fallback_priority.yaml
new file mode 100644
index 00000000..e5bee0c5
--- /dev/null
+++ b/tests/e2e/configs/retry_it7_fallback_priority.yaml
@@ -0,0 +1,28 @@
+version: v0.3.0
+
+listeners:
+  - type: model
+    name: model_listener
+    port: 12000
+
+model_providers:
+  - model: openai/gpt-4o
+    base_url: http://host.docker.internal:${MOCK_PRIMARY_PORT}
+    access_key: test-key-primary
+    default: true
+    retry_policy:
+      fallback_models: [anthropic/claude-3-5-sonnet, mistral/mistral-large]
+      default_strategy: "different_provider"
+      default_max_attempts: 3
+      on_status_codes:
+        - codes: [429]
+          strategy: "different_provider"
+          max_attempts: 3
+
+  - model: anthropic/claude-3-5-sonnet
+    base_url: http://host.docker.internal:${MOCK_FALLBACK1_PORT}
+    access_key: test-key-fallback1
+
+  - model: mistral/mistral-large
+    base_url: http://host.docker.internal:${MOCK_FALLBACK2_PORT}
+    access_key: test-key-fallback2
diff --git a/tests/e2e/configs/retry_it8_retry_after_honored.yaml b/tests/e2e/configs/retry_it8_retry_after_honored.yaml
new file mode 100644
index 00000000..3088759d
--- /dev/null
+++ b/tests/e2e/configs/retry_it8_retry_after_honored.yaml
@@ -0,0 +1,23 @@
+version: v0.3.0
+
+listeners:
+  - type: model
+    name: model_listener
+    port: 12000
+
+model_providers:
+  - model: openai/gpt-4o
+    base_url: http://host.docker.internal:${MOCK_PRIMARY_PORT}
+    access_key: test-key-primary
+    default: true
+    retry_policy:
+      default_strategy: "same_model"
+      default_max_attempts: 2
+      on_status_codes:
+        - codes: [429]
+          strategy: "same_model"
+          max_attempts: 2
+      retry_after_handling:
+        scope: "model"
+        apply_to: "request"
+        max_retry_after_seconds: 300
diff --git a/tests/e2e/configs/retry_it9_retry_after_blocks_selection.yaml b/tests/e2e/configs/retry_it9_retry_after_blocks_selection.yaml
new file mode 100644
index 00000000..ef3d7ad7
--- /dev/null
+++ b/tests/e2e/configs/retry_it9_retry_after_blocks_selection.yaml
@@ -0,0 +1,36 @@
+version: v0.3.0
+
+listeners:
+  - type: model
+    name: model_listener
+    port: 12000
+
+model_providers:
+  - model: openai/gpt-4o
+    base_url: http://host.docker.internal:${MOCK_PRIMARY_PORT}
+    access_key: test-key-primary
+    default: true
+    retry_policy:
+      fallback_models: [anthropic/claude-3-5-sonnet]
+      default_strategy: "different_provider"
+      default_max_attempts: 2
+      on_status_codes:
+        - codes: [429]
+          strategy: "different_provider"
+          max_attempts: 2
+      retry_after_handling:
+        scope: "model"
+        apply_to: "global"
+        max_retry_after_seconds: 300
+
+  - model: anthropic/claude-3-5-sonnet
+    base_url: http://host.docker.internal:${MOCK_SECONDARY_PORT}
+    access_key: test-key-secondary
+    default: false
+    retry_policy:
+      default_strategy: "different_provider"
+      default_max_attempts: 2
+      on_status_codes:
+        - codes: [429]
+          strategy: "different_provider"
+          max_attempts: 2