diff --git a/config.example.yaml b/config.example.yaml
index 7c0a5180b..f4e771470 100644
--- a/config.example.yaml
+++ b/config.example.yaml
@@ -312,6 +312,9 @@ nonstream-keepalive-interval: 0
 #     base-url: "https://generativelanguage.googleapis.com"
 #     headers:
 #       X-Custom-Header: "custom-value"
+#       # Values starting with "$" dynamically copy the header value from downstream client requests.
+#       # If the client did not send the specified header, the header is omitted.
+#       # X-Claude-Code-Session-Id: "$ABC" # copies client's "ABC" header
 #     proxy-url: "socks5://proxy.example.com:1080"
 #     # proxy-url: "direct" # optional: explicit direct connect for this credential
 #     models:
@@ -346,6 +349,9 @@ nonstream-keepalive-interval: 0
 #     base-url: "https://generativelanguage.googleapis.com"
 #     headers:
 #       X-Custom-Header: "custom-value"
+#       # Values starting with "$" dynamically copy the header value from downstream client requests.
+#       # If the client did not send the specified header, the header is omitted.
+#       # X-Claude-Code-Session-Id: "$ABC" # copies client's "ABC" header
 #     proxy-url: "socks5://proxy.example.com:1080"
 #     # proxy-url: "direct" # optional: explicit direct connect for this credential
 #     models:
@@ -374,6 +380,9 @@ nonstream-keepalive-interval: 0
 #     alpha-search: false # optional: allow this key to serve /v1/alpha/search via base-url + /alpha/search
 #     headers:
 #       X-Custom-Header: "custom-value"
+#       # Values starting with "$" dynamically copy the header value from downstream client requests.
+#       # If the client did not send the specified header, the header is omitted.
+#       # X-Claude-Code-Session-Id: "$ABC" # copies client's "ABC" header
 #     proxy-url: "socks5://proxy.example.com:1080" # optional: per-key proxy override
 #     # proxy-url: "direct" # optional: explicit direct connect for this credential
 #     models:
@@ -413,6 +422,9 @@ nonstream-keepalive-interval: 0
 #     websockets: true # optional: use the xAI upstream websocket transport for downstream websocket requests
 #     headers:
 #       X-Custom-Header: "custom-value"
+#       # Values starting with "$" dynamically copy the header value from downstream client requests.
+#       # If the client did not send the specified header, the header is omitted.
+#       # X-Claude-Code-Session-Id: "$ABC" # copies client's "ABC" header
 #     proxy-url: "socks5://proxy.example.com:1080" # optional: per-key proxy override
 #     # proxy-url: "direct" # optional: explicit direct connect for this credential
 #     models:
@@ -444,6 +456,9 @@ nonstream-keepalive-interval: 0
 #     base-url: "https://www.example.com" # use the custom claude API endpoint
 #     headers:
 #       X-Custom-Header: "custom-value"
+#       # Values starting with "$" dynamically copy the header value from downstream client requests.
+#       # If the client did not send the specified header, the header is omitted.
+#       # X-Claude-Code-Session-Id: "$ABC" # copies client's "ABC" header
 #     proxy-url: "socks5://proxy.example.com:1080" # optional: per-key proxy override
 #     # proxy-url: "direct" # optional: explicit direct connect for this credential
 #     models:
@@ -589,6 +604,9 @@ nonstream-keepalive-interval: 0
 #         action: "stop" # "stop", "stop-and-cooldown", "continue", "continue-and-cooldown"
 #     headers:
 #       X-Custom-Header: "custom-value"
+#       # Values starting with "$" dynamically copy the header value from downstream client requests.
+#       # If the client did not send the specified header, the header is omitted.
+#       # X-Claude-Code-Session-Id: "$ABC" # copies client's "ABC" header
 #     api-key-entries:
 #       - api-key: "sk-or-v1-...b780"
 #         weight: 5 # optional: weighted-round-robin share; omitted defaults to 1; maximum 1,000,000
@@ -630,6 +648,9 @@ nonstream-keepalive-interval: 0
 #     # proxy-url: "direct" # optional: explicit direct connect for this credential
 #     headers:
 #       X-Custom-Header: "custom-value"
+#       # Values starting with "$" dynamically copy the header value from downstream client requests.
+#       # If the client did not send the specified header, the header is omitted.
+#       # X-Claude-Code-Session-Id: "$ABC" # copies client's "ABC" header
 #     models:                                     # optional: map aliases to upstream model names
 #       - name: "gemini-2.5-flash"                # upstream model name
 #         alias: "vertex-flash"                   # client-visible alias
diff --git a/internal/runtime/executor/claude_executor_request.go b/internal/runtime/executor/claude_executor_request.go
index 17ddc80e6..39e0f4ad9 100644
--- a/internal/runtime/executor/claude_executor_request.go
+++ b/internal/runtime/executor/claude_executor_request.go
@@ -927,7 +927,7 @@ func applyClaudeHeadersWithNativeProfile(
 	if auth != nil {
 		attrs = auth.Attributes
 	}
-	util.ApplyCustomHeadersFromAttrs(r, attrs)
+	util.ApplyCustomHeadersFromAttrs(r, attrs, incomingHeaders)
 	// Custom credential headers are a configuration escape hatch for third-party
 	// gateways, so they keep the last word there. On api.anthropic.com they must
 	// not rewrite the reconstructed identity: an overridden Anthropic-Beta yields a
diff --git a/internal/runtime/executor/codex_executor_execute.go b/internal/runtime/executor/codex_executor_execute.go
index 5d774908c..d7c6dbd7f 100644
--- a/internal/runtime/executor/codex_executor_execute.go
+++ b/internal/runtime/executor/codex_executor_execute.go
@@ -79,7 +79,7 @@ func (e *CodexExecutor) Execute(ctx context.Context, auth *cliproxyauth.Auth, re
 	if err != nil {
 		return resp, err
 	}
-	applyCodexHeaders(httpReq, auth, apiKey, true, e.cfg)
+	applyCodexHeaders(httpReq, auth, apiKey, true, e.cfg, opts.Headers)
 	applyModelHeaderOverrides(httpReq.Header, baseModel)
 	applyCodexIdentityConfuseHeaders(httpReq.Header, &identityState)
 	var authID, authLabel, authType, authValue string
@@ -239,7 +239,7 @@ func (e *CodexExecutor) executeCompact(ctx context.Context, auth *cliproxyauth.A
 	if err != nil {
 		return resp, err
 	}
-	applyCodexHeaders(httpReq, auth, apiKey, false, e.cfg)
+	applyCodexHeaders(httpReq, auth, apiKey, false, e.cfg, opts.Headers)
 	applyModelHeaderOverrides(httpReq.Header, baseModel)
 	applyCodexIdentityConfuseHeaders(httpReq.Header, &identityState)
 	var authID, authLabel, authType, authValue string
diff --git a/internal/runtime/executor/codex_executor_request.go b/internal/runtime/executor/codex_executor_request.go
index ea65cafc6..205a40235 100644
--- a/internal/runtime/executor/codex_executor_request.go
+++ b/internal/runtime/executor/codex_executor_request.go
@@ -276,9 +276,11 @@ func codexIdentityConfuseUUID(authID string, kind string, value string) string {
 	return uuid.NewSHA1(uuid.NameSpaceOID, []byte(name)).String()
 }
 
-func applyCodexHeaders(r *http.Request, auth *cliproxyauth.Auth, token string, stream bool, cfg *config.Config) {
+func applyCodexHeaders(r *http.Request, auth *cliproxyauth.Auth, token string, stream bool, cfg *config.Config, clientHeaders ...http.Header) {
 	var ginHeaders http.Header
-	if ginCtx, ok := r.Context().Value("gin").(*gin.Context); ok && ginCtx != nil && ginCtx.Request != nil {
+	if len(clientHeaders) > 0 && clientHeaders[0] != nil {
+		ginHeaders = clientHeaders[0]
+	} else if ginCtx, ok := r.Context().Value("gin").(*gin.Context); ok && ginCtx != nil && ginCtx.Request != nil {
 		ginHeaders = ginCtx.Request.Header
 	}
 	applyCodexHeadersFromSources(r, auth, token, stream, cfg, ginHeaders)
@@ -303,9 +305,12 @@ func applyModelHeaderOverrides(headers http.Header, modelName string) {
 
 // applyCodexDirectImageHeaders sets Codex upstream headers for direct /images/* calls.
 // Downstream client User-Agent values are not forwarded to reduce Cloudflare 1010 blocks.
-func applyCodexDirectImageHeaders(r *http.Request, auth *cliproxyauth.Auth, token string, stream bool, cfg *config.Config) {
+func applyCodexDirectImageHeaders(r *http.Request, auth *cliproxyauth.Auth, token string, stream bool, cfg *config.Config, clientHeaders ...http.Header) {
 	var ginHeaders http.Header
-	if ginCtx, ok := r.Context().Value("gin").(*gin.Context); ok && ginCtx != nil && ginCtx.Request != nil {
+	if len(clientHeaders) > 0 && clientHeaders[0] != nil {
+		ginHeaders = clientHeaders[0].Clone()
+		ginHeaders.Del("User-Agent")
+	} else if ginCtx, ok := r.Context().Value("gin").(*gin.Context); ok && ginCtx != nil && ginCtx.Request != nil {
 		ginHeaders = ginCtx.Request.Header.Clone()
 		ginHeaders.Del("User-Agent")
 	}
@@ -359,7 +364,7 @@ func applyCodexHeadersFromSources(r *http.Request, auth *cliproxyauth.Auth, toke
 	if auth != nil {
 		attrs = auth.Attributes
 	}
-	util.ApplyCustomHeadersFromAttrs(r, attrs)
+	util.ApplyCustomHeadersFromAttrs(r, attrs, ginHeaders)
 	applyCodexCloakingHeaders(r.Header, cfg)
 }
 
diff --git a/internal/runtime/executor/codex_executor_stream.go b/internal/runtime/executor/codex_executor_stream.go
index d6e622646..00dc46ad4 100644
--- a/internal/runtime/executor/codex_executor_stream.go
+++ b/internal/runtime/executor/codex_executor_stream.go
@@ -83,7 +83,7 @@ func (e *CodexExecutor) ExecuteStream(ctx context.Context, auth *cliproxyauth.Au
 	if err != nil {
 		return nil, err
 	}
-	applyCodexHeaders(httpReq, auth, apiKey, true, e.cfg)
+	applyCodexHeaders(httpReq, auth, apiKey, true, e.cfg, opts.Headers)
 	applyModelHeaderOverrides(httpReq.Header, baseModel)
 	applyCodexIdentityConfuseHeaders(httpReq.Header, &identityState)
 	var authID, authLabel, authType, authValue string
diff --git a/internal/runtime/executor/codex_openai_images.go b/internal/runtime/executor/codex_openai_images.go
index 18ef44186..5492f37ef 100644
--- a/internal/runtime/executor/codex_openai_images.go
+++ b/internal/runtime/executor/codex_openai_images.go
@@ -112,7 +112,7 @@ func (e *CodexExecutor) executeOpenAIImage(ctx context.Context, auth *cliproxyau
 	if errCache != nil {
 		return resp, errCache
 	}
-	applyCodexHeaders(httpReq, auth, apiKey, true, e.cfg)
+	applyCodexHeaders(httpReq, auth, apiKey, true, e.cfg, opts.Headers)
 	applyModelHeaderOverrides(httpReq.Header, mainModel)
 	applyCodexIdentityConfuseHeaders(httpReq.Header, &identityState)
 	recordCodexOpenAIImageRequest(ctx, e.cfg, e.Identifier(), auth, url, httpReq.Header.Clone(), body)
@@ -209,7 +209,7 @@ func (e *CodexExecutor) executeOpenAIImageStream(ctx context.Context, auth *clip
 	if errCache != nil {
 		return nil, errCache
 	}
-	applyCodexHeaders(httpReq, auth, apiKey, true, e.cfg)
+	applyCodexHeaders(httpReq, auth, apiKey, true, e.cfg, opts.Headers)
 	applyModelHeaderOverrides(httpReq.Header, mainModel)
 	applyCodexIdentityConfuseHeaders(httpReq.Header, &identityState)
 	recordCodexOpenAIImageRequest(ctx, e.cfg, e.Identifier(), auth, url, httpReq.Header.Clone(), body)
diff --git a/internal/runtime/executor/codex_websockets_execute.go b/internal/runtime/executor/codex_websockets_execute.go
index 136c51273..72bace8cf 100644
--- a/internal/runtime/executor/codex_websockets_execute.go
+++ b/internal/runtime/executor/codex_websockets_execute.go
@@ -85,7 +85,7 @@ func (e *CodexWebsocketsExecutor) Execute(ctx context.Context, auth *cliproxyaut
 	var identityState codexIdentityConfuseState
 	upstreamBody, identityState := applyCodexIdentityConfuseBody(e.cfg, auth, originalPayloadSource, body)
 	reporter.SetTranslatedReasoningEffort(clientBody, to.String())
-	wsHeaders = applyCodexWebsocketHeaders(ctx, wsHeaders, auth, apiKey, e.cfg)
+	wsHeaders = applyCodexWebsocketHeaders(ctx, wsHeaders, auth, apiKey, e.cfg, opts.Headers)
 	applyModelHeaderOverrides(wsHeaders, baseModel)
 	applyCodexIdentityConfuseHeaders(wsHeaders, &identityState)
 
diff --git a/internal/runtime/executor/codex_websockets_request.go b/internal/runtime/executor/codex_websockets_request.go
index 7d1cf92dd..977102fe1 100644
--- a/internal/runtime/executor/codex_websockets_request.go
+++ b/internal/runtime/executor/codex_websockets_request.go
@@ -64,7 +64,7 @@ func applyCodexPromptCacheHeadersWithContext(ctx context.Context, from sdktransl
 	return rawJSON, headers, nil
 }
 
-func applyCodexWebsocketHeaders(ctx context.Context, headers http.Header, auth *cliproxyauth.Auth, token string, cfg *config.Config) http.Header {
+func applyCodexWebsocketHeaders(ctx context.Context, headers http.Header, auth *cliproxyauth.Auth, token string, cfg *config.Config, clientHeaders ...http.Header) http.Header {
 	if headers == nil {
 		headers = http.Header{}
 	}
@@ -73,7 +73,9 @@ func applyCodexWebsocketHeaders(ctx context.Context, headers http.Header, auth *
 	}
 
 	var ginHeaders http.Header
-	if ginCtx, ok := ctx.Value("gin").(*gin.Context); ok && ginCtx != nil && ginCtx.Request != nil {
+	if len(clientHeaders) > 0 && clientHeaders[0] != nil {
+		ginHeaders = clientHeaders[0].Clone()
+	} else if ginCtx, ok := ctx.Value("gin").(*gin.Context); ok && ginCtx != nil && ginCtx.Request != nil {
 		ginHeaders = ginCtx.Request.Header.Clone()
 	}
 
@@ -123,7 +125,7 @@ func applyCodexWebsocketHeaders(ctx context.Context, headers http.Header, auth *
 	if auth != nil {
 		attrs = auth.Attributes
 	}
-	util.ApplyCustomHeadersFromAttrs(&http.Request{Header: headers}, attrs)
+	util.ApplyCustomHeadersFromAttrs(&http.Request{Header: headers}, attrs, ginHeaders)
 	applyCodexCloakingHeaders(headers, cfg)
 
 	return headers
diff --git a/internal/runtime/executor/codex_websockets_stream.go b/internal/runtime/executor/codex_websockets_stream.go
index 1aec1c3f9..d094a894b 100644
--- a/internal/runtime/executor/codex_websockets_stream.go
+++ b/internal/runtime/executor/codex_websockets_stream.go
@@ -82,7 +82,7 @@ func (e *CodexWebsocketsExecutor) ExecuteStream(ctx context.Context, auth *clipr
 	var identityState codexIdentityConfuseState
 	upstreamBody, identityState := applyCodexIdentityConfuseBody(e.cfg, auth, originalPayloadSource, body)
 	reporter.SetTranslatedReasoningEffort(clientBody, to.String())
-	wsHeaders = applyCodexWebsocketHeaders(ctx, wsHeaders, auth, apiKey, e.cfg)
+	wsHeaders = applyCodexWebsocketHeaders(ctx, wsHeaders, auth, apiKey, e.cfg, opts.Headers)
 	applyModelHeaderOverrides(wsHeaders, baseModel)
 	applyCodexIdentityConfuseHeaders(wsHeaders, &identityState)
 
diff --git a/internal/runtime/executor/custom_magic_headers_test.go b/internal/runtime/executor/custom_magic_headers_test.go
new file mode 100644
index 000000000..5fc0ad86c
--- /dev/null
+++ b/internal/runtime/executor/custom_magic_headers_test.go
@@ -0,0 +1,408 @@
+package executor
+
+import (
+	"context"
+	"io"
+	"net/http"
+	"net/http/httptest"
+	"testing"
+
+	"github.com/router-for-me/CLIProxyAPI/v7/internal/config"
+	cliproxyauth "github.com/router-for-me/CLIProxyAPI/v7/sdk/cliproxy/auth"
+	cliproxyexecutor "github.com/router-for-me/CLIProxyAPI/v7/sdk/cliproxy/executor"
+	sdktranslator "github.com/router-for-me/CLIProxyAPI/v7/sdk/translator"
+)
+
+func TestCustomMagicHeaders_OpenAICompat(t *testing.T) {
+	var gotHeaders http.Header
+	server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		gotHeaders = r.Header.Clone()
+		w.Header().Set("Content-Type", "application/json")
+		_, _ = w.Write([]byte(`{"id":"chatcmpl-1","choices":[{"message":{"role":"assistant","content":"ok"}}]}`))
+	}))
+	defer server.Close()
+
+	executor := NewOpenAICompatExecutor("openai-compatibility", &config.Config{
+		OpenAICompatibility: []config.OpenAICompatibility{{
+			Name: "compat",
+		}},
+	})
+	auth := &cliproxyauth.Auth{
+		Provider: "openai-compatibility",
+		Attributes: map[string]string{
+			"base_url":                        server.URL,
+			"api_key":                         "test-key",
+			"header:X-Claude-Code-Session-Id": "$ABC",
+			"header:X-Forwarded-Session":      "$X-Client-Session",
+			"header:X-Missing":                "$NONEXISTENT",
+			"header:X-Static":                 "static-value",
+		},
+	}
+
+	req := cliproxyexecutor.Request{
+		Model:   "gpt-4o",
+		Payload: []byte(`{"messages":[{"role":"user","content":"hi"}]}`),
+	}
+	opts := cliproxyexecutor.Options{
+		SourceFormat: sdktranslator.FormatOpenAI,
+		Headers: http.Header{
+			"Abc":              []string{"session-abc-value"},
+			"X-Client-Session": []string{"client-session-uuid-123"},
+		},
+	}
+
+	_, err := executor.Execute(context.Background(), auth, req, opts)
+	if err != nil {
+		t.Fatalf("Execute() error = %v", err)
+	}
+
+	if got := gotHeaders.Get("X-Claude-Code-Session-Id"); got != "session-abc-value" {
+		t.Errorf("X-Claude-Code-Session-Id = %q, want %q", got, "session-abc-value")
+	}
+	if got := gotHeaders.Get("X-Forwarded-Session"); got != "client-session-uuid-123" {
+		t.Errorf("X-Forwarded-Session = %q, want %q", got, "client-session-uuid-123")
+	}
+	if got := gotHeaders.Get("X-Static"); got != "static-value" {
+		t.Errorf("X-Static = %q, want %q", got, "static-value")
+	}
+	if _, exists := gotHeaders["X-Missing"]; exists {
+		t.Errorf("expected X-Missing to be omitted, got %q", gotHeaders.Get("X-Missing"))
+	}
+}
+
+func TestCustomMagicHeaders_Gemini(t *testing.T) {
+	var gotHeaders http.Header
+	server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		gotHeaders = r.Header.Clone()
+		w.Header().Set("Content-Type", "application/json")
+		_, _ = w.Write([]byte(`{"candidates":[{"content":{"parts":[{"text":"hello"}]}}]}`))
+	}))
+	defer server.Close()
+
+	executor := NewGeminiExecutor(&config.Config{})
+	auth := &cliproxyauth.Auth{
+		Provider: "gemini",
+		Attributes: map[string]string{
+			"base_url":                        server.URL,
+			"api_key":                         "gemini-key",
+			"header:X-Claude-Code-Session-Id": "$ABC",
+			"header:X-Missing":                "$NONEXISTENT",
+			"header:X-Static":                 "gemini-static",
+		},
+	}
+
+	req := cliproxyexecutor.Request{
+		Model:   "gemini-2.5-flash",
+		Payload: []byte(`{"contents":[{"parts":[{"text":"hi"}]}]}`),
+	}
+	opts := cliproxyexecutor.Options{
+		SourceFormat: sdktranslator.FormatGemini,
+		Headers: http.Header{
+			"Abc": []string{"gemini-session-abc"},
+		},
+	}
+
+	_, err := executor.Execute(context.Background(), auth, req, opts)
+	if err != nil {
+		t.Fatalf("Execute() error = %v", err)
+	}
+
+	if got := gotHeaders.Get("X-Claude-Code-Session-Id"); got != "gemini-session-abc" {
+		t.Errorf("X-Claude-Code-Session-Id = %q, want %q", got, "gemini-session-abc")
+	}
+	if got := gotHeaders.Get("X-Static"); got != "gemini-static" {
+		t.Errorf("X-Static = %q, want %q", got, "gemini-static")
+	}
+	if _, exists := gotHeaders["X-Missing"]; exists {
+		t.Errorf("expected X-Missing to be omitted, got %q", gotHeaders.Get("X-Missing"))
+	}
+}
+
+func TestCustomMagicHeaders_GeminiInteractions(t *testing.T) {
+	var gotHeaders http.Header
+	server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		gotHeaders = r.Header.Clone()
+		w.Header().Set("Content-Type", "application/json")
+		_, _ = w.Write([]byte(`{"id":"interaction_1","status":"completed","outputs":[{"text":"ok"}]}`))
+	}))
+	defer server.Close()
+
+	executor := NewGeminiExecutor(&config.Config{})
+	auth := &cliproxyauth.Auth{
+		Provider: "gemini-interactions",
+		Attributes: map[string]string{
+			"base_url":                        server.URL,
+			"api_key":                         "interactions-key",
+			"header:X-Claude-Code-Session-Id": "$ABC",
+			"header:X-Missing":                "$NONEXISTENT",
+			"header:X-Static":                 "interactions-static",
+		},
+	}
+
+	req := cliproxyexecutor.Request{
+		Model:   "gemini-3.1-flash-lite",
+		Payload: []byte(`{"messages":[{"role":"user","content":"hi"}]}`),
+	}
+	opts := cliproxyexecutor.Options{
+		SourceFormat: sdktranslator.FormatOpenAI,
+		Headers: http.Header{
+			"Abc": []string{"interactions-session-123"},
+		},
+	}
+
+	_, err := executor.Execute(context.Background(), auth, req, opts)
+	if err != nil {
+		t.Fatalf("Execute() error = %v", err)
+	}
+
+	if got := gotHeaders.Get("X-Claude-Code-Session-Id"); got != "interactions-session-123" {
+		t.Errorf("X-Claude-Code-Session-Id = %q, want %q", got, "interactions-session-123")
+	}
+	if got := gotHeaders.Get("X-Static"); got != "interactions-static" {
+		t.Errorf("X-Static = %q, want %q", got, "interactions-static")
+	}
+	if _, exists := gotHeaders["X-Missing"]; exists {
+		t.Errorf("expected X-Missing to be omitted, got %q", gotHeaders.Get("X-Missing"))
+	}
+}
+
+func TestCustomMagicHeaders_GeminiVertex(t *testing.T) {
+	var gotHeaders http.Header
+	server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		gotHeaders = r.Header.Clone()
+		w.Header().Set("Content-Type", "application/json")
+		_, _ = w.Write([]byte(`{"candidates":[{"content":{"parts":[{"text":"vertex-response"}]}}]}`))
+	}))
+	defer server.Close()
+
+	executor := NewGeminiVertexExecutor(&config.Config{})
+	auth := &cliproxyauth.Auth{
+		Provider: "vertex",
+		Attributes: map[string]string{
+			"base_url":                        server.URL,
+			"api_key":                         "vertex-api-key",
+			"header:X-Claude-Code-Session-Id": "$ABC",
+			"header:X-Missing":                "$NONEXISTENT",
+		},
+	}
+
+	req := cliproxyexecutor.Request{
+		Model:   "gemini-2.5-flash",
+		Payload: []byte(`{"contents":[{"parts":[{"text":"hi"}]}]}`),
+	}
+	opts := cliproxyexecutor.Options{
+		SourceFormat: sdktranslator.FormatGemini,
+		Headers: http.Header{
+			"Abc": []string{"vertex-session-123"},
+		},
+	}
+
+	_, err := executor.Execute(context.Background(), auth, req, opts)
+	if err != nil {
+		t.Fatalf("Execute() error = %v", err)
+	}
+
+	if got := gotHeaders.Get("X-Claude-Code-Session-Id"); got != "vertex-session-123" {
+		t.Errorf("X-Claude-Code-Session-Id = %q, want %q", got, "vertex-session-123")
+	}
+	if _, exists := gotHeaders["X-Missing"]; exists {
+		t.Errorf("expected X-Missing to be omitted, got %q", gotHeaders.Get("X-Missing"))
+	}
+}
+
+func TestCustomMagicHeaders_XAI(t *testing.T) {
+	var gotHeaders http.Header
+	server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		gotHeaders = r.Header.Clone()
+		w.Header().Set("Content-Type", "text/event-stream")
+		_, _ = w.Write([]byte("data: {\"type\":\"response.completed\",\"response\":{\"id\":\"resp_1\",\"object\":\"response\",\"created_at\":0,\"status\":\"completed\",\"background\":false,\"error\":null,\"output\":[]}}\n\n"))
+	}))
+	defer server.Close()
+
+	executor := NewXAIExecutor(&config.Config{})
+	auth := &cliproxyauth.Auth{
+		Provider: "xai",
+		Attributes: map[string]string{
+			"base_url":                        server.URL,
+			"api_key":                         "xai-key",
+			"header:X-Claude-Code-Session-Id": "$ABC",
+			"header:X-Missing":                "$NONEXISTENT",
+		},
+	}
+
+	req := cliproxyexecutor.Request{
+		Model:   "grok-2",
+		Payload: []byte(`{"messages":[{"role":"user","content":"hi"}]}`),
+	}
+	opts := cliproxyexecutor.Options{
+		SourceFormat: sdktranslator.FormatOpenAI,
+		Headers: http.Header{
+			"ABC": []string{"xai-session-value"},
+		},
+	}
+
+	_, err := executor.Execute(context.Background(), auth, req, opts)
+	if err != nil {
+		t.Fatalf("Execute() error = %v", err)
+	}
+
+	if got := gotHeaders.Get("X-Claude-Code-Session-Id"); got != "xai-session-value" {
+		t.Errorf("X-Claude-Code-Session-Id = %q, want %q", got, "xai-session-value")
+	}
+	if _, exists := gotHeaders["X-Missing"]; exists {
+		t.Errorf("expected X-Missing to be omitted, got %q", gotHeaders.Get("X-Missing"))
+	}
+}
+
+func TestCustomMagicHeaders_Claude(t *testing.T) {
+	var gotHeaders http.Header
+	server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		gotHeaders = r.Header.Clone()
+		w.Header().Set("Content-Type", "application/json")
+		_, _ = w.Write([]byte(`{"id":"msg_1","type":"message","role":"assistant","content":[{"type":"text","text":"hi"}]}`))
+	}))
+	defer server.Close()
+
+	executor := NewClaudeExecutor(&config.Config{})
+	auth := &cliproxyauth.Auth{
+		Provider: "claude",
+		Attributes: map[string]string{
+			"base_url":                        server.URL,
+			"api_key":                         "sk-ant-test",
+			"header:X-Claude-Code-Session-Id": "$ABC",
+			"header:X-Missing":                "$NONEXISTENT",
+		},
+	}
+
+	req := cliproxyexecutor.Request{
+		Model:   "claude-3-7-sonnet-20250219",
+		Payload: []byte(`{"messages":[{"role":"user","content":"hi"}]}`),
+	}
+	opts := cliproxyexecutor.Options{
+		SourceFormat: sdktranslator.FormatClaude,
+		Headers: http.Header{
+			"Abc": []string{"claude-session-value"},
+		},
+	}
+
+	_, err := executor.Execute(context.Background(), auth, req, opts)
+	if err != nil {
+		t.Fatalf("Execute() error = %v", err)
+	}
+
+	if got := gotHeaders.Get("X-Claude-Code-Session-Id"); got != "claude-session-value" {
+		t.Errorf("X-Claude-Code-Session-Id = %q, want %q", got, "claude-session-value")
+	}
+	if _, exists := gotHeaders["X-Missing"]; exists {
+		t.Errorf("expected X-Missing to be omitted, got %q", gotHeaders.Get("X-Missing"))
+	}
+}
+
+func TestCustomMagicHeaders_OpenAICompat_Stream(t *testing.T) {
+	var gotHeaders http.Header
+	server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		gotHeaders = r.Header.Clone()
+		w.Header().Set("Content-Type", "text/event-stream")
+		_, _ = w.Write([]byte("data: {\"choices\":[{\"delta\":{\"content\":\"hi\"}}]}\n\ndata: [DONE]\n\n"))
+	}))
+	defer server.Close()
+
+	executor := NewOpenAICompatExecutor("openai-compatibility", &config.Config{
+		OpenAICompatibility: []config.OpenAICompatibility{{
+			Name: "compat",
+		}},
+	})
+	auth := &cliproxyauth.Auth{
+		Provider: "openai-compatibility",
+		Attributes: map[string]string{
+			"base_url":                        server.URL,
+			"api_key":                         "test-key",
+			"header:X-Claude-Code-Session-Id": "$ABC",
+			"header:X-Empty-Var":              "$   ",
+			"header:X-Only-Dollar":            "$",
+			"header:X-Missing":                "$NONEXISTENT",
+		},
+	}
+
+	req := cliproxyexecutor.Request{
+		Model:   "gpt-4o",
+		Payload: []byte(`{"messages":[{"role":"user","content":"hi"}]}`),
+	}
+	opts := cliproxyexecutor.Options{
+		SourceFormat: sdktranslator.FormatOpenAI,
+		Stream:       true,
+		Headers: http.Header{
+			"Abc": []string{"stream-session-abc"},
+		},
+	}
+
+	result, err := executor.ExecuteStream(context.Background(), auth, req, opts)
+	if err != nil {
+		t.Fatalf("ExecuteStream() error = %v", err)
+	}
+	for range result.Chunks {
+	}
+
+	if got := gotHeaders.Get("X-Claude-Code-Session-Id"); got != "stream-session-abc" {
+		t.Errorf("X-Claude-Code-Session-Id = %q, want %q", got, "stream-session-abc")
+	}
+	if _, exists := gotHeaders["X-Missing"]; exists {
+		t.Errorf("expected X-Missing to be omitted, got %q", gotHeaders.Get("X-Missing"))
+	}
+	if _, exists := gotHeaders["X-Empty-Var"]; exists {
+		t.Errorf("expected X-Empty-Var to be omitted, got %q", gotHeaders.Get("X-Empty-Var"))
+	}
+	if _, exists := gotHeaders["X-Only-Dollar"]; exists {
+		t.Errorf("expected X-Only-Dollar to be omitted, got %q", gotHeaders.Get("X-Only-Dollar"))
+	}
+}
+
+func TestCustomMagicHeaders_Codex(t *testing.T) {
+	var gotHeaders http.Header
+	server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		gotHeaders = r.Header.Clone()
+		body, _ := io.ReadAll(r.Body)
+		_ = body
+		w.Header().Set("Content-Type", "text/event-stream")
+		_, _ = w.Write([]byte("data: {\"type\":\"response.completed\",\"response\":{\"id\":\"resp_1\",\"object\":\"response\",\"created_at\":0,\"status\":\"completed\",\"background\":false,\"error\":null,\"output\":[]}}\n\n"))
+	}))
+	defer server.Close()
+
+	executor := NewCodexExecutor(&config.Config{
+		Codex: config.CodexConfig{
+			DisableCodexCloaking: true,
+		},
+	})
+	auth := &cliproxyauth.Auth{
+		Provider: "codex",
+		Attributes: map[string]string{
+			"base_url":                        server.URL,
+			"api_key":                         "codex-key",
+			"header:X-Claude-Code-Session-Id": "$ABC",
+			"header:X-Missing":                "$NONEXISTENT",
+		},
+	}
+
+	req := cliproxyexecutor.Request{
+		Model:   "gpt-5-codex",
+		Payload: []byte(`{"messages":[{"role":"user","content":"hi"}]}`),
+	}
+	opts := cliproxyexecutor.Options{
+		SourceFormat: sdktranslator.FormatCodex,
+		Headers: http.Header{
+			"Abc": []string{"codex-session-value"},
+		},
+	}
+
+	_, err := executor.Execute(context.Background(), auth, req, opts)
+	if err != nil {
+		t.Fatalf("Execute() error = %v", err)
+	}
+
+	if got := gotHeaders.Get("X-Claude-Code-Session-Id"); got != "codex-session-value" {
+		t.Errorf("X-Claude-Code-Session-Id = %q, want %q", got, "codex-session-value")
+	}
+	if _, exists := gotHeaders["X-Missing"]; exists {
+		t.Errorf("expected X-Missing to be omitted, got %q", gotHeaders.Get("X-Missing"))
+	}
+}
diff --git a/internal/runtime/executor/gemini_executor.go b/internal/runtime/executor/gemini_executor.go
index 4b878ba53..70e3dcc7f 100644
--- a/internal/runtime/executor/gemini_executor.go
+++ b/internal/runtime/executor/gemini_executor.go
@@ -183,7 +183,7 @@ func (e *GeminiExecutor) Execute(ctx context.Context, auth *cliproxyauth.Auth, r
 	if apiKey != "" {
 		httpReq.Header.Set("x-goog-api-key", apiKey)
 	}
-	applyGeminiHeaders(httpReq, auth)
+	applyGeminiHeaders(httpReq, auth, opts.Headers)
 	var authID, authLabel, authType, authValue string
 	if auth != nil {
 		authID = auth.ID
@@ -295,7 +295,7 @@ func (e *GeminiExecutor) ExecuteStream(ctx context.Context, auth *cliproxyauth.A
 	if apiKey != "" {
 		httpReq.Header.Set("x-goog-api-key", apiKey)
 	}
-	applyGeminiHeaders(httpReq, auth)
+	applyGeminiHeaders(httpReq, auth, opts.Headers)
 	var authID, authLabel, authType, authValue string
 	if auth != nil {
 		authID = auth.ID
@@ -415,7 +415,7 @@ func (e *GeminiExecutor) executeInteractions(ctx context.Context, auth *cliproxy
 	if apiKey != "" {
 		httpReq.Header.Set("x-goog-api-key", apiKey)
 	}
-	applyGeminiHeaders(httpReq, auth)
+	applyGeminiHeaders(httpReq, auth, opts.Headers)
 	applyGeminiInteractionsRequestHeaders(httpReq, opts.Headers)
 	applyGeminiInteractionsRevisionHeader(httpReq)
 
@@ -495,7 +495,7 @@ func (e *GeminiExecutor) executeInteractionsStream(ctx context.Context, auth *cl
 	if apiKey != "" {
 		httpReq.Header.Set("x-goog-api-key", apiKey)
 	}
-	applyGeminiHeaders(httpReq, auth)
+	applyGeminiHeaders(httpReq, auth, opts.Headers)
 	applyGeminiInteractionsRequestHeaders(httpReq, opts.Headers)
 	applyGeminiInteractionsRevisionHeader(httpReq)
 
@@ -654,7 +654,7 @@ func (e *GeminiExecutor) CountTokens(ctx context.Context, auth *cliproxyauth.Aut
 	if apiKey != "" {
 		httpReq.Header.Set("x-goog-api-key", apiKey)
 	}
-	applyGeminiHeaders(httpReq, auth)
+	applyGeminiHeaders(httpReq, auth, opts.Headers)
 	var authID, authLabel, authType, authValue string
 	if auth != nil {
 		authID = auth.ID
@@ -896,12 +896,12 @@ func geminiAuthLogFields(auth *cliproxyauth.Auth) (string, string, string, strin
 	return auth.ID, auth.Label, authType, authValue
 }
 
-func applyGeminiHeaders(req *http.Request, auth *cliproxyauth.Auth) {
+func applyGeminiHeaders(req *http.Request, auth *cliproxyauth.Auth, clientHeaders ...http.Header) {
 	var attrs map[string]string
 	if auth != nil {
 		attrs = auth.Attributes
 	}
-	util.ApplyCustomHeadersFromAttrs(req, attrs)
+	util.ApplyCustomHeadersFromAttrs(req, attrs, clientHeaders...)
 }
 
 func capGeminiMaxOutputTokens(body []byte, modelName string) []byte {
diff --git a/internal/runtime/executor/gemini_vertex_executor.go b/internal/runtime/executor/gemini_vertex_executor.go
index 395ddf197..6d6eb8ffb 100644
--- a/internal/runtime/executor/gemini_vertex_executor.go
+++ b/internal/runtime/executor/gemini_vertex_executor.go
@@ -369,12 +369,12 @@ func (e *GeminiVertexExecutor) executeWithServiceAccount(ctx context.Context, au
 		log.Errorf("vertex executor: access token error: %v", errTok)
 		return resp, statusErr{code: 500, msg: "internal server error"}
 	}
-	applyGeminiHeaders(httpReq, auth)
+	applyGeminiHeaders(httpReq, auth, opts.Headers)
 	var attrs map[string]string
 	if auth != nil {
 		attrs = auth.Attributes
 	}
-	util.ApplyCustomHeadersFromAttrs(httpReq, attrs)
+	util.ApplyCustomHeadersFromAttrs(httpReq, attrs, opts.Headers)
 
 	var authID, authLabel, authType, authValue string
 	if auth != nil {
@@ -497,12 +497,12 @@ func (e *GeminiVertexExecutor) executeWithAPIKey(ctx context.Context, auth *clip
 	if apiKey != "" {
 		httpReq.Header.Set("x-goog-api-key", apiKey)
 	}
-	applyGeminiHeaders(httpReq, auth)
+	applyGeminiHeaders(httpReq, auth, opts.Headers)
 	var attrs map[string]string
 	if auth != nil {
 		attrs = auth.Attributes
 	}
-	util.ApplyCustomHeadersFromAttrs(httpReq, attrs)
+	util.ApplyCustomHeadersFromAttrs(httpReq, attrs, opts.Headers)
 
 	var authID, authLabel, authType, authValue string
 	if auth != nil {
@@ -614,12 +614,12 @@ func (e *GeminiVertexExecutor) executeStreamWithServiceAccount(ctx context.Conte
 		log.Errorf("vertex executor: access token error: %v", errTok)
 		return nil, statusErr{code: 500, msg: "internal server error"}
 	}
-	applyGeminiHeaders(httpReq, auth)
+	applyGeminiHeaders(httpReq, auth, opts.Headers)
 	var attrs map[string]string
 	if auth != nil {
 		attrs = auth.Attributes
 	}
-	util.ApplyCustomHeadersFromAttrs(httpReq, attrs)
+	util.ApplyCustomHeadersFromAttrs(httpReq, attrs, opts.Headers)
 
 	var authID, authLabel, authType, authValue string
 	if auth != nil {
@@ -761,12 +761,12 @@ func (e *GeminiVertexExecutor) executeStreamWithAPIKey(ctx context.Context, auth
 	if apiKey != "" {
 		httpReq.Header.Set("x-goog-api-key", apiKey)
 	}
-	applyGeminiHeaders(httpReq, auth)
+	applyGeminiHeaders(httpReq, auth, opts.Headers)
 	var attrs map[string]string
 	if auth != nil {
 		attrs = auth.Attributes
 	}
-	util.ApplyCustomHeadersFromAttrs(httpReq, attrs)
+	util.ApplyCustomHeadersFromAttrs(httpReq, attrs, opts.Headers)
 
 	var authID, authLabel, authType, authValue string
 	if auth != nil {
@@ -889,12 +889,12 @@ func (e *GeminiVertexExecutor) countTokensWithServiceAccount(ctx context.Context
 		log.Errorf("vertex executor: access token error: %v", errTok)
 		return cliproxyexecutor.Response{}, statusErr{code: 500, msg: "internal server error"}
 	}
-	applyGeminiHeaders(httpReq, auth)
+	applyGeminiHeaders(httpReq, auth, opts.Headers)
 	var attrs map[string]string
 	if auth != nil {
 		attrs = auth.Attributes
 	}
-	util.ApplyCustomHeadersFromAttrs(httpReq, attrs)
+	util.ApplyCustomHeadersFromAttrs(httpReq, attrs, opts.Headers)
 
 	var authID, authLabel, authType, authValue string
 	if auth != nil {
@@ -980,12 +980,12 @@ func (e *GeminiVertexExecutor) countTokensWithAPIKey(ctx context.Context, auth *
 	if apiKey != "" {
 		httpReq.Header.Set("x-goog-api-key", apiKey)
 	}
-	applyGeminiHeaders(httpReq, auth)
+	applyGeminiHeaders(httpReq, auth, opts.Headers)
 	var attrs map[string]string
 	if auth != nil {
 		attrs = auth.Attributes
 	}
-	util.ApplyCustomHeadersFromAttrs(httpReq, attrs)
+	util.ApplyCustomHeadersFromAttrs(httpReq, attrs, opts.Headers)
 
 	var authID, authLabel, authType, authValue string
 	if auth != nil {
diff --git a/internal/runtime/executor/openai_compat_executor.go b/internal/runtime/executor/openai_compat_executor.go
index 9429568d1..ee679d6d8 100644
--- a/internal/runtime/executor/openai_compat_executor.go
+++ b/internal/runtime/executor/openai_compat_executor.go
@@ -157,7 +157,7 @@ func (e *OpenAICompatExecutor) Execute(ctx context.Context, auth *cliproxyauth.A
 	if auth != nil {
 		attrs = auth.Attributes
 	}
-	util.ApplyCustomHeadersFromAttrs(httpReq, attrs)
+	util.ApplyCustomHeadersFromAttrs(httpReq, attrs, opts.Headers)
 	var authID, authLabel, authType, authValue string
 	if auth != nil {
 		authID = auth.ID
@@ -251,7 +251,7 @@ func (e *OpenAICompatExecutor) executeImages(ctx context.Context, auth *cliproxy
 	if auth != nil {
 		attrs = auth.Attributes
 	}
-	util.ApplyCustomHeadersFromAttrs(httpReq, attrs)
+	util.ApplyCustomHeadersFromAttrs(httpReq, attrs, opts.Headers)
 	var authID, authLabel, authType, authValue string
 	if auth != nil {
 		authID = auth.ID
@@ -369,7 +369,7 @@ func (e *OpenAICompatExecutor) ExecuteStream(ctx context.Context, auth *cliproxy
 	if auth != nil {
 		attrs = auth.Attributes
 	}
-	util.ApplyCustomHeadersFromAttrs(httpReq, attrs)
+	util.ApplyCustomHeadersFromAttrs(httpReq, attrs, opts.Headers)
 	httpReq.Header.Set("Accept", "text/event-stream")
 	httpReq.Header.Set("Cache-Control", "no-cache")
 	var authID, authLabel, authType, authValue string
@@ -608,7 +608,7 @@ func (e *OpenAICompatExecutor) executeImagesStream(ctx context.Context, auth *cl
 	if auth != nil {
 		attrs = auth.Attributes
 	}
-	util.ApplyCustomHeadersFromAttrs(httpReq, attrs)
+	util.ApplyCustomHeadersFromAttrs(httpReq, attrs, opts.Headers)
 	var authID, authLabel, authType, authValue string
 	if auth != nil {
 		authID = auth.ID
diff --git a/internal/runtime/executor/xai_executor_execute.go b/internal/runtime/executor/xai_executor_execute.go
index a7b59c8c8..72f769729 100644
--- a/internal/runtime/executor/xai_executor_execute.go
+++ b/internal/runtime/executor/xai_executor_execute.go
@@ -23,7 +23,7 @@ func (e *XAIExecutor) Execute(ctx context.Context, auth *cliproxyauth.Auth, req
 		return e.executeCompact(ctx, auth, req, opts)
 	}
 	if endpointPath := xaiImageEndpointPath(opts); endpointPath != "" {
-		return e.executeImages(ctx, auth, req, endpointPath)
+		return e.executeImages(ctx, auth, req, opts, endpointPath)
 	}
 	if xaiIsVideoRequest(opts) {
 		return e.executeVideos(ctx, auth, req, opts)
@@ -47,7 +47,7 @@ func (e *XAIExecutor) Execute(ctx context.Context, auth *cliproxyauth.Auth, req
 	if err != nil {
 		return resp, err
 	}
-	applyXAIChatHeaders(httpReq, auth, token, true, prepared.sessionID)
+	applyXAIChatHeaders(httpReq, auth, token, true, prepared.sessionID, opts.Headers)
 	e.recordXAIRequest(ctx, auth, url, httpReq.Header.Clone(), prepared.body)
 
 	httpClient := helps.NewProxyAwareHTTPClient(ctx, e.cfg, auth, 0)
@@ -159,7 +159,7 @@ func (e *XAIExecutor) executeCompactRequest(ctx context.Context, auth *cliproxya
 	}
 	// Official API / custom compact endpoints use standard API headers, not CLI
 	// chat-proxy identity headers (which applyXAIChatHeaders may still attach for OAuth chat).
-	applyXAIHeaders(httpReq, auth, token, false, prepared.sessionID)
+	applyXAIHeaders(httpReq, auth, token, false, prepared.sessionID, opts.Headers)
 	e.recordXAIRequest(ctx, auth, requestURL, httpReq.Header.Clone(), prepared.body)
 
 	httpClient := helps.NewProxyAwareHTTPClient(ctx, e.cfg, auth, 0)
diff --git a/internal/runtime/executor/xai_executor_media.go b/internal/runtime/executor/xai_executor_media.go
index 29128c8ab..f5df302d5 100644
--- a/internal/runtime/executor/xai_executor_media.go
+++ b/internal/runtime/executor/xai_executor_media.go
@@ -16,7 +16,7 @@ import (
 	"github.com/tidwall/gjson"
 )
 
-func (e *XAIExecutor) executeImages(ctx context.Context, auth *cliproxyauth.Auth, req cliproxyexecutor.Request, endpointPath string) (resp cliproxyexecutor.Response, err error) {
+func (e *XAIExecutor) executeImages(ctx context.Context, auth *cliproxyauth.Auth, req cliproxyexecutor.Request, opts cliproxyexecutor.Options, endpointPath string) (resp cliproxyexecutor.Response, err error) {
 	model := strings.TrimSpace(gjson.GetBytes(req.Payload, "model").String())
 	if model == "" {
 		model = strings.TrimSpace(req.Model)
@@ -39,7 +39,7 @@ func (e *XAIExecutor) executeImages(ctx context.Context, auth *cliproxyauth.Auth
 	if err != nil {
 		return resp, err
 	}
-	applyXAIHeaders(httpReq, auth, token, false, "")
+	applyXAIHeaders(httpReq, auth, token, false, "", opts.Headers)
 	e.recordXAIRequest(ctx, auth, url, httpReq.Header.Clone(), payload)
 
 	httpClient := helps.NewProxyAwareHTTPClient(ctx, e.cfg, auth, 0)
@@ -107,7 +107,7 @@ func (e *XAIExecutor) executeVideos(ctx context.Context, auth *cliproxyauth.Auth
 	if err != nil {
 		return resp, err
 	}
-	applyXAIHeaders(httpReq, auth, token, false, "")
+	applyXAIHeaders(httpReq, auth, token, false, "", opts.Headers)
 	if method == http.MethodPost {
 		key := xaiMetadataString(opts.Metadata, xaiIdempotencyKeyMetaKey)
 		if key == "" && opts.Headers != nil {
diff --git a/internal/runtime/executor/xai_executor_request.go b/internal/runtime/executor/xai_executor_request.go
index 6ee90d66f..04810dcbc 100644
--- a/internal/runtime/executor/xai_executor_request.go
+++ b/internal/runtime/executor/xai_executor_request.go
@@ -276,9 +276,9 @@ func logXAIResolvedBaseURL(ctx context.Context, baseURL string) {
 	helps.LogWithRequestID(ctx).Infof("xai: using base_url=%s source=%s", baseURL, xaiBaseURLSource(baseURL))
 }
 
-func applyXAIHeaders(r *http.Request, auth *cliproxyauth.Auth, token string, stream bool, sessionID string) {
+func applyXAIHeaders(r *http.Request, auth *cliproxyauth.Auth, token string, stream bool, sessionID string, clientHeaders ...http.Header) {
 	applyXAIDefaultHeaders(r, token, stream, sessionID)
-	applyXAICustomHeaders(r, auth)
+	applyXAICustomHeaders(r, auth, clientHeaders...)
 }
 
 func applyXAIDefaultHeaders(r *http.Request, token string, stream bool, sessionID string) {
@@ -297,12 +297,12 @@ func applyXAIDefaultHeaders(r *http.Request, token string, stream bool, sessionI
 	}
 }
 
-func applyXAICustomHeaders(r *http.Request, auth *cliproxyauth.Auth) {
+func applyXAICustomHeaders(r *http.Request, auth *cliproxyauth.Auth, clientHeaders ...http.Header) {
 	var attrs map[string]string
 	if auth != nil {
 		attrs = auth.Attributes
 	}
-	util.ApplyCustomHeadersFromAttrs(r, attrs)
+	util.ApplyCustomHeadersFromAttrs(r, attrs, clientHeaders...)
 }
 
 // applyXAIChatHeaders applies standard xAI headers for non-image/video chat
@@ -310,9 +310,9 @@ func applyXAICustomHeaders(r *http.Request, auth *cliproxyauth.Auth) {
 // applyXAIHeaders behavior. CLI chat-proxy identity headers are only attached
 // when using_api is false and the resolved chat base URL is the official CLI
 // chat-proxy endpoint.
-func applyXAIChatHeaders(r *http.Request, auth *cliproxyauth.Auth, token string, stream bool, sessionID string) {
+func applyXAIChatHeaders(r *http.Request, auth *cliproxyauth.Auth, token string, stream bool, sessionID string, clientHeaders ...http.Header) {
 	if xaiUsingAPI(auth) {
-		applyXAIHeaders(r, auth, token, stream, sessionID)
+		applyXAIHeaders(r, auth, token, stream, sessionID, clientHeaders...)
 		return
 	}
 	applyXAIDefaultHeaders(r, token, stream, sessionID)
@@ -323,7 +323,7 @@ func applyXAIChatHeaders(r *http.Request, auth *cliproxyauth.Auth, token string,
 		r.Header.Set(xaiClientIdentifierHeader, xaiClientIdentifierValue)
 		r.Header.Set(xaiAuthenticateResponseHeader, xaiAuthenticateResponseValue)
 	}
-	applyXAICustomHeaders(r, auth)
+	applyXAICustomHeaders(r, auth, clientHeaders...)
 }
 
 func xaiResolveComposerSessionID(ctx context.Context, req cliproxyexecutor.Request, opts cliproxyexecutor.Options, baseModel string) (string, error) {
diff --git a/internal/runtime/executor/xai_executor_stream.go b/internal/runtime/executor/xai_executor_stream.go
index 5ccbe292c..4dad2c51f 100644
--- a/internal/runtime/executor/xai_executor_stream.go
+++ b/internal/runtime/executor/xai_executor_stream.go
@@ -41,7 +41,7 @@ func (e *XAIExecutor) ExecuteStream(ctx context.Context, auth *cliproxyauth.Auth
 	if err != nil {
 		return nil, err
 	}
-	applyXAIChatHeaders(httpReq, auth, token, true, prepared.sessionID)
+	applyXAIChatHeaders(httpReq, auth, token, true, prepared.sessionID, opts.Headers)
 	e.recordXAIRequest(ctx, auth, url, httpReq.Header.Clone(), prepared.body)
 
 	httpClient := helps.NewProxyAwareHTTPClient(ctx, e.cfg, auth, 0)
diff --git a/internal/runtime/executor/xai_websockets_executor.go b/internal/runtime/executor/xai_websockets_executor.go
index f0d39b047..956046812 100644
--- a/internal/runtime/executor/xai_websockets_executor.go
+++ b/internal/runtime/executor/xai_websockets_executor.go
@@ -507,7 +507,7 @@ func (e *XAIWebsocketsExecutor) ExecuteStream(ctx context.Context, auth *cliprox
 	}
 	reporter.SetTranslatedReasoningEffort(prepared.body, e.Identifier())
 
-	wsHeaders := applyXAIWebsocketHeaders(http.Header{}, auth, token, prepared.sessionID)
+	wsHeaders := applyXAIWebsocketHeaders(http.Header{}, auth, token, prepared.sessionID, opts.Headers)
 	wsReqBody := buildXAIWebsocketRequestBody(prepared.body)
 	requestType := strings.TrimSpace(gjson.GetBytes(req.Payload, "type").String())
 	transcriptReset := strings.TrimSpace(gjson.GetBytes(wsReqBody, "previous_response_id").String()) == "" &&
@@ -1442,7 +1442,7 @@ func buildXAIResponsesWebsocketURL(httpURL string) (string, error) {
 	return parsed.String(), nil
 }
 
-func applyXAIWebsocketHeaders(headers http.Header, auth *cliproxyauth.Auth, token string, sessionID string) http.Header {
+func applyXAIWebsocketHeaders(headers http.Header, auth *cliproxyauth.Auth, token string, sessionID string, clientHeaders ...http.Header) http.Header {
 	if headers == nil {
 		headers = http.Header{}
 	}
@@ -1457,7 +1457,7 @@ func applyXAIWebsocketHeaders(headers http.Header, auth *cliproxyauth.Auth, toke
 	if auth != nil {
 		attrs = auth.Attributes
 	}
-	util.ApplyCustomHeadersFromAttrs(&http.Request{Header: headers}, attrs)
+	util.ApplyCustomHeadersFromAttrs(&http.Request{Header: headers}, attrs, clientHeaders...)
 	return headers
 }
 
diff --git a/internal/util/header_helpers.go b/internal/util/header_helpers.go
index 0b8d72bcb..f100fab80 100644
--- a/internal/util/header_helpers.go
+++ b/internal/util/header_helpers.go
@@ -3,18 +3,34 @@ package util
 import (
 	"net/http"
 	"strings"
+
+	"github.com/gin-gonic/gin"
 )
 
 // ApplyCustomHeadersFromAttrs applies user-defined headers stored in the provided attributes map.
 // Custom headers override built-in defaults when conflicts occur.
-func ApplyCustomHeadersFromAttrs(r *http.Request, attrs map[string]string) {
+// If clientHeaders is provided (or if the request context carries a Gin context), any custom header
+// whose value starts with "$" (e.g. "$ABC" or "$X-Claude-Code-Session-Id") is dynamically
+// resolved from the client's request headers. If the client did not provide that header,
+// the custom header is omitted from the outgoing request.
+func ApplyCustomHeadersFromAttrs(r *http.Request, attrs map[string]string, clientHeaders ...http.Header) {
 	if r == nil {
 		return
 	}
-	applyCustomHeaders(r, extractCustomHeaders(attrs))
+	var ch http.Header
+	if len(clientHeaders) > 0 && clientHeaders[0] != nil {
+		ch = clientHeaders[0]
+	} else if r.Context() != nil {
+		if ginCtx, ok := r.Context().Value("gin").(*gin.Context); ok && ginCtx != nil && ginCtx.Request != nil {
+			ch = ginCtx.Request.Header
+		} else if ginCtx, ok := r.Context().(*gin.Context); ok && ginCtx != nil && ginCtx.Request != nil {
+			ch = ginCtx.Request.Header
+		}
+	}
+	applyCustomHeaders(r, extractCustomHeaders(attrs, ch))
 }
 
-func extractCustomHeaders(attrs map[string]string) map[string]string {
+func extractCustomHeaders(attrs map[string]string, clientHeaders http.Header) map[string]string {
 	if len(attrs) == 0 {
 		return nil
 	}
@@ -31,6 +47,25 @@ func extractCustomHeaders(attrs map[string]string) map[string]string {
 		if val == "" {
 			continue
 		}
+		if strings.HasPrefix(val, "$") {
+			varName := strings.TrimSpace(strings.TrimPrefix(val, "$"))
+			if varName == "" || clientHeaders == nil {
+				continue
+			}
+			clientVal := clientHeaders.Get(varName)
+			if clientVal == "" {
+				for ck, cv := range clientHeaders {
+					if strings.EqualFold(ck, varName) && len(cv) > 0 && cv[0] != "" {
+						clientVal = cv[0]
+						break
+					}
+				}
+			}
+			if clientVal == "" {
+				continue
+			}
+			val = clientVal
+		}
 		headers[name] = val
 	}
 	if len(headers) == 0 {
diff --git a/internal/util/header_helpers_test.go b/internal/util/header_helpers_test.go
new file mode 100644
index 000000000..1f9d29ada
--- /dev/null
+++ b/internal/util/header_helpers_test.go
@@ -0,0 +1,116 @@
+package util
+
+import (
+	"net/http"
+	"net/http/httptest"
+	"testing"
+
+	"github.com/gin-gonic/gin"
+)
+
+func TestApplyCustomHeadersFromAttrs_StaticHeaders(t *testing.T) {
+	req := httptest.NewRequest(http.MethodPost, "https://api.example.com", nil)
+	attrs := map[string]string{
+		"header:X-Custom-Static": "static-value",
+		"header:Host":            "custom.host.com",
+	}
+
+	ApplyCustomHeadersFromAttrs(req, attrs)
+
+	if got := req.Header.Get("X-Custom-Static"); got != "static-value" {
+		t.Errorf("X-Custom-Static = %q, want %q", got, "static-value")
+	}
+	if got := req.Host; got != "custom.host.com" {
+		t.Errorf("req.Host = %q, want %q", got, "custom.host.com")
+	}
+}
+
+func TestApplyCustomHeadersFromAttrs_MagicVariable(t *testing.T) {
+	t.Run("present in clientHeaders sets header", func(t *testing.T) {
+		req := httptest.NewRequest(http.MethodPost, "https://api.example.com", nil)
+		attrs := map[string]string{
+			"header:X-Claude-Code-Session-Id": "$ABC",
+			"header:X-Target-Session":         "$X-Claude-Code-Session-Id",
+			"header:Static-Header":            "static-123",
+		}
+		clientHeaders := http.Header{
+			"Abc":                      []string{"session-abc-456"},
+			"X-Claude-Code-Session-Id": []string{"claude-code-uuid-789"},
+		}
+
+		ApplyCustomHeadersFromAttrs(req, attrs, clientHeaders)
+
+		if got := req.Header.Get("X-Claude-Code-Session-Id"); got != "session-abc-456" {
+			t.Errorf("X-Claude-Code-Session-Id = %q, want %q", got, "session-abc-456")
+		}
+		if got := req.Header.Get("X-Target-Session"); got != "claude-code-uuid-789" {
+			t.Errorf("X-Target-Session = %q, want %q", got, "claude-code-uuid-789")
+		}
+		if got := req.Header.Get("Static-Header"); got != "static-123" {
+			t.Errorf("Static-Header = %q, want %q", got, "static-123")
+		}
+	})
+
+	t.Run("absent in clientHeaders does not set header", func(t *testing.T) {
+		req := httptest.NewRequest(http.MethodPost, "https://api.example.com", nil)
+		attrs := map[string]string{
+			"header:X-Claude-Code-Session-Id": "$ABC",
+			"header:X-Other":                  "$NONEXISTENT",
+			"header:Static-Header":            "static-123",
+		}
+		clientHeaders := http.Header{
+			"Other-Header": []string{"some-value"},
+		}
+
+		ApplyCustomHeadersFromAttrs(req, attrs, clientHeaders)
+
+		if _, exists := req.Header["X-Claude-Code-Session-Id"]; exists {
+			t.Errorf("expected X-Claude-Code-Session-Id to be omitted when $ABC is absent in clientHeaders, got %q", req.Header.Get("X-Claude-Code-Session-Id"))
+		}
+		if _, exists := req.Header["X-Other"]; exists {
+			t.Errorf("expected X-Other to be omitted when $NONEXISTENT is absent in clientHeaders, got %q", req.Header.Get("X-Other"))
+		}
+		if got := req.Header.Get("Static-Header"); got != "static-123" {
+			t.Errorf("Static-Header = %q, want %q", got, "static-123")
+		}
+	})
+
+	t.Run("nil clientHeaders does not set variable headers", func(t *testing.T) {
+		req := httptest.NewRequest(http.MethodPost, "https://api.example.com", nil)
+		attrs := map[string]string{
+			"header:X-Claude-Code-Session-Id": "$ABC",
+			"header:Static-Header":            "static-123",
+		}
+
+		ApplyCustomHeadersFromAttrs(req, attrs)
+
+		if _, exists := req.Header["X-Claude-Code-Session-Id"]; exists {
+			t.Errorf("expected X-Claude-Code-Session-Id to be omitted with nil clientHeaders, got %q", req.Header.Get("X-Claude-Code-Session-Id"))
+		}
+		if got := req.Header.Get("Static-Header"); got != "static-123" {
+			t.Errorf("Static-Header = %q, want %q", got, "static-123")
+		}
+	})
+
+	t.Run("fallback to gin context in request context", func(t *testing.T) {
+		gin.SetMode(gin.TestMode)
+		w := httptest.NewRecorder()
+		ginCtx, _ := gin.CreateTestContext(w)
+		ginReq := httptest.NewRequest(http.MethodPost, "/", nil)
+		ginReq.Header.Set("ABC", "from-gin-ctx-123")
+		ginCtx.Request = ginReq
+
+		req := httptest.NewRequest(http.MethodPost, "https://api.example.com", nil)
+		req = req.WithContext(ginCtx)
+
+		attrs := map[string]string{
+			"header:X-Claude-Code-Session-Id": "$ABC",
+		}
+
+		ApplyCustomHeadersFromAttrs(req, attrs)
+
+		if got := req.Header.Get("X-Claude-Code-Session-Id"); got != "from-gin-ctx-123" {
+			t.Errorf("X-Claude-Code-Session-Id = %q, want %q", got, "from-gin-ctx-123")
+		}
+	})
+}