diff --git a/workspace-server/internal/channels/discord.go b/workspace-server/internal/channels/discord.go
index 453007d9e..d4eb1d0c5 100644
--- a/workspace-server/internal/channels/discord.go
+++ b/workspace-server/internal/channels/discord.go
@@ -33,7 +33,12 @@ const (
 //
 // StartPolling returns nil immediately — Discord does not support long-polling;
 // use the Interactions webhook route instead.
-type DiscordAdapter struct{}
+type DiscordAdapter struct {
+	// httpClient overrides the default HTTP client used by SendMessage.
+	// Used in tests to inject a fake transport so token-redaction checks
+	// are deterministic and do not depend on real network behavior.
+	httpClient *http.Client
+}
 
 func (d *DiscordAdapter) Type() string        { return "discord" }
 func (d *DiscordAdapter) DisplayName() string { return "Discord" }
@@ -95,7 +100,10 @@ func (d *DiscordAdapter) SendMessage(ctx context.Context, config map[string]inte
 	// Split long messages into chunks at word boundaries where possible.
 	chunks := splitMessage(text, maxLen)
 
-	client := &http.Client{Timeout: discordHTTPTimeout}
+	client := d.httpClient
+	if client == nil {
+		client = &http.Client{Timeout: discordHTTPTimeout}
+	}
 	for _, chunk := range chunks {
 		payload, err := json.Marshal(map[string]string{"content": chunk})
 		if err != nil {
diff --git a/workspace-server/internal/channels/discord_test.go b/workspace-server/internal/channels/discord_test.go
index d2b79ff39..61c89f4df 100644
--- a/workspace-server/internal/channels/discord_test.go
+++ b/workspace-server/internal/channels/discord_test.go
@@ -3,6 +3,7 @@ package channels
 import (
 	"context"
 	"encoding/json"
+	"fmt"
 	"net/http"
 	"net/http/httptest"
 	"strings"
@@ -288,17 +289,25 @@ func TestSplitMessage_LongMessage(t *testing.T) {
 }
 
 // TestDiscordAdapter_SendMessage_ErrorDoesNotLeakToken verifies that when the
-// HTTP call to the Discord webhook fails (e.g. DNS error), the returned error
-// message does NOT contain the webhook URL — which embeds the Discord token.
+// HTTP call to the Discord webhook fails, the returned error message does NOT
+// contain the webhook URL — which embeds the Discord token.  Uses a fake
+// http.RoundTripper so the test is deterministic and does not depend on real
+// network behavior (fixes RCA #1763 Finding 2).
 // Regression test for the MEDIUM security finding in PR #659.
 func TestDiscordAdapter_SendMessage_ErrorDoesNotLeakToken(t *testing.T) {
-	a := &DiscordAdapter{}
-	// Use a valid-looking webhook URL with a fake token so we can check it
-	// doesn't appear in the error string.
 	fakeToken := "SUPER_SECRET_DISCORD_TOKEN_12345"
 	webhookURL := discordWebhookPrefix + "123456789/" + fakeToken
 
-	// Point at an unroutable address to force a dial error.
+	// Fake transport that returns an error containing the full webhook URL,
+	// mimicking the real behavior of net/http when a dial fails.
+	fakeTransport := roundTripperFunc(func(req *http.Request) (*http.Response, error) {
+		return nil, fmt.Errorf("dial tcp: connect to %s: connection refused", req.URL.String())
+	})
+
+	a := &DiscordAdapter{
+		httpClient: &http.Client{Transport: fakeTransport},
+	}
+
 	err := a.SendMessage(
 		context.Background(),
 		map[string]interface{}{"webhook_url": webhookURL},
@@ -307,14 +316,20 @@ func TestDiscordAdapter_SendMessage_ErrorDoesNotLeakToken(t *testing.T) {
 	)
 
 	if err == nil {
-		// In some environments the request might actually succeed; that's fine.
-		t.Skip("request unexpectedly succeeded — skipping token-leak check")
+		t.Fatal("expected error from fake transport, got nil")
 	}
 	if strings.Contains(err.Error(), fakeToken) {
 		t.Errorf("error message leaks Discord webhook token: %q", err.Error())
 	}
 }
 
+// roundTripperFunc adapts a function to the http.RoundTripper interface.
+type roundTripperFunc func(*http.Request) (*http.Response, error)
+
+func (f roundTripperFunc) RoundTrip(req *http.Request) (*http.Response, error) {
+	return f(req)
+}
+
 func TestSplitMessage_SplitsAtNewline(t *testing.T) {
 	// Build a message where a newline falls within the split window.
 	line1 := strings.Repeat("a", 1500) + "\n"