diff --git a/internal/skills/dep_installer.go b/internal/skills/dep_installer.go
index 140b6b40..fe8f596f 100644
--- a/internal/skills/dep_installer.go
+++ b/internal/skills/dep_installer.go
@@ -73,6 +73,9 @@ func InstallSingleDep(ctx context.Context, dep string) (bool, string) {
 		if err != nil {
 			msg := fmt.Sprintf("%s: %v", strings.TrimSpace(string(out)), err)
 			slog.Error("skills: dep install failed", "dep", dep, "error", msg)
+			if hint := pipBuildFailHint(pkg, string(out)); hint != "" {
+				slog.Warn("skills: dep install hint", "dep", dep, "hint", hint)
+			}
 			return false, msg
 		}
 	case strings.HasPrefix(dep, "npm:"):
@@ -141,6 +144,9 @@ func InstallDeps(ctx context.Context, manifest *SkillManifest, missing []string)
 			cmd := exec.CommandContext(ctx, "pip3", "install", "--no-cache-dir", "--break-system-packages", pkg)
 			if out, err := cmd.CombinedOutput(); err != nil {
 				result.Errors = append(result.Errors, fmt.Sprintf("pip %s: %s (%v)", pkg, strings.TrimSpace(string(out)), err))
+				if hint := pipBuildFailHint(pkg, string(out)); hint != "" {
+					slog.Warn("skills: dep install hint", "pkg", pkg, "hint", hint)
+				}
 			} else {
 				successful = append(successful, pkg)
 			}
diff --git a/internal/skills/dep_installer_hint.go b/internal/skills/dep_installer_hint.go
new file mode 100644
index 00000000..f0b59d0a
--- /dev/null
+++ b/internal/skills/dep_installer_hint.go
@@ -0,0 +1,32 @@
+package skills
+
+import "strings"
+
+// pipBuildFailHint returns a human-readable hint when a pip install fails
+// due to a build-from-source error (missing system lib or compiler).
+// Returns "" when no known pattern matches the combined stdout+stderr.
+//
+// Hints are log-side only — never returned to callers / HTTP responses —
+// so they can safely suggest alternatives without altering install semantics.
+// There is no auto-retry: failing packages typically have no wheel at all,
+// and a retry would burn the 5-minute install timeout uselessly.
+func pipBuildFailHint(pkg, combinedOutput string) string {
+	out := combinedOutput
+	if !strings.Contains(out, "Failed building wheel") &&
+		!strings.Contains(out, "Could not build wheels") &&
+		!strings.Contains(out, "pg_config") &&
+		!strings.Contains(out, "mysql_config") {
+		return ""
+	}
+	switch {
+	case strings.Contains(out, "pg_config"):
+		return "install 'pip:psycopg2-binary' (prebuilt wheel, no pg_config needed) or declare deps: in SKILL.md"
+	case strings.Contains(out, "mysql_config"):
+		return "install 'pip:PyMySQL' (pure-Python) or add 'system:mysql-dev' to deps: in SKILL.md"
+	case strings.Contains(pkg, "psycopg") && !strings.Contains(pkg, "binary"):
+		return "try 'pip:psycopg[binary]' (v3) or 'pip:psycopg2-binary' (v2) and declare explicitly in SKILL.md deps:"
+	case strings.Contains(pkg, "crypto") || strings.Contains(pkg, "Crypto"):
+		return "use 'pip:pycryptodome' (modern successor) and declare in SKILL.md deps:"
+	}
+	return "pip failed to build from source — try a '-binary' variant if available, or declare explicit deps: in SKILL.md"
+}
diff --git a/internal/skills/dep_installer_hint_test.go b/internal/skills/dep_installer_hint_test.go
new file mode 100644
index 00000000..4a9e2ce0
--- /dev/null
+++ b/internal/skills/dep_installer_hint_test.go
@@ -0,0 +1,84 @@
+package skills
+
+import (
+	"strings"
+	"testing"
+)
+
+func TestPipBuildFailHint(t *testing.T) {
+	cases := []struct {
+		name    string
+		pkg     string
+		output  string
+		wantSub string // substring expected in hint; "" = hint must be ""
+	}{
+		{
+			name:    "pg_config psycopg2",
+			pkg:     "psycopg2",
+			output:  "Error: pg_config executable not found. Failed building wheel for psycopg2",
+			wantSub: "psycopg2-binary",
+		},
+		{
+			name:    "mysql_config mysqlclient",
+			pkg:     "mysqlclient",
+			output:  "mysql_config not found... Failed building wheel for mysqlclient",
+			wantSub: "PyMySQL",
+		},
+		{
+			name:    "psycopg v3 no binary",
+			pkg:     "psycopg",
+			output:  "Failed building wheel for psycopg",
+			wantSub: "psycopg[binary]",
+		},
+		{
+			name:    "pycrypto old",
+			pkg:     "pycrypto",
+			output:  "Failed building wheel for pycrypto",
+			wantSub: "pycryptodome",
+		},
+		{
+			name:    "generic wheel fail",
+			pkg:     "somepkg",
+			output:  "ERROR: Could not build wheels for somepkg",
+			wantSub: "-binary",
+		},
+		{
+			name:    "success has no hint",
+			pkg:     "requests",
+			output:  "",
+			wantSub: "",
+		},
+		{
+			name:    "network error not build",
+			pkg:     "foo",
+			output:  "ERROR: Could not find a version that satisfies the requirement foo",
+			wantSub: "",
+		},
+		{
+			name:    "auth 403 not build",
+			pkg:     "internal-pkg",
+			output:  "ERROR: HTTP 403 Forbidden",
+			wantSub: "",
+		},
+		{
+			name:    "binary pkg already — no psycopg hint loop",
+			pkg:     "psycopg2-binary",
+			output:  "Failed building wheel for psycopg2-binary",
+			wantSub: "-binary",
+		},
+	}
+	for _, tc := range cases {
+		t.Run(tc.name, func(t *testing.T) {
+			got := pipBuildFailHint(tc.pkg, tc.output)
+			if tc.wantSub == "" {
+				if got != "" {
+					t.Errorf("expected empty hint, got %q", got)
+				}
+				return
+			}
+			if !strings.Contains(got, tc.wantSub) {
+				t.Errorf("hint %q does not contain %q", got, tc.wantSub)
+			}
+		})
+	}
+}