diff --git a/packages/dbt-tools/src/dbt-cli.ts b/packages/dbt-tools/src/dbt-cli.ts
index be9b92a97..77c4b6079 100644
--- a/packages/dbt-tools/src/dbt-cli.ts
+++ b/packages/dbt-tools/src/dbt-cli.ts
@@ -222,11 +222,16 @@ export async function execDbtShow(sql: string, limit?: number) {
   if (limit !== undefined) args.push("--limit", String(limit))
 
   let lines: Record<string, unknown>[]
+  // Capture the run() error so we can bubble the real dbt failure up if all
+  // parse tiers fail; the generic "Could not parse" alone misleads callers
+  // into treating structural project errors as transient.
+  let primaryRunError: ExecFileError | undefined
   try {
     const { stdout } = await run(args)
     lines = parseJsonLines(stdout)
-  } catch {
-    lines = []
+  } catch (e) {
+    primaryRunError = e as ExecFileError
+    lines = parseJsonLines(primaryRunError.stdout ?? "")
   }
 
   // --- Tier 1: known field paths ---
@@ -281,6 +286,7 @@ export async function execDbtShow(sql: string, limit?: number) {
   }
 
   // --- Tier 3: plain text fallback (ASCII table) ---
+  let plainRunError: ExecFileError | undefined
   try {
     const plainArgs = ["show", "--inline", sql]
     if (limit !== undefined) plainArgs.push("--limit", String(limit))
@@ -295,8 +301,15 @@ export async function execDbtShow(sql: string, limit?: number) {
         compiledSql: sql,
       }
     }
-  } catch {
-    // Plain text dbt show also failed — fall through to error below
+  } catch (e) {
+    plainRunError = e as ExecFileError
+  }
+
+  // If either run() rejected, dbt actually crashed — surface the real error
+  // instead of the generic "Could not parse" message.
+  const realError = extractDbtError(lines, primaryRunError, plainRunError)
+  if (realError) {
+    throw new Error(`dbt show failed: ${realError}`)
   }
 
   throw new Error(
@@ -305,6 +318,50 @@ export async function execDbtShow(sql: string, limit?: number) {
   )
 }
 
+/** Shape of an execFile rejection — carries stdout/stderr alongside message. */
+interface ExecFileError extends Error {
+  stdout?: string
+  stderr?: string
+  code?: number | string
+}
+
+/**
+ * Pick the best human-readable error from a failed `dbt show` invocation.
+ *
+ * Preference order:
+ *   1. A structured `level: "error"` event in the JSON log (dbt's own error msg).
+ *   2. Stderr from the JSON-mode run.
+ *   3. Stderr from the plain-text-mode run.
+ *   4. The exception message itself.
+ *
+ * Returns undefined if neither run rejected — caller falls back to the generic
+ * "Could not parse" message, which is correct when dbt exited 0 but emitted
+ * something we can't decode.
+ */
+function extractDbtError(
+  lines: Record<string, unknown>[],
+  primary?: ExecFileError,
+  plain?: ExecFileError,
+): string | undefined {
+  if (!primary && !plain) return undefined
+
+  const errorEvent = lines.find(
+    (l: any) => l.info?.level === "error" || l.level === "error",
+  ) as any
+  const structuredMsg = errorEvent?.info?.msg ?? errorEvent?.msg
+
+  const primaryStderr = primary?.stderr?.toString().trim()
+  const plainStderr = plain?.stderr?.toString().trim()
+
+  return (
+    (typeof structuredMsg === "string" && structuredMsg.length > 0 ? structuredMsg : undefined) ??
+    (primaryStderr && primaryStderr.length > 0 ? primaryStderr : undefined) ??
+    (plainStderr && plainStderr.length > 0 ? plainStderr : undefined) ??
+    primary?.message ??
+    plain?.message
+  )
+}
+
 /**
  * Compile a model via `dbt compile --select <model>` and return compiled SQL.
  */
diff --git a/packages/dbt-tools/test/dbt-cli.test.ts b/packages/dbt-tools/test/dbt-cli.test.ts
index e8c7c18eb..738f110e4 100644
--- a/packages/dbt-tools/test/dbt-cli.test.ts
+++ b/packages/dbt-tools/test/dbt-cli.test.ts
@@ -149,6 +149,73 @@ describe("execDbtShow", () => {
 
     await expect(execDbtShow("SELECT 1")).rejects.toThrow("Could not parse dbt show output in any format")
   })
+
+  // --- Bubble real dbt error instead of generic "Could not parse" ---
+
+  test("surfaces real dbt stderr when run fails", async () => {
+    mockExecFile.mockImplementation((_cmd: string, _args: string[], _opts: any, cb: Function) => {
+      const err: any = new Error("Command failed: dbt show --inline ...")
+      err.code = 1
+      err.stdout = ""
+      err.stderr =
+        "Runtime Error: Failed to read package: No dbt_project.yml found at expected path dbt_packages/dbt_utils/dbt_project.yml"
+      cb(err, err.stdout, err.stderr)
+    })
+
+    await expect(execDbtShow("SELECT 1")).rejects.toThrow(/Failed to read package/)
+    await expect(execDbtShow("SELECT 1")).rejects.toThrow(/dbt show failed/)
+  })
+
+  test("prefers structured error event in JSON log over raw stderr", async () => {
+    const errorLog = JSON.stringify({
+      info: {
+        level: "error",
+        msg: "Compilation Error: Model 'foo' depends on a node named 'bar' which was not found",
+      },
+    })
+    mockExecFile.mockImplementation((_cmd: string, _args: string[], _opts: any, cb: Function) => {
+      const err: any = new Error("Command failed")
+      err.code = 1
+      err.stdout = errorLog
+      err.stderr = "exit status 1"
+      cb(err, err.stdout, err.stderr)
+    })
+
+    await expect(execDbtShow("SELECT 1")).rejects.toThrow(/Compilation Error.*Model 'foo'/)
+  })
+
+  test("does not surface generic 'Could not parse' when dbt actually crashed", async () => {
+    mockExecFile.mockImplementation((_cmd: string, _args: string[], _opts: any, cb: Function) => {
+      const err: any = new Error("Command failed")
+      err.code = 2
+      err.stdout = ""
+      err.stderr = "Database Error: connection refused"
+      cb(err, err.stdout, err.stderr)
+    })
+
+    await expect(execDbtShow("SELECT 1")).rejects.not.toThrow(/Could not parse dbt show output/)
+  })
+
+  test("preserves generic 'Could not parse' when dbt exited 0 but output unparseable", async () => {
+    // Existing behavior — dbt didn't crash, we just couldn't decode its output.
+    mockExecFile.mockImplementation((_cmd: string, _args: string[], _opts: any, cb: Function) => {
+      cb(null, "some unparseable output", "")
+    })
+
+    await expect(execDbtShow("SELECT 1")).rejects.toThrow("Could not parse dbt show output in any format")
+  })
+
+  test("falls back to error message when stderr is empty", async () => {
+    mockExecFile.mockImplementation((_cmd: string, _args: string[], _opts: any, cb: Function) => {
+      const err: any = new Error("spawn ENOENT")
+      err.code = "ENOENT"
+      err.stdout = ""
+      err.stderr = ""
+      cb(err, "", "")
+    })
+
+    await expect(execDbtShow("SELECT 1")).rejects.toThrow(/spawn ENOENT|dbt show failed/)
+  })
 })
 
 // ---------------------------------------------------------------------------