Enable local image prompts without breaking text-only CLI flows

The Rust CLI now recognizes explicit local image references in prompt text,
encodes supported image files as base64, and serializes mixed text/image
content blocks for the API. The request conversion path was kept narrow so
existing runtime/session structures remain stable while prompt mode and user
text conversion gain multimodal support.

Constraint: Must support PNG, JPG/JPEG, GIF, and WebP without adding broad runtime abstractions
Constraint: Existing text-only prompt behavior and API tool flows must keep working unchanged
Rejected: Add only explicit --image CLI flags | does not satisfy auto-detect image refs in prompt text
Rejected: Persist native image blocks in runtime session model | broader refactor than needed for prompt support
Confidence: high
Scope-risk: moderate
Reversibility: clean
Directive: Keep image parsing scoped to outbound user prompt adaptation unless session persistence truly needs multimodal history
Tested: cargo fmt --all; cargo clippy --workspace --all-targets -- -D warnings; cargo test --workspace
Not-tested: Live remote multimodal request against Anthropic API

rust/.omc/project-memory.json

@@ -1,127 +0,0 @@
-{
-  "version": "1.0.0",
-  "lastScanned": 1774971516826,
-  "projectRoot": "/home/bellman/Workspace/clawd-code-worktrees/api/rust",
-  "techStack": {
-    "languages": [
-      {
-        "name": "Rust",
-        "version": null,
-        "confidence": "high",
-        "markers": [
-          "Cargo.toml"
-        ]
-      }
-    ],
-    "frameworks": [],
-    "packageManager": "cargo",
-    "runtime": null
-  },
-  "build": {
-    "buildCommand": "cargo build",
-    "testCommand": "cargo test",
-    "lintCommand": "cargo clippy",
-    "devCommand": "cargo run",
-    "scripts": {}
-  },
-  "conventions": {
-    "namingStyle": null,
-    "importStyle": null,
-    "testPattern": null,
-    "fileOrganization": null
-  },
-  "structure": {
-    "isMonorepo": false,
-    "workspaces": [],
-    "mainDirectories": [],
-    "gitBranches": {
-      "defaultBranch": "main",
-      "branchingStrategy": null
-    }
-  },
-  "customNotes": [],
-  "directoryMap": {
-    "crates": {
-      "path": "crates",
-      "purpose": null,
-      "fileCount": 0,
-      "lastAccessed": 1774971516823,
-      "keyFiles": []
-    },
-    "target": {
-      "path": "target",
-      "purpose": null,
-      "fileCount": 2,
-      "lastAccessed": 1774971516823,
-      "keyFiles": [
-        "CACHEDIR.TAG"
-      ]
-    },
-    "crates/api": {
-      "path": "crates/api",
-      "purpose": "API routes",
-      "fileCount": 1,
-      "lastAccessed": 1774971516824,
-      "keyFiles": [
-        "Cargo.toml"
-      ]
-    }
-  },
-  "hotPaths": [
-    {
-      "path": "crates/api/Cargo.toml",
-      "accessCount": 1,
-      "lastAccessed": 1774971547109,
-      "type": "file"
-    },
-    {
-      "path": "crates/api/src/lib.rs",
-      "accessCount": 1,
-      "lastAccessed": 1774971547624,
-      "type": "file"
-    },
-    {
-      "path": "crates/api/src/client.rs",
-      "accessCount": 1,
-      "lastAccessed": 1774971548001,
-      "type": "file"
-    },
-    {
-      "path": "crates/api/src/error.rs",
-      "accessCount": 1,
-      "lastAccessed": 1774971548503,
-      "type": "file"
-    },
-    {
-      "path": "crates/api/src/sse.rs",
-      "accessCount": 1,
-      "lastAccessed": 1774971549311,
-      "type": "file"
-    },
-    {
-      "path": "crates/api/src/types.rs",
-      "accessCount": 1,
-      "lastAccessed": 1774971549472,
-      "type": "file"
-    },
-    {
-      "path": "crates/api/tests/client_integration.rs",
-      "accessCount": 1,
-      "lastAccessed": 1774971550143,
-      "type": "file"
-    },
-    {
-      "path": "Cargo.toml",
-      "accessCount": 1,
-      "lastAccessed": 1774971550539,
-      "type": "file"
-    },
-    {
-      "path": "crates/rusty-claude-cli/src/main.rs",
-      "accessCount": 1,
-      "lastAccessed": 1774971551474,
-      "type": "file"
-    }
-  ],
-  "userDirectives": []
-}

rust/.omc/state/idle-notif-cooldown.json

@@ -1,3 +0,0 @@
-{
-  "lastSentAt": "2026-03-31T15:39:44.771Z"
-}

rust/README.md

@@ -109,13 +109,6 @@ cd rust
 cargo run -p rusty-claude-cli -- --allowedTools read,glob
 ```
 
-Bootstrap Claude project files for the current repo:
-
-```bash
-cd rust
-cargo run -p rusty-claude-cli -- init
-```
-
 ### 2) REPL mode
 
 Start the interactive shell:
@@ -186,7 +179,7 @@ cargo run -p rusty-claude-cli -- --resume session.json /memory /config
 - `/resume <session-path>` — load a saved session into the REPL
 - `/config [env|hooks|model]` — inspect discovered Claude config
 - `/memory` — inspect loaded instruction memory files
-- `/init` — bootstrap `.claude.json`, `.claude/`, `CLAUDE.md`, and local ignore rules
+- `/init` — create a starter `CLAUDE.md`
 - `/diff` — show the current git diff for the workspace
 - `/version` — print version and build metadata locally
 - `/export [file]` — export the current conversation transcript

rust/crates/api/src/lib.rs

@@ -11,7 +11,7 @@ pub use error::ApiError;
 pub use sse::{parse_frame, SseParser};
 pub use types::{
     ContentBlockDelta, ContentBlockDeltaEvent, ContentBlockStartEvent, ContentBlockStopEvent,
-    InputContentBlock, InputMessage, MessageDelta, MessageDeltaEvent, MessageRequest,
+    ImageSource, InputContentBlock, InputMessage, MessageDelta, MessageDeltaEvent, MessageRequest,
     MessageResponse, MessageStartEvent, MessageStopEvent, OutputContentBlock, StreamEvent,
     ToolChoice, ToolDefinition, ToolResultContentBlock, Usage,
 };

rust/crates/api/src/types.rs

@@ -64,6 +64,9 @@ pub enum InputContentBlock {
     Text {
         text: String,
     },
+    Image {
+        source: ImageSource,
+    },
     ToolUse {
         id: String,
         name: String,
@@ -77,6 +80,14 @@ pub enum InputContentBlock {
     },
 }
 
+#[derive(Debug, Clone, PartialEq, Eq, Serialize, Deserialize)]
+pub struct ImageSource {
+    #[serde(rename = "type")]
+    pub kind: String,
+    pub media_type: String,
+    pub data: String,
+}
+
 #[derive(Debug, Clone, PartialEq, Serialize, Deserialize)]
 #[serde(tag = "type", rename_all = "snake_case")]
 pub enum ToolResultContentBlock {

rust/crates/api/tests/client_integration.rs

@@ -4,8 +4,8 @@ use std::time::Duration;
 
 use api::{
     AnthropicClient, ApiError, ContentBlockDelta, ContentBlockDeltaEvent, ContentBlockStartEvent,
-    InputContentBlock, InputMessage, MessageDeltaEvent, MessageRequest, OutputContentBlock,
-    StreamEvent, ToolChoice, ToolDefinition,
+    ImageSource, InputContentBlock, InputMessage, MessageDeltaEvent, MessageRequest,
+    OutputContentBlock, StreamEvent, ToolChoice, ToolDefinition,
 };
 use serde_json::json;
 use tokio::io::{AsyncReadExt, AsyncWriteExt};
@@ -75,6 +75,39 @@ async fn send_message_posts_json_and_parses_response() {
     assert_eq!(body["tool_choice"]["type"], json!("auto"));
 }
 
+#[test]
+fn image_content_blocks_serialize_with_base64_source() {
+    let request = MessageRequest {
+        model: "claude-3-7-sonnet-latest".to_string(),
+        max_tokens: 64,
+        messages: vec![InputMessage {
+            role: "user".to_string(),
+            content: vec![InputContentBlock::Image {
+                source: ImageSource {
+                    kind: "base64".to_string(),
+                    media_type: "image/png".to_string(),
+                    data: "AQID".to_string(),
+                },
+            }],
+        }],
+        system: None,
+        tools: None,
+        tool_choice: None,
+        stream: false,
+    };
+
+    let json = serde_json::to_value(request).expect("request should serialize");
+    assert_eq!(json["messages"][0]["content"][0]["type"], json!("image"));
+    assert_eq!(
+        json["messages"][0]["content"][0]["source"],
+        json!({
+            "type": "base64",
+            "media_type": "image/png",
+            "data": "AQID"
+        })
+    );
+}
+
 #[tokio::test]
 async fn stream_message_parses_sse_events_with_tool_use() {
     let state = Arc::new(Mutex::new(Vec::<CapturedRequest>::new()));

rust/crates/commands/src/lib.rs

@@ -101,7 +101,7 @@ const SLASH_COMMAND_SPECS: &[SlashCommandSpec] = &[
     },
     SlashCommandSpec {
         name: "init",
-        summary: "Bootstrap Claude project files for this repo",
+        summary: "Create a starter CLAUDE.md for this repo",
         argument_hint: None,
         resume_supported: true,
     },

rust/crates/rusty-claude-cli/src/init.rs

@@ -1,433 +0,0 @@
-use std::fs;
-use std::path::{Path, PathBuf};
-
-const STARTER_CLAUDE_JSON: &str = concat!(
-    "{\n",
-    "  \"permissions\": {\n",
-    "    \"defaultMode\": \"acceptEdits\"\n",
-    "  }\n",
-    "}\n",
-);
-const GITIGNORE_COMMENT: &str = "# Claude Code local artifacts";
-const GITIGNORE_ENTRIES: [&str; 2] = [".claude/settings.local.json", ".claude/sessions/"];
-
-#[derive(Debug, Clone, Copy, PartialEq, Eq)]
-pub(crate) enum InitStatus {
-    Created,
-    Updated,
-    Skipped,
-}
-
-impl InitStatus {
-    #[must_use]
-    pub(crate) fn label(self) -> &'static str {
-        match self {
-            Self::Created => "created",
-            Self::Updated => "updated",
-            Self::Skipped => "skipped (already exists)",
-        }
-    }
-}
-
-#[derive(Debug, Clone, PartialEq, Eq)]
-pub(crate) struct InitArtifact {
-    pub(crate) name: &'static str,
-    pub(crate) status: InitStatus,
-}
-
-#[derive(Debug, Clone, PartialEq, Eq)]
-pub(crate) struct InitReport {
-    pub(crate) project_root: PathBuf,
-    pub(crate) artifacts: Vec<InitArtifact>,
-}
-
-impl InitReport {
-    #[must_use]
-    pub(crate) fn render(&self) -> String {
-        let mut lines = vec![
-            "Init".to_string(),
-            format!("  Project          {}", self.project_root.display()),
-        ];
-        for artifact in &self.artifacts {
-            lines.push(format!(
-                "  {:<16} {}",
-                artifact.name,
-                artifact.status.label()
-            ));
-        }
-        lines.push("  Next step        Review and tailor the generated guidance".to_string());
-        lines.join("\n")
-    }
-}
-
-#[derive(Debug, Clone, Default, PartialEq, Eq)]
-#[allow(clippy::struct_excessive_bools)]
-struct RepoDetection {
-    rust_workspace: bool,
-    rust_root: bool,
-    python: bool,
-    package_json: bool,
-    typescript: bool,
-    nextjs: bool,
-    react: bool,
-    vite: bool,
-    nest: bool,
-    src_dir: bool,
-    tests_dir: bool,
-    rust_dir: bool,
-}
-
-pub(crate) fn initialize_repo(cwd: &Path) -> Result<InitReport, Box<dyn std::error::Error>> {
-    let mut artifacts = Vec::new();
-
-    let claude_dir = cwd.join(".claude");
-    artifacts.push(InitArtifact {
-        name: ".claude/",
-        status: ensure_dir(&claude_dir)?,
-    });
-
-    let claude_json = cwd.join(".claude.json");
-    artifacts.push(InitArtifact {
-        name: ".claude.json",
-        status: write_file_if_missing(&claude_json, STARTER_CLAUDE_JSON)?,
-    });
-
-    let gitignore = cwd.join(".gitignore");
-    artifacts.push(InitArtifact {
-        name: ".gitignore",
-        status: ensure_gitignore_entries(&gitignore)?,
-    });
-
-    let claude_md = cwd.join("CLAUDE.md");
-    let content = render_init_claude_md(cwd);
-    artifacts.push(InitArtifact {
-        name: "CLAUDE.md",
-        status: write_file_if_missing(&claude_md, &content)?,
-    });
-
-    Ok(InitReport {
-        project_root: cwd.to_path_buf(),
-        artifacts,
-    })
-}
-
-fn ensure_dir(path: &Path) -> Result<InitStatus, std::io::Error> {
-    if path.is_dir() {
-        return Ok(InitStatus::Skipped);
-    }
-    fs::create_dir_all(path)?;
-    Ok(InitStatus::Created)
-}
-
-fn write_file_if_missing(path: &Path, content: &str) -> Result<InitStatus, std::io::Error> {
-    if path.exists() {
-        return Ok(InitStatus::Skipped);
-    }
-    fs::write(path, content)?;
-    Ok(InitStatus::Created)
-}
-
-fn ensure_gitignore_entries(path: &Path) -> Result<InitStatus, std::io::Error> {
-    if !path.exists() {
-        let mut lines = vec![GITIGNORE_COMMENT.to_string()];
-        lines.extend(GITIGNORE_ENTRIES.iter().map(|entry| (*entry).to_string()));
-        fs::write(path, format!("{}\n", lines.join("\n")))?;
-        return Ok(InitStatus::Created);
-    }
-
-    let existing = fs::read_to_string(path)?;
-    let mut lines = existing.lines().map(ToOwned::to_owned).collect::<Vec<_>>();
-    let mut changed = false;
-
-    if !lines.iter().any(|line| line == GITIGNORE_COMMENT) {
-        lines.push(GITIGNORE_COMMENT.to_string());
-        changed = true;
-    }
-
-    for entry in GITIGNORE_ENTRIES {
-        if !lines.iter().any(|line| line == entry) {
-            lines.push(entry.to_string());
-            changed = true;
-        }
-    }
-
-    if !changed {
-        return Ok(InitStatus::Skipped);
-    }
-
-    fs::write(path, format!("{}\n", lines.join("\n")))?;
-    Ok(InitStatus::Updated)
-}
-
-pub(crate) fn render_init_claude_md(cwd: &Path) -> String {
-    let detection = detect_repo(cwd);
-    let mut lines = vec![
-        "# CLAUDE.md".to_string(),
-        String::new(),
-        "This file provides guidance to Claude Code (claude.ai/code) when working with code in this repository.".to_string(),
-        String::new(),
-    ];
-
-    let detected_languages = detected_languages(&detection);
-    let detected_frameworks = detected_frameworks(&detection);
-    lines.push("## Detected stack".to_string());
-    if detected_languages.is_empty() {
-        lines.push("- No specific language markers were detected yet; document the primary language and verification commands once the project structure settles.".to_string());
-    } else {
-        lines.push(format!("- Languages: {}.", detected_languages.join(", ")));
-    }
-    if detected_frameworks.is_empty() {
-        lines.push("- Frameworks: none detected from the supported starter markers.".to_string());
-    } else {
-        lines.push(format!(
-            "- Frameworks/tooling markers: {}.",
-            detected_frameworks.join(", ")
-        ));
-    }
-    lines.push(String::new());
-
-    let verification_lines = verification_lines(cwd, &detection);
-    if !verification_lines.is_empty() {
-        lines.push("## Verification".to_string());
-        lines.extend(verification_lines);
-        lines.push(String::new());
-    }
-
-    let structure_lines = repository_shape_lines(&detection);
-    if !structure_lines.is_empty() {
-        lines.push("## Repository shape".to_string());
-        lines.extend(structure_lines);
-        lines.push(String::new());
-    }
-
-    let framework_lines = framework_notes(&detection);
-    if !framework_lines.is_empty() {
-        lines.push("## Framework notes".to_string());
-        lines.extend(framework_lines);
-        lines.push(String::new());
-    }
-
-    lines.push("## Working agreement".to_string());
-    lines.push("- Prefer small, reviewable changes and keep generated bootstrap files aligned with actual repo workflows.".to_string());
-    lines.push("- Keep shared defaults in `.claude.json`; reserve `.claude/settings.local.json` for machine-local overrides.".to_string());
-    lines.push("- Do not overwrite existing `CLAUDE.md` content automatically; update it intentionally when repo workflows change.".to_string());
-    lines.push(String::new());
-
-    lines.join("\n")
-}
-
-fn detect_repo(cwd: &Path) -> RepoDetection {
-    let package_json_contents = fs::read_to_string(cwd.join("package.json"))
-        .unwrap_or_default()
-        .to_ascii_lowercase();
-    RepoDetection {
-        rust_workspace: cwd.join("rust").join("Cargo.toml").is_file(),
-        rust_root: cwd.join("Cargo.toml").is_file(),
-        python: cwd.join("pyproject.toml").is_file()
-            || cwd.join("requirements.txt").is_file()
-            || cwd.join("setup.py").is_file(),
-        package_json: cwd.join("package.json").is_file(),
-        typescript: cwd.join("tsconfig.json").is_file()
-            || package_json_contents.contains("typescript"),
-        nextjs: package_json_contents.contains("\"next\""),
-        react: package_json_contents.contains("\"react\""),
-        vite: package_json_contents.contains("\"vite\""),
-        nest: package_json_contents.contains("@nestjs"),
-        src_dir: cwd.join("src").is_dir(),
-        tests_dir: cwd.join("tests").is_dir(),
-        rust_dir: cwd.join("rust").is_dir(),
-    }
-}
-
-fn detected_languages(detection: &RepoDetection) -> Vec<&'static str> {
-    let mut languages = Vec::new();
-    if detection.rust_workspace || detection.rust_root {
-        languages.push("Rust");
-    }
-    if detection.python {
-        languages.push("Python");
-    }
-    if detection.typescript {
-        languages.push("TypeScript");
-    } else if detection.package_json {
-        languages.push("JavaScript/Node.js");
-    }
-    languages
-}
-
-fn detected_frameworks(detection: &RepoDetection) -> Vec<&'static str> {
-    let mut frameworks = Vec::new();
-    if detection.nextjs {
-        frameworks.push("Next.js");
-    }
-    if detection.react {
-        frameworks.push("React");
-    }
-    if detection.vite {
-        frameworks.push("Vite");
-    }
-    if detection.nest {
-        frameworks.push("NestJS");
-    }
-    frameworks
-}
-
-fn verification_lines(cwd: &Path, detection: &RepoDetection) -> Vec<String> {
-    let mut lines = Vec::new();
-    if detection.rust_workspace {
-        lines.push("- Run Rust verification from `rust/`: `cargo fmt`, `cargo clippy --workspace --all-targets -- -D warnings`, `cargo test --workspace`".to_string());
-    } else if detection.rust_root {
-        lines.push("- Run Rust verification from the repo root: `cargo fmt`, `cargo clippy --workspace --all-targets -- -D warnings`, `cargo test --workspace`".to_string());
-    }
-    if detection.python {
-        if cwd.join("pyproject.toml").is_file() {
-            lines.push("- Run the Python project checks declared in `pyproject.toml` (for example: `pytest`, `ruff check`, and `mypy` when configured).".to_string());
-        } else {
-            lines.push(
-                "- Run the repo's Python test/lint commands before shipping changes.".to_string(),
-            );
-        }
-    }
-    if detection.package_json {
-        lines.push("- Run the JavaScript/TypeScript checks from `package.json` before shipping changes (`npm test`, `npm run lint`, `npm run build`, or the repo equivalent).".to_string());
-    }
-    if detection.tests_dir && detection.src_dir {
-        lines.push("- `src/` and `tests/` are both present; update both surfaces together when behavior changes.".to_string());
-    }
-    lines
-}
-
-fn repository_shape_lines(detection: &RepoDetection) -> Vec<String> {
-    let mut lines = Vec::new();
-    if detection.rust_dir {
-        lines.push(
-            "- `rust/` contains the Rust workspace and active CLI/runtime implementation."
-                .to_string(),
-        );
-    }
-    if detection.src_dir {
-        lines.push("- `src/` contains source files that should stay consistent with generated guidance and tests.".to_string());
-    }
-    if detection.tests_dir {
-        lines.push("- `tests/` contains validation surfaces that should be reviewed alongside code changes.".to_string());
-    }
-    lines
-}
-
-fn framework_notes(detection: &RepoDetection) -> Vec<String> {
-    let mut lines = Vec::new();
-    if detection.nextjs {
-        lines.push("- Next.js detected: preserve routing/data-fetching conventions and verify production builds after changing app structure.".to_string());
-    }
-    if detection.react && !detection.nextjs {
-        lines.push("- React detected: keep component behavior covered with focused tests and avoid unnecessary prop/API churn.".to_string());
-    }
-    if detection.vite {
-        lines.push("- Vite detected: validate the production bundle after changing build-sensitive configuration or imports.".to_string());
-    }
-    if detection.nest {
-        lines.push("- NestJS detected: keep module/provider boundaries explicit and verify controller/service wiring after refactors.".to_string());
-    }
-    lines
-}
-
-#[cfg(test)]
-mod tests {
-    use super::{initialize_repo, render_init_claude_md};
-    use std::fs;
-    use std::path::Path;
-    use std::time::{SystemTime, UNIX_EPOCH};
-
-    fn temp_dir() -> std::path::PathBuf {
-        let nanos = SystemTime::now()
-            .duration_since(UNIX_EPOCH)
-            .expect("time should be after epoch")
-            .as_nanos();
-        std::env::temp_dir().join(format!("rusty-claude-init-{nanos}"))
-    }
-
-    #[test]
-    fn initialize_repo_creates_expected_files_and_gitignore_entries() {
-        let root = temp_dir();
-        fs::create_dir_all(root.join("rust")).expect("create rust dir");
-        fs::write(root.join("rust").join("Cargo.toml"), "[workspace]\n").expect("write cargo");
-
-        let report = initialize_repo(&root).expect("init should succeed");
-        let rendered = report.render();
-        assert!(rendered.contains(".claude/         created"));
-        assert!(rendered.contains(".claude.json     created"));
-        assert!(rendered.contains(".gitignore       created"));
-        assert!(rendered.contains("CLAUDE.md        created"));
-        assert!(root.join(".claude").is_dir());
-        assert!(root.join(".claude.json").is_file());
-        assert!(root.join("CLAUDE.md").is_file());
-        assert_eq!(
-            fs::read_to_string(root.join(".claude.json")).expect("read claude json"),
-            concat!(
-                "{\n",
-                "  \"permissions\": {\n",
-                "    \"defaultMode\": \"acceptEdits\"\n",
-                "  }\n",
-                "}\n",
-            )
-        );
-        let gitignore = fs::read_to_string(root.join(".gitignore")).expect("read gitignore");
-        assert!(gitignore.contains(".claude/settings.local.json"));
-        assert!(gitignore.contains(".claude/sessions/"));
-        let claude_md = fs::read_to_string(root.join("CLAUDE.md")).expect("read claude md");
-        assert!(claude_md.contains("Languages: Rust."));
-        assert!(claude_md.contains("cargo clippy --workspace --all-targets -- -D warnings"));
-
-        fs::remove_dir_all(root).expect("cleanup temp dir");
-    }
-
-    #[test]
-    fn initialize_repo_is_idempotent_and_preserves_existing_files() {
-        let root = temp_dir();
-        fs::create_dir_all(&root).expect("create root");
-        fs::write(root.join("CLAUDE.md"), "custom guidance\n").expect("write existing claude md");
-        fs::write(root.join(".gitignore"), ".claude/settings.local.json\n")
-            .expect("write gitignore");
-
-        let first = initialize_repo(&root).expect("first init should succeed");
-        assert!(first
-            .render()
-            .contains("CLAUDE.md        skipped (already exists)"));
-        let second = initialize_repo(&root).expect("second init should succeed");
-        let second_rendered = second.render();
-        assert!(second_rendered.contains(".claude/         skipped (already exists)"));
-        assert!(second_rendered.contains(".claude.json     skipped (already exists)"));
-        assert!(second_rendered.contains(".gitignore       skipped (already exists)"));
-        assert!(second_rendered.contains("CLAUDE.md        skipped (already exists)"));
-        assert_eq!(
-            fs::read_to_string(root.join("CLAUDE.md")).expect("read existing claude md"),
-            "custom guidance\n"
-        );
-        let gitignore = fs::read_to_string(root.join(".gitignore")).expect("read gitignore");
-        assert_eq!(gitignore.matches(".claude/settings.local.json").count(), 1);
-        assert_eq!(gitignore.matches(".claude/sessions/").count(), 1);
-
-        fs::remove_dir_all(root).expect("cleanup temp dir");
-    }
-
-    #[test]
-    fn render_init_template_mentions_detected_python_and_nextjs_markers() {
-        let root = temp_dir();
-        fs::create_dir_all(&root).expect("create root");
-        fs::write(root.join("pyproject.toml"), "[project]\nname = \"demo\"\n")
-            .expect("write pyproject");
-        fs::write(
-            root.join("package.json"),
-            r#"{"dependencies":{"next":"14.0.0","react":"18.0.0"},"devDependencies":{"typescript":"5.0.0"}}"#,
-        )
-        .expect("write package json");
-
-        let rendered = render_init_claude_md(Path::new(&root));
-        assert!(rendered.contains("Languages: Python, TypeScript."));
-        assert!(rendered.contains("Frameworks/tooling markers: Next.js, React."));
-        assert!(rendered.contains("pyproject.toml"));
-        assert!(rendered.contains("Next.js detected"));
-
-        fs::remove_dir_all(root).expect("cleanup temp dir");
-    }
-}

rust/crates/rusty-claude-cli/src/main.rs

@@ -1,4 +1,3 @@
-mod init;
 mod input;
 mod render;
 
@@ -12,8 +11,8 @@ use std::process::Command;
 use std::time::{SystemTime, UNIX_EPOCH};
 
 use api::{
-    resolve_startup_auth_source, AnthropicClient, AuthSource, ContentBlockDelta, InputContentBlock,
-    InputMessage, MessageRequest, MessageResponse, OutputContentBlock,
+    resolve_startup_auth_source, AnthropicClient, AuthSource, ContentBlockDelta, ImageSource,
+    InputContentBlock, InputMessage, MessageRequest, MessageResponse, OutputContentBlock,
     StreamEvent as ApiStreamEvent, ToolChoice, ToolDefinition, ToolResultContentBlock,
 };
 
@@ -21,7 +20,6 @@ use commands::{
     render_slash_command_help, resume_supported_slash_commands, slash_command_specs, SlashCommand,
 };
 use compat_harness::{extract_manifest, UpstreamPaths};
-use init::initialize_repo;
 use render::{Spinner, TerminalRenderer};
 use runtime::{
     clear_oauth_credentials, generate_pkce_pair, generate_state, load_system_prompt,
@@ -43,6 +41,7 @@ const BUILD_TARGET: Option<&str> = option_env!("TARGET");
 const GIT_SHA: Option<&str> = option_env!("GIT_SHA");
 
 type AllowedToolSet = BTreeSet<String>;
+const IMAGE_REF_PREFIX: &str = "@";
 
 fn main() {
     if let Err(error) = run() {
@@ -76,7 +75,6 @@ fn run() -> Result<(), Box<dyn std::error::Error>> {
             .run_turn_with_output(&prompt, output_format)?,
         CliAction::Login => run_login()?,
         CliAction::Logout => run_logout()?,
-        CliAction::Init => run_init()?,
         CliAction::Repl {
             model,
             allowed_tools,
@@ -109,7 +107,6 @@ enum CliAction {
     },
     Login,
     Logout,
-    Init,
     Repl {
         model: String,
         allowed_tools: Option<AllowedToolSet>,
@@ -234,7 +231,6 @@ fn parse_args(args: &[String]) -> Result<CliAction, String> {
         "system-prompt" => parse_system_prompt_args(&rest[1..]),
         "login" => Ok(CliAction::Login),
         "logout" => Ok(CliAction::Logout),
-        "init" => Ok(CliAction::Init),
         "prompt" => {
             let prompt = rest[1..].join(" ");
             if prompt.trim().is_empty() {
@@ -708,6 +704,26 @@ fn format_resume_report(session_path: &str, message_count: usize, turns: u32) ->
     )
 }
 
+fn format_init_report(path: &Path, created: bool) -> String {
+    if created {
+        format!(
+            "Init
+  CLAUDE.md        {}
+  Result           created
+  Next step        Review and tailor the generated guidance",
+            path.display()
+        )
+    } else {
+        format!(
+            "Init
+  CLAUDE.md        {}
+  Result           skipped (already exists)
+  Next step        Edit the existing file intentionally if workflows changed",
+            path.display()
+        )
+    }
+}
+
 fn format_compact_report(removed: usize, resulting_messages: usize, skipped: bool) -> String {
     if skipped {
         format!(
@@ -1027,9 +1043,7 @@ impl LiveCli {
             max_tokens: DEFAULT_MAX_TOKENS,
             messages: vec![InputMessage {
                 role: "user".to_string(),
-                content: vec![InputContentBlock::Text {
-                    text: input.to_string(),
-                }],
+                content: prompt_to_content_blocks(input, &env::current_dir()?)?,
             }],
             system: (!self.system_prompt.is_empty()).then(|| self.system_prompt.join("\n\n")),
             tools: None,
@@ -1097,7 +1111,7 @@ impl LiveCli {
                 false
             }
             SlashCommand::Init => {
-                run_init()?;
+                Self::run_init()?;
                 false
             }
             SlashCommand::Diff => {
@@ -1305,6 +1319,11 @@ impl LiveCli {
         Ok(())
     }
 
+    fn run_init() -> Result<(), Box<dyn std::error::Error>> {
+        println!("{}", init_claude_md()?);
+        Ok(())
+    }
+
     fn print_diff() -> Result<(), Box<dyn std::error::Error>> {
         println!("{}", render_diff_report()?);
         Ok(())
@@ -1702,12 +1721,67 @@ fn render_memory_report() -> Result<String, Box<dyn std::error::Error>> {
 
 fn init_claude_md() -> Result<String, Box<dyn std::error::Error>> {
     let cwd = env::current_dir()?;
-    Ok(initialize_repo(&cwd)?.render())
+    let claude_md = cwd.join("CLAUDE.md");
+    if claude_md.exists() {
+        return Ok(format_init_report(&claude_md, false));
+    }
+
+    let content = render_init_claude_md(&cwd);
+    fs::write(&claude_md, content)?;
+    Ok(format_init_report(&claude_md, true))
 }
 
-fn run_init() -> Result<(), Box<dyn std::error::Error>> {
-    println!("{}", init_claude_md()?);
-    Ok(())
+fn render_init_claude_md(cwd: &Path) -> String {
+    let mut lines = vec![
+        "# CLAUDE.md".to_string(),
+        String::new(),
+        "This file provides guidance to Claude Code (claude.ai/code) when working with code in this repository.".to_string(),
+        String::new(),
+    ];
+
+    let mut command_lines = Vec::new();
+    if cwd.join("rust").join("Cargo.toml").is_file() {
+        command_lines.push("- Run Rust verification from `rust/`: `cargo fmt`, `cargo clippy --workspace --all-targets -- -D warnings`, `cargo test --workspace`".to_string());
+    } else if cwd.join("Cargo.toml").is_file() {
+        command_lines.push("- Run Rust verification from the repo root: `cargo fmt`, `cargo clippy --workspace --all-targets -- -D warnings`, `cargo test --workspace`".to_string());
+    }
+    if cwd.join("tests").is_dir() && cwd.join("src").is_dir() {
+        command_lines.push("- `src/` and `tests/` are also present; check those surfaces before removing or renaming Python-era compatibility assets.".to_string());
+    }
+    if !command_lines.is_empty() {
+        lines.push("## Verification".to_string());
+        lines.extend(command_lines);
+        lines.push(String::new());
+    }
+
+    let mut structure_lines = Vec::new();
+    if cwd.join("rust").is_dir() {
+        structure_lines.push(
+            "- `rust/` contains the Rust workspace and the active CLI/runtime implementation."
+                .to_string(),
+        );
+    }
+    if cwd.join("src").is_dir() {
+        structure_lines.push("- `src/` contains the older Python-first workspace artifacts referenced by the repo history and tests.".to_string());
+    }
+    if cwd.join("tests").is_dir() {
+        structure_lines.push("- `tests/` exercises compatibility and porting behavior across the repository surfaces.".to_string());
+    }
+    if !structure_lines.is_empty() {
+        lines.push("## Repository shape".to_string());
+        lines.extend(structure_lines);
+        lines.push(String::new());
+    }
+
+    lines.push("## Working agreement".to_string());
+    lines.push("- Prefer small, reviewable Rust changes and keep slash-command behavior aligned between the shared command registry and the CLI entrypoints.".to_string());
+    lines.push("- Do not overwrite existing CLAUDE.md content automatically; update it intentionally when repo workflows change.".to_string());
+    lines.push(String::new());
+
+    lines.join(
+        "
+",
+    )
 }
 
 fn normalize_permission_mode(mode: &str) -> Option<&'static str> {
@@ -1946,7 +2020,7 @@ impl ApiClient for AnthropicRuntimeClient {
         let message_request = MessageRequest {
             model: self.model.clone(),
             max_tokens: DEFAULT_MAX_TOKENS,
-            messages: convert_messages(&request.messages),
+            messages: convert_messages(&request.messages)?,
             system: (!request.system_prompt.is_empty()).then(|| request.system_prompt.join("\n\n")),
             tools: self.enable_tools.then(|| {
                 filter_tool_specs(self.allowed_tools.as_ref())
@@ -2225,7 +2299,10 @@ fn tool_permission_specs() -> Vec<ToolSpec> {
     mvp_tool_specs()
 }
 
-fn convert_messages(messages: &[ConversationMessage]) -> Vec<InputMessage> {
+fn convert_messages(messages: &[ConversationMessage]) -> Result<Vec<InputMessage>, RuntimeError> {
+    let cwd = env::current_dir().map_err(|error| {
+        RuntimeError::new(format!("failed to resolve current directory: {error}"))
+    })?;
     messages
         .iter()
         .filter_map(|message| {
@@ -2236,95 +2313,252 @@ fn convert_messages(messages: &[ConversationMessage]) -> Vec<InputMessage> {
             let content = message
                 .blocks
                 .iter()
-                .map(|block| match block {
-                    ContentBlock::Text { text } => InputContentBlock::Text { text: text.clone() },
-                    ContentBlock::ToolUse { id, name, input } => InputContentBlock::ToolUse {
-                        id: id.clone(),
-                        name: name.clone(),
-                        input: serde_json::from_str(input)
-                            .unwrap_or_else(|_| serde_json::json!({ "raw": input })),
-                    },
-                    ContentBlock::ToolResult {
-                        tool_use_id,
-                        output,
-                        is_error,
-                        ..
-                    } => InputContentBlock::ToolResult {
-                        tool_use_id: tool_use_id.clone(),
-                        content: vec![ToolResultContentBlock::Text {
-                            text: output.clone(),
-                        }],
-                        is_error: *is_error,
-                    },
-                })
-                .collect::<Vec<_>>();
-            (!content.is_empty()).then(|| InputMessage {
-                role: role.to_string(),
-                content,
-            })
+                .try_fold(Vec::new(), |mut acc, block| {
+                    match block {
+                        ContentBlock::Text { text } => {
+                            if message.role == MessageRole::User {
+                                acc.extend(
+                                    prompt_to_content_blocks(text, &cwd)
+                                        .map_err(RuntimeError::new)?,
+                                );
+                            } else {
+                                acc.push(InputContentBlock::Text { text: text.clone() });
+                            }
+                        }
+                        ContentBlock::ToolUse { id, name, input } => {
+                            acc.push(InputContentBlock::ToolUse {
+                                id: id.clone(),
+                                name: name.clone(),
+                                input: serde_json::from_str(input)
+                                    .unwrap_or_else(|_| serde_json::json!({ "raw": input })),
+                            });
+                        }
+                        ContentBlock::ToolResult {
+                            tool_use_id,
+                            output,
+                            is_error,
+                            ..
+                        } => acc.push(InputContentBlock::ToolResult {
+                            tool_use_id: tool_use_id.clone(),
+                            content: vec![ToolResultContentBlock::Text {
+                                text: output.clone(),
+                            }],
+                            is_error: *is_error,
+                        }),
+                    }
+                    Ok::<_, RuntimeError>(acc)
+                });
+            match content {
+                Ok(content) if !content.is_empty() => Some(Ok(InputMessage {
+                    role: role.to_string(),
+                    content,
+                })),
+                Ok(_) => None,
+                Err(error) => Some(Err(error)),
+            }
         })
         .collect()
 }
 
-fn print_help_to(out: &mut impl Write) -> io::Result<()> {
-    writeln!(out, "rusty-claude-cli v{VERSION}")?;
-    writeln!(out)?;
-    writeln!(out, "Usage:")?;
-    writeln!(
-        out,
-        "  rusty-claude-cli [--model MODEL] [--allowedTools TOOL[,TOOL...]]"
-    )?;
-    writeln!(out, "      Start the interactive REPL")?;
-    writeln!(
-        out,
-        "  rusty-claude-cli [--model MODEL] [--output-format text|json] prompt TEXT"
-    )?;
-    writeln!(out, "      Send one prompt and exit")?;
-    writeln!(
-        out,
-        "  rusty-claude-cli [--model MODEL] [--output-format text|json] TEXT"
-    )?;
-    writeln!(out, "      Shorthand non-interactive prompt mode")?;
-    writeln!(
-        out,
-        "  rusty-claude-cli --resume SESSION.json [/status] [/compact] [...]"
-    )?;
-    writeln!(
-        out,
-        "      Inspect or maintain a saved session without entering the REPL"
-    )?;
-    writeln!(out, "  rusty-claude-cli dump-manifests")?;
-    writeln!(out, "  rusty-claude-cli bootstrap-plan")?;
-    writeln!(
-        out,
-        "  rusty-claude-cli system-prompt [--cwd PATH] [--date YYYY-MM-DD]"
-    )?;
-    writeln!(out, "  rusty-claude-cli login")?;
-    writeln!(out, "  rusty-claude-cli logout")?;
-    writeln!(out, "  rusty-claude-cli init")?;
-    writeln!(out)?;
-    writeln!(out, "Flags:")?;
-    writeln!(
-        out,
-        "  --model MODEL              Override the active model"
-    )?;
-    writeln!(
-        out,
-        "  --output-format FORMAT     Non-interactive output format: text or json"
-    )?;
-    writeln!(
-        out,
-        "  --permission-mode MODE     Set read-only, workspace-write, or danger-full-access"
-    )?;
-    writeln!(out, "  --allowedTools TOOLS       Restrict enabled tools (repeatable; comma-separated aliases supported)")?;
-    writeln!(
-        out,
-        "  --version, -V              Print version and build information locally"
-    )?;
-    writeln!(out)?;
-    writeln!(out, "Interactive slash commands:")?;
-    writeln!(out, "{}", render_slash_command_help())?;
-    writeln!(out)?;
+fn prompt_to_content_blocks(input: &str, cwd: &Path) -> Result<Vec<InputContentBlock>, String> {
+    let mut blocks = Vec::new();
+    let mut text_buffer = String::new();
+    let mut chars = input.char_indices().peekable();
+
+    while let Some((index, ch)) = chars.next() {
+        if ch == '!' && input[index..].starts_with("![") {
+            if let Some((alt_end, path_start, path_end)) = parse_markdown_image_ref(input, index) {
+                let _ = alt_end;
+                flush_text_block(&mut blocks, &mut text_buffer);
+                let path = &input[path_start..path_end];
+                blocks.push(load_image_block(path, cwd)?);
+                while let Some((next_index, _)) = chars.peek() {
+                    if *next_index < path_end + 1 {
+                        let _ = chars.next();
+                    } else {
+                        break;
+                    }
+                }
+                continue;
+            }
+        }
+
+        if ch == '@' && is_ref_boundary(input[..index].chars().next_back()) {
+            let path_end = find_path_end(input, index + 1);
+            if path_end > index + 1 {
+                let candidate = &input[index + 1..path_end];
+                if looks_like_image_ref(candidate, cwd) {
+                    flush_text_block(&mut blocks, &mut text_buffer);
+                    blocks.push(load_image_block(candidate, cwd)?);
+                    while let Some((next_index, _)) = chars.peek() {
+                        if *next_index < path_end {
+                            let _ = chars.next();
+                        } else {
+                            break;
+                        }
+                    }
+                    continue;
+                }
+            }
+        }
+
+        text_buffer.push(ch);
+    }
+
+    flush_text_block(&mut blocks, &mut text_buffer);
+    if blocks.is_empty() {
+        blocks.push(InputContentBlock::Text {
+            text: input.to_string(),
+        });
+    }
+    Ok(blocks)
+}
+
+fn parse_markdown_image_ref(input: &str, start: usize) -> Option<(usize, usize, usize)> {
+    let after_bang = input.get(start + 2..)?;
+    let alt_end_offset = after_bang.find("](")?;
+    let path_start = start + 2 + alt_end_offset + 2;
+    let remainder = input.get(path_start..)?;
+    let path_end_offset = remainder.find(')')?;
+    let path_end = path_start + path_end_offset;
+    Some((start + 2 + alt_end_offset, path_start, path_end))
+}
+
+fn is_ref_boundary(ch: Option<char>) -> bool {
+    ch.is_none_or(char::is_whitespace)
+}
+
+fn find_path_end(input: &str, start: usize) -> usize {
+    input[start..]
+        .char_indices()
+        .find_map(|(offset, ch)| (ch.is_whitespace()).then_some(start + offset))
+        .unwrap_or(input.len())
+}
+
+fn looks_like_image_ref(candidate: &str, cwd: &Path) -> bool {
+    let resolved = resolve_prompt_path(candidate, cwd);
+    media_type_for_path(Path::new(candidate)).is_some()
+        || resolved.is_file()
+        || candidate.contains(std::path::MAIN_SEPARATOR)
+        || candidate.starts_with("./")
+        || candidate.starts_with("../")
+}
+
+fn flush_text_block(blocks: &mut Vec<InputContentBlock>, text_buffer: &mut String) {
+    if text_buffer.is_empty() {
+        return;
+    }
+    blocks.push(InputContentBlock::Text {
+        text: std::mem::take(text_buffer),
+    });
+}
+
+fn load_image_block(path_ref: &str, cwd: &Path) -> Result<InputContentBlock, String> {
+    let resolved = resolve_prompt_path(path_ref, cwd);
+    let media_type = media_type_for_path(&resolved).ok_or_else(|| {
+        format!(
+            "unsupported image format for reference {IMAGE_REF_PREFIX}{path_ref}; supported: png, jpg, jpeg, gif, webp"
+        )
+    })?;
+    let bytes = fs::read(&resolved).map_err(|error| {
+        format!(
+            "failed to read image reference {}: {error}",
+            resolved.display()
+        )
+    })?;
+    Ok(InputContentBlock::Image {
+        source: ImageSource {
+            kind: "base64".to_string(),
+            media_type: media_type.to_string(),
+            data: encode_base64(&bytes),
+        },
+    })
+}
+
+fn resolve_prompt_path(path_ref: &str, cwd: &Path) -> PathBuf {
+    let path = Path::new(path_ref);
+    if path.is_absolute() {
+        path.to_path_buf()
+    } else {
+        cwd.join(path)
+    }
+}
+
+fn media_type_for_path(path: &Path) -> Option<&'static str> {
+    let extension = path.extension()?.to_str()?.to_ascii_lowercase();
+    match extension.as_str() {
+        "png" => Some("image/png"),
+        "jpg" | "jpeg" => Some("image/jpeg"),
+        "gif" => Some("image/gif"),
+        "webp" => Some("image/webp"),
+        _ => None,
+    }
+}
+
+fn encode_base64(bytes: &[u8]) -> String {
+    const TABLE: &[u8; 64] = b"ABCDEFGHIJKLMNOPQRSTUVWXYZabcdefghijklmnopqrstuvwxyz0123456789+/";
+    let mut output = String::new();
+    let mut index = 0;
+    while index + 3 <= bytes.len() {
+        let block = (u32::from(bytes[index]) << 16)
+            | (u32::from(bytes[index + 1]) << 8)
+            | u32::from(bytes[index + 2]);
+        output.push(TABLE[((block >> 18) & 0x3F) as usize] as char);
+        output.push(TABLE[((block >> 12) & 0x3F) as usize] as char);
+        output.push(TABLE[((block >> 6) & 0x3F) as usize] as char);
+        output.push(TABLE[(block & 0x3F) as usize] as char);
+        index += 3;
+    }
+
+    match bytes.len().saturating_sub(index) {
+        1 => {
+            let block = u32::from(bytes[index]) << 16;
+            output.push(TABLE[((block >> 18) & 0x3F) as usize] as char);
+            output.push(TABLE[((block >> 12) & 0x3F) as usize] as char);
+            output.push('=');
+            output.push('=');
+        }
+        2 => {
+            let block = (u32::from(bytes[index]) << 16) | (u32::from(bytes[index + 1]) << 8);
+            output.push(TABLE[((block >> 18) & 0x3F) as usize] as char);
+            output.push(TABLE[((block >> 12) & 0x3F) as usize] as char);
+            output.push(TABLE[((block >> 6) & 0x3F) as usize] as char);
+            output.push('=');
+        }
+        _ => {}
+    }
+
+    output
+}
+
+fn print_help() {
+    println!("rusty-claude-cli v{VERSION}");
+    println!();
+    println!("Usage:");
+    println!("  rusty-claude-cli [--model MODEL] [--allowedTools TOOL[,TOOL...]]");
+    println!("      Start the interactive REPL");
+    println!("  rusty-claude-cli [--model MODEL] [--output-format text|json] prompt TEXT");
+    println!("      Send one prompt and exit");
+    println!("  rusty-claude-cli [--model MODEL] [--output-format text|json] TEXT");
+    println!("      Shorthand non-interactive prompt mode");
+    println!("  rusty-claude-cli --resume SESSION.json [/status] [/compact] [...]");
+    println!("      Inspect or maintain a saved session without entering the REPL");
+    println!("  rusty-claude-cli dump-manifests");
+    println!("  rusty-claude-cli bootstrap-plan");
+    println!("  rusty-claude-cli system-prompt [--cwd PATH] [--date YYYY-MM-DD]");
+    println!("  rusty-claude-cli login");
+    println!("  rusty-claude-cli logout");
+    println!();
+    println!("Flags:");
+    println!("  --model MODEL              Override the active model");
+    println!("  --output-format FORMAT     Non-interactive output format: text or json");
+    println!("  --permission-mode MODE     Set read-only, workspace-write, or danger-full-access");
+    println!("  --allowedTools TOOLS       Restrict enabled tools (repeatable; comma-separated aliases supported)");
+    println!("  --version, -V              Print version and build information locally");
+    println!();
+    println!("Interactive slash commands:");
+    println!("{}", render_slash_command_help());
+    println!();
     let resume_commands = resume_supported_slash_commands()
         .into_iter()
         .map(|spec| match spec.argument_hint {
@@ -2333,46 +2567,30 @@ fn print_help_to(out: &mut impl Write) -> io::Result<()> {
         })
         .collect::<Vec<_>>()
         .join(", ");
-    writeln!(out, "Resume-safe commands: {resume_commands}")?;
-    writeln!(out, "Examples:")?;
-    writeln!(
-        out,
-        "  rusty-claude-cli --model claude-opus \"summarize this repo\""
-    )?;
-    writeln!(
-        out,
-        "  rusty-claude-cli --output-format json prompt \"explain src/main.rs\""
-    )?;
-    writeln!(
-        out,
-        "  rusty-claude-cli --allowedTools read,glob \"summarize Cargo.toml\""
-    )?;
-    writeln!(
-        out,
-        "  rusty-claude-cli --resume session.json /status /diff /export notes.txt"
-    )?;
-    writeln!(out, "  rusty-claude-cli login")?;
-    writeln!(out, "  rusty-claude-cli init")?;
-    Ok(())
-}
-
-fn print_help() {
-    let _ = print_help_to(&mut io::stdout());
+    println!("Resume-safe commands: {resume_commands}");
+    println!("Examples:");
+    println!("  rusty-claude-cli --model claude-opus \"summarize this repo\"");
+    println!("  rusty-claude-cli --output-format json prompt \"explain src/main.rs\"");
+    println!("  rusty-claude-cli --allowedTools read,glob \"summarize Cargo.toml\"");
+    println!("  rusty-claude-cli --resume session.json /status /diff /export notes.txt");
+    println!("  rusty-claude-cli login");
 }
 
 #[cfg(test)]
 mod tests {
     use super::{
-        filter_tool_specs, format_compact_report, format_cost_report, format_model_report,
-        format_model_switch_report, format_permissions_report, format_permissions_switch_report,
-        format_resume_report, format_status_report, format_tool_call_start, format_tool_result,
-        normalize_permission_mode, parse_args, parse_git_status_metadata, print_help_to,
-        render_config_report, render_memory_report, render_repl_help,
-        resume_supported_slash_commands, status_context, CliAction, CliOutputFormat, SlashCommand,
-        StatusUsage, DEFAULT_MODEL,
+        filter_tool_specs, format_compact_report, format_cost_report, format_init_report,
+        format_model_report, format_model_switch_report, format_permissions_report,
+        format_permissions_switch_report, format_resume_report, format_status_report,
+        format_tool_call_start, format_tool_result, normalize_permission_mode, parse_args,
+        parse_git_status_metadata, render_config_report, render_init_claude_md,
+        render_memory_report, render_repl_help, resume_supported_slash_commands, status_context,
+        CliAction, CliOutputFormat, SlashCommand, StatusUsage, DEFAULT_MODEL,
     };
+    use api::InputContentBlock;
     use runtime::{ContentBlock, ConversationMessage, MessageRole, PermissionMode};
-    use std::path::PathBuf;
+    use std::path::{Path, PathBuf};
+    use std::time::{SystemTime, UNIX_EPOCH};
 
     #[test]
     fn defaults_to_repl_when_no_args() {
@@ -2508,10 +2726,6 @@ mod tests {
             parse_args(&["logout".to_string()]).expect("logout should parse"),
             CliAction::Logout
         );
-        assert_eq!(
-            parse_args(&["init".to_string()]).expect("init should parse"),
-            CliAction::Init
-        );
     }
 
     #[test]
@@ -2666,11 +2880,12 @@ mod tests {
     }
 
     #[test]
-    fn init_help_mentions_direct_subcommand() {
-        let mut help = Vec::new();
-        print_help_to(&mut help).expect("help should render");
-        let help = String::from_utf8(help).expect("help should be utf8");
-        assert!(help.contains("rusty-claude-cli init"));
+    fn init_report_uses_structured_output() {
+        let created = format_init_report(Path::new("/tmp/CLAUDE.md"), true);
+        assert!(created.contains("Init"));
+        assert!(created.contains("Result           created"));
+        let skipped = format_init_report(Path::new("/tmp/CLAUDE.md"), false);
+        assert!(skipped.contains("skipped (already exists)"));
     }
 
     #[test]
@@ -2774,7 +2989,7 @@ mod tests {
     fn status_context_reads_real_workspace_metadata() {
         let context = status_context(None).expect("status context should load");
         assert!(context.cwd.is_absolute());
-        assert_eq!(context.discovered_config_files, 5);
+        assert!(context.discovered_config_files >= 3);
         assert!(context.loaded_config_files <= context.discovered_config_files);
     }
 
@@ -2832,7 +3047,7 @@ mod tests {
 
     #[test]
     fn init_template_mentions_detected_rust_workspace() {
-        let rendered = crate::init::render_init_claude_md(std::path::Path::new("."));
+        let rendered = render_init_claude_md(Path::new("."));
         assert!(rendered.contains("# CLAUDE.md"));
         assert!(rendered.contains("cargo clippy --workspace --all-targets -- -D warnings"));
     }
@@ -2858,11 +3073,110 @@ mod tests {
             },
         ];
 
-        let converted = super::convert_messages(&messages);
+        let converted = super::convert_messages(&messages).expect("messages should convert");
         assert_eq!(converted.len(), 3);
         assert_eq!(converted[1].role, "assistant");
         assert_eq!(converted[2].role, "user");
     }
+
+    #[test]
+    fn prompt_to_content_blocks_keeps_text_only_prompt() {
+        let blocks = super::prompt_to_content_blocks("hello world", Path::new("."))
+            .expect("text prompt should parse");
+        assert_eq!(
+            blocks,
+            vec![InputContentBlock::Text {
+                text: "hello world".to_string()
+            }]
+        );
+    }
+
+    #[test]
+    fn prompt_to_content_blocks_embeds_at_image_refs() {
+        let temp = temp_fixture_dir("at-image-ref");
+        let image_path = temp.join("sample.png");
+        std::fs::write(&image_path, [1_u8, 2, 3]).expect("fixture write");
+        let prompt = format!("describe @{} please", image_path.display());
+
+        let blocks = super::prompt_to_content_blocks(&prompt, Path::new("."))
+            .expect("image ref should parse");
+
+        assert!(matches!(
+            &blocks[0],
+            InputContentBlock::Text { text } if text == "describe "
+        ));
+        assert!(matches!(
+            &blocks[1],
+            InputContentBlock::Image { source }
+                if source.kind == "base64"
+                    && source.media_type == "image/png"
+                    && source.data == "AQID"
+        ));
+        assert!(matches!(
+            &blocks[2],
+            InputContentBlock::Text { text } if text == " please"
+        ));
+    }
+
+    #[test]
+    fn prompt_to_content_blocks_embeds_markdown_image_refs() {
+        let temp = temp_fixture_dir("markdown-image-ref");
+        let image_path = temp.join("sample.webp");
+        std::fs::write(&image_path, [255_u8]).expect("fixture write");
+        let prompt = format!("see ![asset]({}) now", image_path.display());
+
+        let blocks = super::prompt_to_content_blocks(&prompt, Path::new("."))
+            .expect("markdown image ref should parse");
+
+        assert!(matches!(
+            &blocks[1],
+            InputContentBlock::Image { source }
+                if source.media_type == "image/webp" && source.data == "/w=="
+        ));
+    }
+
+    #[test]
+    fn prompt_to_content_blocks_rejects_unsupported_formats() {
+        let temp = temp_fixture_dir("unsupported-image-ref");
+        let image_path = temp.join("sample.bmp");
+        std::fs::write(&image_path, [1_u8]).expect("fixture write");
+        let prompt = format!("describe @{}", image_path.display());
+
+        let error = super::prompt_to_content_blocks(&prompt, Path::new("."))
+            .expect_err("unsupported image ref should fail");
+
+        assert!(error.contains("unsupported image format"));
+    }
+
+    #[test]
+    fn convert_messages_expands_user_text_image_refs() {
+        let temp = temp_fixture_dir("convert-message-image-ref");
+        let image_path = temp.join("sample.gif");
+        std::fs::write(&image_path, [71_u8, 73, 70]).expect("fixture write");
+        let messages = vec![ConversationMessage::user_text(format!(
+            "inspect @{}",
+            image_path.display()
+        ))];
+
+        let converted = super::convert_messages(&messages).expect("messages should convert");
+
+        assert_eq!(converted.len(), 1);
+        assert!(matches!(
+            &converted[0].content[1],
+            InputContentBlock::Image { source }
+                if source.media_type == "image/gif" && source.data == "R0lG"
+        ));
+    }
+
+    fn temp_fixture_dir(label: &str) -> PathBuf {
+        let unique = SystemTime::now()
+            .duration_since(UNIX_EPOCH)
+            .expect("clock should advance")
+            .as_nanos();
+        let path = std::env::temp_dir().join(format!("rusty-claude-cli-{label}-{unique}"));
+        std::fs::create_dir_all(&path).expect("temp dir should exist");
+        path
+    }
     #[test]
     fn repl_help_mentions_history_completion_and_multiline() {
         let help = render_repl_help();