Add better options for dropped or pasted files.

Dropping into ssh will now offer to upload and paste path, making it easy to send claude code images on remote hosts.

You can also copy raw image data and paste it, and it'll give you b64, make file and paste path, or upload options, depending on whether you're sshed.

Author: gnachman

CLAUDE.md

@@ -13,3 +13,5 @@
 - The deployment target for iTerm2 is macOS 12. You don't need to perform availability checks for older versions.
 - Don't replace curly quotes with straight quotes. Same for apostrophes and single quotes.
 - In user-visible strings do not use " except as a shorthand for inch. Prefer curly quotes like “ and ”. I know this goes against your nature, but fight hard here.
+- Never use auto layout in the terminal window. It virally spreads and breaks autoresizing. It is fine to use it in other windows without a lot of existing autoresizing mask-based code (e.g., the AI chat window)
+- The deployment target is macOS 12. Don't add availability checks for 12 and lower.

ThirdParty/UKCrashReporter/UKCrashReporter.m

@@ -98,8 +98,6 @@ void    UKCrashReporterCheckForCrash(void)
                 NSTimeInterval    lastCrashReportInterval = [[NSUserDefaults standardUserDefaults] floatForKey: @"UKCrashReporterLastCrashReportDate"];
                 NSDate*            lastTimeCrashReported = [NSDate dateWithTimeIntervalSince1970: lastCrashReportInterval];
 
-                NSUserDefaults *d = [NSUserDefaults standardUserDefaults];
-
                 NSString *errorLog = nil;
                 @try {
                     errorLog = UKReadErrorLog();

iTerm2.xcodeproj/project.pbxproj

@@ -10,6 +10,7 @@
 		02BBB9199A50961FFEAC2D6D /* iTermFindOnPageHelperTests.swift in Sources */ = {isa = PBXBuildFile; fileRef = 98E9463133DCF8311E0E5B6E /* iTermFindOnPageHelperTests.swift */; };
 		052FA2457F95F63A46C30503 /* IntervalTreeCoordinateClampingTests.swift in Sources */ = {isa = PBXBuildFile; fileRef = F6601DD02DFE3C2480DFDC73 /* IntervalTreeCoordinateClampingTests.swift */; };
 		06E0C88E1DF9695400AA061B /* iTermServiceProvider.h in Headers */ = {isa = PBXBuildFile; fileRef = 06E0C88C1DF9695400AA061B /* iTermServiceProvider.h */; };
+		084F626684E68821BAEC7D9B /* iTermNonTextPasteHelper.swift in Sources */ = {isa = PBXBuildFile; fileRef = ED49EE365D629DAE80503BFD /* iTermNonTextPasteHelper.swift */; };
 		10AAA7668EA8FBDD64696AB7 /* iTermEventTriggerParameterView.swift in Sources */ = {isa = PBXBuildFile; fileRef = DE7B0AE10E1598EDE1E01795 /* iTermEventTriggerParameterView.swift */; };
 		1D027C111CD1867000B0FBFF /* iTermColorPresets.h in Headers */ = {isa = PBXBuildFile; fileRef = 1D027C0F1CD1867000B0FBFF /* iTermColorPresets.h */; };
 		1D0318281A42563A00932107 /* iTermImageWell.h in Headers */ = {isa = PBXBuildFile; fileRef = 1D0318261A42563A00932107 /* iTermImageWell.h */; };
@@ -944,6 +945,7 @@
 		874206530564169600CFC3F1 /* AppKit.framework in Frameworks */ = {isa = PBXBuildFile; fileRef = 0464AB2F006CD2EC7F000001 /* AppKit.framework */; };
 		90A1E13B186F9EA4003EC3E8 /* AppleScriptTest.m in Sources */ = {isa = PBXBuildFile; fileRef = 90A1E13A186F9EA4003EC3E8 /* AppleScriptTest.m */; };
 		98063D9BFF61AB290BEE435C /* iTermCursorSlideAnimator.m in Sources */ = {isa = PBXBuildFile; fileRef = 479FDFE9C0F424FEC10526EC /* iTermCursorSlideAnimator.m */; };
+		9C2DA778D246D42A1DC362CC /* iTermUploadIndicator.swift in Sources */ = {isa = PBXBuildFile; fileRef = 698B6ED16A3CD11D402C364B /* iTermUploadIndicator.swift */; };
 		9D737D5F17495B4100B3334D /* PrefsGeneral.png in Resources */ = {isa = PBXBuildFile; fileRef = 9D737D5D17495B4100B3334D /* PrefsGeneral.png */; };
 		9D737D6017495B4100B3334D /* PrefsGeneral@2x.png in Resources */ = {isa = PBXBuildFile; fileRef = 9D737D5E17495B4100B3334D /* PrefsGeneral@2x.png */; };
 		9DB3D6E0176C8F0B0071CCF8 /* PrefsAppearance.png in Resources */ = {isa = PBXBuildFile; fileRef = 9DB3D6DE176C8F0B0071CCF8 /* PrefsAppearance.png */; };
@@ -6201,6 +6203,7 @@
 		53FF984A20967805008688D7 /* iTermMetalDeviceProvider.m */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.c.objc; path = iTermMetalDeviceProvider.m; sourceTree = "<group>"; };
 		5ECE005D1454E59B004861E9 /* PseudoTerminalRestorer.h */ = {isa = PBXFileReference; fileEncoding = 4; indentWidth = 4; lastKnownFileType = sourcecode.c.h; path = PseudoTerminalRestorer.h; sourceTree = "<group>"; tabWidth = 4; };
 		5ECE005E1454E59B004861E9 /* PseudoTerminalRestorer.m */ = {isa = PBXFileReference; fileEncoding = 4; indentWidth = 4; lastKnownFileType = sourcecode.c.objc; path = PseudoTerminalRestorer.m; sourceTree = "<group>"; tabWidth = 4; };
+		698B6ED16A3CD11D402C364B /* iTermUploadIndicator.swift */ = {isa = PBXFileReference; includeInIndex = 1; lastKnownFileType = sourcecode.swift; path = iTermUploadIndicator.swift; sourceTree = "<group>"; };
 		756C32AB2597AC2E0047B3A9 /* iTermImage+Sixel.h */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.c.h; path = "iTermImage+Sixel.h"; sourceTree = "<group>"; };
 		756C32AC2597AC2E0047B3A9 /* iTermImage+Sixel.m */ = {isa = PBXFileReference; lastKnownFileType = sourcecode.c.objc; path = "iTermImage+Sixel.m"; sourceTree = "<group>"; };
 		756C32C12597AC9C0047B3A9 /* libaprutil-1.tbd */ = {isa = PBXFileReference; lastKnownFileType = "sourcecode.text-based-dylib-definition"; name = "libaprutil-1.tbd"; path = "Platforms/MacOSX.platform/Developer/SDKs/MacOSX.sdk/usr/lib/libaprutil-1.tbd"; sourceTree = DEVELOPER_DIR; };
@@ -9148,6 +9151,7 @@
 		E8CF7563026DDA6303A80106 /* VT100Terminal.m */ = {isa = PBXFileReference; fileEncoding = 4; indentWidth = 4; lastKnownFileType = sourcecode.c.objc; path = VT100Terminal.m; sourceTree = "<group>"; tabWidth = 4; };
 		E8CF757F026DDAD703A80106 /* main.m */ = {isa = PBXFileReference; fileEncoding = 30; indentWidth = 4; lastKnownFileType = sourcecode.c.objc; path = main.m; sourceTree = "<group>"; tabWidth = 4; };
 		E8E901A202743CA303A80106 /* NSStringITerm.m */ = {isa = PBXFileReference; fileEncoding = 4; indentWidth = 4; lastKnownFileType = sourcecode.c.objc; path = NSStringITerm.m; sourceTree = "<group>"; tabWidth = 4; };
+		ED49EE365D629DAE80503BFD /* iTermNonTextPasteHelper.swift */ = {isa = PBXFileReference; includeInIndex = 1; lastKnownFileType = sourcecode.swift; path = iTermNonTextPasteHelper.swift; sourceTree = "<group>"; };
 		F52ED8DD037F0A7D01A8A066 /* PTYSession.m */ = {isa = PBXFileReference; fileEncoding = 4; indentWidth = 4; lastKnownFileType = sourcecode.c.objc; lineEnding = 0; path = PTYSession.m; sourceTree = "<group>"; tabWidth = 4; xcLanguageSpecificationIdentifier = xcode.lang.objc; };
 		F56B230B03A1B36701A8A066 /* PTYWindow.m */ = {isa = PBXFileReference; fileEncoding = 30; indentWidth = 4; lastKnownFileType = sourcecode.c.objc; lineEnding = 0; path = PTYWindow.m; sourceTree = "<group>"; tabWidth = 4; xcLanguageSpecificationIdentifier = xcode.lang.objc; };
 		F5E533B403B2959201A8A066 /* PTYTabView.m */ = {isa = PBXFileReference; fileEncoding = 30; indentWidth = 4; lastKnownFileType = sourcecode.c.objc; path = PTYTabView.m; sourceTree = "<group>"; tabWidth = 4; };
@@ -13396,6 +13400,8 @@
 				76421C2E762130B690D1ADC5 /* RegexAtomIterator.swift */,
 				889A9128E944B618CDE75E18 /* iTermCursorSlideAnimator.h */,
 				479FDFE9C0F424FEC10526EC /* iTermCursorSlideAnimator.m */,
+				ED49EE365D629DAE80503BFD /* iTermNonTextPasteHelper.swift */,
+				698B6ED16A3CD11D402C364B /* iTermUploadIndicator.swift */,
 			);
 			path = sources;
 			sourceTree = "<group>";
@@ -20005,6 +20011,8 @@
 				A785F516A64BC93AAF1474B8 /* RegexAtomIterator.swift in Sources */,
 				EE293B4DA9D2204FCFDE6784 /* iTermCursorSlideAnimator.h in Sources */,
 				98063D9BFF61AB290BEE435C /* iTermCursorSlideAnimator.m in Sources */,
+				084F626684E68821BAEC7D9B /* iTermNonTextPasteHelper.swift in Sources */,
+				9C2DA778D246D42A1DC362CC /* iTermUploadIndicator.swift in Sources */,
 			);
 			runOnlyForDeploymentPostprocessing = 0;
 		};

sources/Conductor.swift

@@ -1528,11 +1528,67 @@ extension Conductor {
     @available(macOS 11, *)
     @objc(uploadFile:to:)
     func upload(file: String, to destinationPath: SCPPath) {
-        let file = ConductorFileTransfer(path: destinationPath,
-                                         localPath: file,
-                                         data: nil,
-                                         delegate: self)
-        file.upload()
+        _ = upload(file: file, to: destinationPath, completion: { _, _ in })
+    }
+
+    @available(macOS 11, *)
+    @objc(uploadFile:to:withCompletion:)
+    func upload(file: String, to destinationPath: SCPPath, completion: @escaping (Bool, String?) -> Void) -> TransferrableFile? {
+        let localPath: String
+        let remotePath: SCPPath
+        let tempArchivePath: String?
+
+        // Check if it's a directory - create a tgz archive
+        var isDirectory: ObjCBool = false
+        if FileManager.default.fileExists(atPath: file, isDirectory: &isDirectory), isDirectory.boolValue {
+            do {
+                let result = try createArchiveForDirectory(file, destinationPath: destinationPath)
+                localPath = result.localPath
+                remotePath = result.remotePath
+                tempArchivePath = result.tempArchivePath
+            } catch {
+                DLog("Failed to create tgz archive: \(error)")
+                completion(false, error.localizedDescription)
+                return nil
+            }
+        } else {
+            localPath = file
+            remotePath = destinationPath
+            tempArchivePath = nil
+        }
+
+        let transfer = ConductorFileTransfer(path: remotePath,
+                                             localPath: localPath,
+                                             data: nil,
+                                             delegate: self)
+        transfer.completionBlock = { success, error in
+            // Clean up temp archive if we created one
+            if let tempPath = tempArchivePath {
+                try? FileManager.default.removeItem(atPath: tempPath)
+            }
+            completion(success, error)
+        }
+        transfer.upload()
+        return transfer
+    }
+
+    private struct DirectoryArchiveResult {
+        let localPath: String
+        let remotePath: SCPPath
+        let tempArchivePath: String
+    }
+
+    private func createArchiveForDirectory(_ directoryPath: String, destinationPath: SCPPath) throws -> DirectoryArchiveResult {
+        DLog("Converting directory to tgz for conductor upload: \(directoryPath)")
+
+        let tempPath = try NSData.temporaryTGZArchive(ofDirectory: directoryPath)
+
+        let remotePath = SCPPath()
+        remotePath.hostname = destinationPath.hostname
+        remotePath.username = destinationPath.username
+        remotePath.path = destinationPath.path + ".tgz"
+
+        return DirectoryArchiveResult(localPath: tempPath, remotePath: remotePath, tempArchivePath: tempPath)
     }
 
     private var jumpScript: String {

sources/FileTransferManager.m

@@ -343,6 +343,14 @@ - (void)transferrableFile:(TransferrableFile *)transferrableFile
 
     TransferrableFileMenuItemViewController *controller = [self viewControllerForTransferrableFile:transferrableFile];
     [controller update];
+
+    // Call the completion block if set
+    if (transferrableFile.completionBlock) {
+        BOOL success = (error == nil);
+        NSString *errorMessage = error.localizedDescription;
+        transferrableFile.completionBlock(success, errorMessage);
+        transferrableFile.completionBlock = nil;  // Clear to avoid retain cycles
+    }
 }
 
 - (void)transferrableFileWillStop:(TransferrableFile *)transferrableFile {
@@ -357,6 +365,12 @@ - (void)transferrableFileDidStopTransfer:(TransferrableFile *)transferrableFile
     transferrableFile.status = kTransferrableFileStatusCancelled;
     TransferrableFileMenuItemViewController *controller = [self viewControllerForTransferrableFile:transferrableFile];
     [controller update];
+
+    // Call the completion block if set (transfer was cancelled)
+    if (transferrableFile.completionBlock) {
+        transferrableFile.completionBlock(NO, @"Transfer cancelled");
+        transferrableFile.completionBlock = nil;
+    }
 }
 
 

sources/NSData+iTerm.h

@@ -27,6 +27,11 @@ NS_ASSUME_NONNULL_BEGIN
                             includeExtendedAttrs:(BOOL)includeExtendedAttrs
                                            error:(NSError * _Nullable __autoreleasing * _Nullable)error;
 
+// Creates a .tgz archive of the given directory and writes it to a temp file.
+// Returns the path to the temp file on success, or nil on failure.
++ (NSString * _Nullable)temporaryTGZArchiveOfDirectory:(NSString *)directoryPath
+                                                 error:(NSError * _Nullable __autoreleasing * _Nullable)error;
+
 // returns a string the the data base-64 encoded into 77-column lines divided by lineBreak.
 - (NSString *)stringWithBase64EncodingWithLineBreak:(NSString *)lineBreak;
 

sources/NSData+iTerm.m

@@ -152,6 +152,50 @@ + (NSData *)dataWithTGZContainingFiles:(NSArray<NSString *> *)files
     return data;
 }
 
++ (NSString *)temporaryTGZArchiveOfDirectory:(NSString *)directoryPath
+                                       error:(NSError **)error {
+    NSString *folderName = [directoryPath lastPathComponent];
+    NSString *parentPath = [directoryPath stringByDeletingLastPathComponent];
+
+    NSError *archiveError = nil;
+    NSData *archiveData = [NSData dataWithTGZContainingFiles:@[folderName]
+                                              relativeToPath:parentPath
+                                        includeExtendedAttrs:NO
+                                                       error:&archiveError];
+    // Note: archiveError may be set even on success (e.g., tar warnings to stderr).
+    // Only fail if we didn't get any data back.
+    if (!archiveData) {
+        DLog(@"Failed to create tgz archive: %@", archiveError);
+        if (error) {
+            *error = archiveError ?: [NSError errorWithDomain:@"com.googlecode.iterm2"
+                                                         code:-1
+                                                     userInfo:@{ NSLocalizedDescriptionKey: @"Failed to create archive of folder." }];
+        }
+        return nil;
+    }
+    if (archiveError) {
+        DLog(@"tgz archive created with warning: %@", archiveError);
+    }
+
+    // Write archive to temp file
+    NSString *tempDir = NSTemporaryDirectory();
+    NSString *archiveName = [folderName stringByAppendingString:@".tgz"];
+    NSString *tempPath = [tempDir stringByAppendingPathComponent:archiveName];
+
+    if (![archiveData writeToFile:tempPath atomically:YES]) {
+        DLog(@"Failed to write temp archive to %@", tempPath);
+        if (error) {
+            *error = [NSError errorWithDomain:@"com.googlecode.iterm2"
+                                         code:-1
+                                     userInfo:@{ NSLocalizedDescriptionKey: @"Failed to write temporary archive file." }];
+        }
+        return nil;
+    }
+    DLog(@"Created temp archive at %@ (%lu bytes)", tempPath, (unsigned long)archiveData.length);
+
+    return tempPath;
+}
+
 - (BOOL)containsAsciiCharacterInSet:(NSCharacterSet *)asciiSet {
     char flags[256];
     for (int i = 0; i < 256; i++) {

sources/NSPasteboard+iTerm.h

@@ -13,4 +13,13 @@
 - (NSArray *)filenamesOnPasteboardWithShellEscaping:(BOOL)escape forPaste:(BOOL)forPaste;
 - (NSData *)dataForFirstFile;
 
+// Check for raw image data (not from a file URL)
+- (BOOL)hasRawImageData;
+- (NSData *)rawImageData;
+- (NSString *)rawImageDataUTType;
+
+// Check for file URLs
+- (BOOL)hasFileURLs;
+- (NSArray<NSString *> *)filePaths;
+
 @end

sources/NSPasteboard+iTerm.m

@@ -7,8 +7,10 @@
 //
 
 #import "NSPasteboard+iTerm.h"
+#import "DebugLogging.h"
 #import "NSStringITerm.h"
 #import "iTermPreferences.h"
+#import <UniformTypeIdentifiers/UniformTypeIdentifiers.h>
 
 @implementation NSPasteboard (iTerm)
 
@@ -53,4 +55,68 @@ - (NSData *)dataForFirstFile {
     return nil;
 }
 
+// Returns the UTType identifier for available image data, or nil if none.
+// Only checks type availability - does not fetch or decode any data.
+- (NSString *)rawImageDataUTType {
+    // Don't report image data if we have file URLs - those take precedence
+    if ([self hasFileURLs]) {
+        return nil;
+    }
+    NSArray<NSString *> *imageTypeIdentifiers = @[
+        UTTypePNG.identifier,
+        UTTypeJPEG.identifier,
+        UTTypeTIFF.identifier,
+        UTTypeBMP.identifier,
+        UTTypeGIF.identifier,
+        UTTypeWebP.identifier,
+        UTTypeHEIC.identifier
+    ];
+    return [self availableTypeFromArray:imageTypeIdentifiers];
+}
+
+- (BOOL)hasRawImageData {
+    return [self rawImageDataUTType] != nil;
+}
+
+// Fetches the raw bytes for the available image type.
+// Only call this when you actually need the data.
+- (NSData *)rawImageData {
+    NSString *type = [self rawImageDataUTType];
+    if (!type) {
+        return nil;
+    }
+    return [self dataForType:type];
+}
+
+- (BOOL)hasFileURLs {
+    DLog(@"hasFileURLs: pasteboard types=%@", self.types);
+    NSString *bestType = [self availableTypeFromArray:@[ NSPasteboardTypeFileURL ]];
+    DLog(@"hasFileURLs: bestType=%@", bestType);
+    if (![bestType isEqualToString:NSPasteboardTypeFileURL]) {
+        DLog(@"hasFileURLs: no file URL type available");
+        return NO;
+    }
+    NSArray<NSURL *> *urls = [self readObjectsForClasses:@[ [NSURL class] ] options:0];
+    DLog(@"hasFileURLs: urls=%@", urls);
+    for (NSURL *url in urls) {
+        if (url.isFileURL) {
+            DLog(@"hasFileURLs: found file URL %@", url);
+            return YES;
+        }
+    }
+    DLog(@"hasFileURLs: no file URLs found");
+    return NO;
+}
+
+- (NSArray<NSString *> *)filePaths {
+    NSMutableArray<NSString *> *paths = [NSMutableArray array];
+    NSArray<NSURL *> *urls = [self readObjectsForClasses:@[ [NSURL class] ] options:0];
+    for (NSURL *url in urls) {
+        if (url.isFileURL && url.path) {
+            [paths addObject:url.path];
+        }
+    }
+    return paths;
+}
+
 @end

sources/PTYSession+Private.h

@@ -39,15 +39,16 @@
 @class iTermComposerManager;
 @class iTermConductor;
 @class AITermControllerObjC;
+@class iTermNonTextPasteHelper;
 
 @interface PTYSession () <
 iTermAutomaticProfileSwitcherDelegate,
 iTermBackgroundDrawingHelperDelegate,
 iTermBadgeLabelDelegate,
+iTermComposerManagerDelegate,
+iTermConductorDelegate,
 iTermCoprocessDelegate,
 iTermCopyModeHandlerDelegate,
-iTermConductorDelegate,
-iTermComposerManagerDelegate,
 iTermFilterDestination,
 iTermHotKeyNavigableSession,
 iTermImmutableColorMapDelegate,
@@ -58,20 +59,21 @@ iTermMetalGlueDelegate,
 iTermModernKeyMapperDelegate,
 iTermModifyOtherKeysMapperDelegate,
 iTermNaggingControllerDelegate,
+iTermNonTextPasteHelperDelegate,
 iTermObject,
 iTermPasteHelperDelegate,
 iTermPasteboardReporterDelegate,
+iTermSessionDirectoryTrackerDelegate,
 iTermSessionNameControllerDelegate,
 iTermSessionViewDelegate,
 iTermShortcutNavigationModeHandlerDelegate,
 iTermStandardKeyMapperDelegate,
 iTermStatusBarViewControllerDelegate,
 iTermTailFindControllerDelegate,
 iTermTermkeyKeyMapperDelegate,
-iTermTriggersDataSource,
 iTermTmuxControllerSession,
+iTermTriggersDataSource,
 iTermUpdateCadenceControllerDelegate,
-iTermSessionDirectoryTrackerDelegate,
 TriggerDelegate> {
     // Changes are made in the main thread to this and it periodically copied to the mutation thread.
     iTermExpect *_expect;
@@ -81,6 +83,8 @@ TriggerDelegate> {
     iTermComposerManager *_composerManager;
     iTermAppSwitchingPreventionDetector *_appSwitchingPreventionDetector;
     AITermControllerObjC *_aiterm;
+    iTermNonTextPasteHelper *_nonTextPasteHelper;
+    TransferrableFile *_uploadAndPasteTransfer;  // Current upload for "upload and paste path" feature
 }
 
 @property(nonatomic, retain) Interval *currentMarkOrNotePosition;