Unable to sign app bundle using Qt frameworks on OS X 10.10

Question

I am having trouble signing Qt Based application un OS X. I am using Qt 5.3.2.

I have read various information source that contain contradictory information.

Here is the content of my application bundle after I run the bin/macdeployqt Qt utility

SimpleHello.app/
    Contents/
        Info.plist
        PkgInfo
        Frameworks/
            QtCore.framework/
                Resources/
                Versions/
                    5/
                        QtCore
            QtGui.framework/  ... same as Qt core
            QtPrintSupport.framework/  ... same as Qt core
            QtWidgets.framework/  ... same as Qt core
        MacOS/
            SimpleHello
        PlugIns/ ... some plugins
        Resources/
            empty.lproj
            qt.conf

First:

I tried: http://successfulsoftware.net/2012/08/30/how-to-sign-your-mac-os-x-app-for-gatekeeper/

However, it seems that it is not valid anymore in OS X 10.10 Yosemite

Second:

I tried: Sign a Framework for OSX 10.9

I was able to sign the whole application without any error. However, when running spctl to verify the validity of the application, I get

spctl -a -vvvv SimpleHello.app
SimpleHello.app/: rejected
source=obsolete resource envelope
origin=Developer ID Application: MY CERTIFICATE

Additionally when verifying signature with codesign, I get this:

codesign --verify --deep --verbose=4 SimpleHello.app
--prepared:/My/Path/SimpleHello.app/Contents/Frameworks/QtCore.framework
--validated:/My/Path/SimpleHello.app/Contents/Frameworks/QtCore.framework
SimpleHello.app/: embedded framework contains modified or invalid version
In subcomponent: /My/Path/SimpleHello.app/Contents/Frameworks/QtCore.framework

Third:

Added the --no-strict option in codesign verification according to: Error when export archive

It fixes the issue with codesign verification but does not fix the spctl issue.

Forth:

I tried adding the --no-legacy-signing option when signing frameworks. However I get this error when verifying the bundle signature (both with codesign and spctl

codesign --verify --deep --verbose=4 SimpleHello.app
SimpleHello.app/: code has no resources but signature indicates they must be present

Fifth:

Modified the framework structure according to: http://qt-project.org/forums/viewthread/47768 and https://gist.github.com/kingcheez/6154462d7734e0c0f3a4

In this case I get this error when trying to sign frameworks

SimpleHello.app/Contents/Frameworks/QtCore.framework: unsealed contents present in the root directory of an embedded framework
SimpleHello.app/Contents/Frameworks/QtGui.framework: unsealed contents present in the root directory of an embedded framework
SimpleHello.app/Contents/Frameworks/QtPrintSupport.framework: unsealed contents present in the root directory of an embedded framework
SimpleHello.app/Contents/Frameworks/QtWidgets.framework: unsealed contents present in the root directory of an embedded framework

EDIT: It seems that the issue with the unsealed contents present in the root directory of an embedded framework was because one of the simlink was malformed. It was:

QtCore.framework.framework/Versions/Current -> 5/

Instead of

QtCore.framework.framework/Versions/Current -> 5

After this fix, I still get the same result as in Sixth though.

Sixth:

Added the --no-strict option when calling codesign for Frameworks. I was able to sign all frameworks except for one

SimpleHello.app//Contents/Frameworks/QtCore.framework: signed bundle with Mach-O thin (x86_64) [.]
SimpleHello.app//Contents/Frameworks/QtGui.framework: signed bundle with Mach-O thin (x86_64) [.]
SimpleHello.app//Contents/Frameworks/QtPrintSupport.framework: code object is not signed at all
In subcomponent: /My/Path/SimpleHello.app/Contents/Frameworks/QtPrintSupport.framework/Versions/Current/QtPrintSupport
SimpleHello.app//Contents/Frameworks/QtWidgets.framework: signed bundle with Mach-O thin (x86_64) [.]

Seventh:

I posted this question since I don't know what to look for anymore

Answer 1

After digging a bit more, I figured out what the issue in section seventh was: Some of the Qt Framework contain bad information in the Info.plist files (framework name ends with _debug)

I came out with this script that fixes all issues (there are still a few hardcoded values that could probably get processed with some improvement to the script)

#!/bin/bash
# Script name: deploy.sh

# Following environment variables must be defined:
# - QT_FRAMEWORK_PATH
# - QT_BIN_PATH
# - CERTIFICATE
# - FRAMEWORKS
# - BAD_FRAMEWORKS


# retrieve bundle name from first parameter
BUNDLE_NAME=$1

# Run QT tool to deploy
${QT_BIN_PATH}/macdeployqt $BUNDLE_NAME

# FIX ISSUE 6
# Please note that Qt5 frameworks have incorrect layout after SDK build, so this isn't just a problem with `macdeployqt` but whole framework assembly part.
# Present
#   QtCore.framework/
#       Contents/
#           Info.plist
#       QtCore    -> Versions/Current/QtCore
#       Versions/
#           Current -> 5
#           5/
#               QtCore
# After macdeployqt
#   QtCore.framework/
#       Resources/
#       Versions/
#           5/
#               QtCore
#
# Expected
#   QtCore.framework/
#       QtCore    -> Versions/Current/QtCore
#       Resources -> Versions/Current/Resources
#       Versions/
#           Current -> 5
#           5/
#               QtCore
#               Resources/
#                   Info.plist
# So in order to comply with expected layout: https://developer.apple.com/library/mac/documentation/MacOSX/Conceptual/BPFrameworks/Concepts/FrameworkAnatomy.html

for CURRENT_FRAMEWORK in ${FRAMEWORKS}; do
    echo "Processing framework: ${CURRENT_FRAMEWORK}"

    echo "Deleting existing resource folder"
    rmdir ${BUNDLE_NAME}/Contents/Frameworks/${CURRENT_FRAMEWORK}.framework/Resources

    echo "create resource folder"
    mkdir -p ${BUNDLE_NAME}/Contents/Frameworks/${CURRENT_FRAMEWORK}.framework/Versions/5/Resources

    echo "create copy resource file"
    cp ${QT_FRAMEWORK_PATH}/${CURRENT_FRAMEWORK}.framework/Contents/Info.plist $BUNDLE_NAME/Contents/Frameworks/${CURRENT_FRAMEWORK}.framework/Versions/5/Resources/

    echo "create symbolic links"
    ln -nfs 5                                     ${BUNDLE_NAME}/Contents/Frameworks/${CURRENT_FRAMEWORK}.framework/Versions/Current
    ln -nfs Versions/Current/${CURRENT_FRAMEWORK} ${BUNDLE_NAME}/Contents/Frameworks/${CURRENT_FRAMEWORK}.framework/${CURRENT_FRAMEWORK}
    ln -nfs Versions/Current/Resources            ${BUNDLE_NAME}/Contents/Frameworks/${CURRENT_FRAMEWORK}.framework/Resources
done

# FIX ISSUE 7
echo "***** Correct Frameworks Info.plist file*****"

for CURRENT_FRAMEWORK in ${BAD_FRAMEWORKS}; do
    echo "Correcting bad framework Info.plist: ${CURRENT_FRAMEWORK}"
    TMP=$(sed 's/_debug//g' ${BUNDLE_NAME}/Contents/Frameworks/${CURRENT_FRAMEWORK}.framework/Resources/Info.plist)
    echo "$TMP" > ${BUNDLE_NAME}/Contents/Frameworks/${CURRENT_FRAMEWORK}.framework/Resources/Info.plist
done

# SIGNING FIXED FRAMEWORK
CODESIGN_OPTIONS="--verbose=4"

#echo "******* Sign QtWebEngineProcess ***********"
#codesign --force --verify ${CODESIGN_OPTIONS} --sign "$CERTIFICATE" $BUNDLE_NAME/Contents/Frameworks/QtWebEngineCore.framework/Versions/Current/Helpers/QtWebEngineProcess.app
echo "******* Sign Frameworks-subApps ***********"
codesign --force --verify ${CODESIGN_OPTIONS} --sign "$CERTIFICATE" $BUNDLE_NAME/Contents/Frameworks/*.framework/Versions/*/*/*.app

echo "******* Signing Frameworks ***********"
for CURRENT_FRAMEWORK in ${FRAMEWORKS}; do
    echo "Signing framework: ${CURRENT_FRAMEWORK}"
    codesign --force --verify ${CODESIGN_OPTIONS} --sign "$CERTIFICATE" $BUNDLE_NAME/Contents/Frameworks/${CURRENT_FRAMEWORK}.framework
done

# Sign plugins
echo "******* Signing Plugins ***********"
codesign --force --verify ${CODESIGN_OPTIONS} --sign "${CERTIFICATE}" ${BUNDLE_NAME}/Contents/Plugins/*/*.dylib


# Sign bundle itself
echo "******* Signing Bundle ***********"
codesign --force --verify ${CODESIGN_OPTIONS} --sign "$CERTIFICATE" $BUNDLE_NAME

# Verify

echo "******* Verify Bundle ***********"
codesign --verify --deep ${CODESIGN_OPTIONS} $BUNDLE_NAME


echo "******* Verify Bundle using dpctl ***********"
spctl -a -vvvv $BUNDLE_NAME

As for calling the script:

# Define environment variables
export QT_FRAMEWORK_PATH=/Path/To/Qt_5.3.2/5.3/clang_64/lib
export QT_BIN_PATH=/Path/To/Qt_5.3.2/5.3/clang_64/bin
export CERTIFICATE="Developer ID Application: My Certificate"
export FRAMEWORKS="QtCore QtGui QtPrintSupport QtWidgets"
export BAD_FRAMEWORKS="QtPrintSupport"

# Call itself
deploy.sh SimpleHello.app

With this script, the final output is:

SimpleHello.app/: accepted
source=Developer ID
origin=Developer ID Application: My Certificate (HASH)