Mac – How to rotate inserts in Apple Mac OS preview 7

I've been having the same problem, but I solved it by opening the pdf file in Preview, hitting File > Duplicate, then adding the signature in the newly created file. This corrects the orientation of the file so that Preview can identify lines and you can just click on them with the signature tool (from the Annotate/Edit toolbar) and add your signature.

I came across a binary called "nconvert". I copied these to /usr/local/bin. I then created a simple recursive shell script to go through the folder and subfolders and convert any photo that needs converting.

#!/bin/sh

function recursion {
    if [ $(find . \( -iname "*jpeg" -or -iname "*jpg" \) -maxdepth 1 -type f | wc -l) -gt 0 ]; then
        _fullpath=`pwd`
        echo "Processing $_fullpath"
        echo "Processing $_fullpath" > $HOME/logs/recursive-autorotate-photos.log
        nconvert -jpegtrans exif -overwrite *.jpg
    fi

    for _item in *; do
        if [ -d "$_item" ]; then
            (cd "$_item"; recursion)
        fi
    done
}

if [ ! -z "$1" ]; then
    if [ ! -d "$HOME/logs" ]; then
        mkdir "$HOME"/logs
    fi
    echo "" > $HOME/logs/recursive-autorotate-photos.log

    cd "$1"

    recursion
else
    echo "Usage: recursive-autorotate-photos.sh path-here"
fi

sample: # recursive-autorotate-photos.sh "/Volumes/my-external-disk/photos"

take note of the quotes in the path. if there's a space in the path, there you need to enclosed it in double quotes. I always use double quotes now out of habit.