Installing Mac GNU Privacy Guard (GPG)
Posting from: Tucson, AZ
Listening to: Booker T. and the MG's, Hip Hugger
This post is an excruciatingly detailed step-by-step idiot's guide for setting up text/e-mail encryption capability for Mac OS X. I think it's complete now. Everything seems to be up and running. Actually, I still need to try sending an encrypted mail, but other than that everything's working. I'll do that later tonight. I will put a link to this page over on the left side of the page under the Bulletin Board heading after I do that. My new public key is over there, too.
Many, many, many thanks to the folks over at TCF for getting me through this before and now again. If anything here doesn't work, it's probably not their fault but mine for missing something in translation. Use this document at your own risk- I'm not an expert by any means and was just stumbling through this process as a complete encryption newbie with the help of more knowledgeable folks. If you have any questions, feel free to post them here and I'll help if I can (which is not likely, but possible).
1. Open Finder. Click on Applications. From the Applications folder, select File > New Folder and rename the new folder GNU Privacy Guard. From this newly created folder, create five new folders and rename them GnuPG, GPGDropThing, GPGFileTool, GPGKeychain, GPGPreferences, and GPGMail.
2. In your web browser's preferences, turn off the option to open downloaded files automatically. To do this in Safari, select Safari > Preferences > General (tab) and uncheck the option to Open "safe" files after downloading.
3. GNU Privacy Guard: the main program
3a. Download
Go to the Mac GNU Privacy Guard website. Scroll down to the section titled Files. Download the version of GNU Privacy Guard that is compatible with your version of Mac OS X by clicking on the version number link, selecting a site on the next page from which to download, and then clicking the Download link. This will download a file called GnuPG 1.4.3.dmg (file name will be slightly different if you were downloading for a version of OS X other than Tiger). Once the download has begun, use the Back button on your browser to return to the Mac GNU Privacy Guard page.
3b. Verify the file
Go to the Finder, select Applications > Utilities and double-click on Terminal to open a terminal window. At the command prompt, change the directory to the one into which you downloaded the file. The command to change directories is cd followed by the pathname of the directory you want to change to. My file downloaded to the desktop so I used the command cd /Desktop. The prompt will change to reflect the new directory you've changed over to. At the prompt, verify the checksum with the command openssl md5 GnuPG1.4.3.dmg (substitute whatever file name you downloaded if you were downloading for a version of OS X other than Tiger) and hit Return to execute the command. A string of numbers and letters will be returned. Compare this string with the string provided under the corresponding section of the Mac GNU Privacy Guard website. They should be the same. If they are not, do not use the file and instead use the contact the management link under the Files section on the Mac GNU Privacy Guard website to report the discrepancy.
3c. Install
Double-click the disk image file called GNUPG1.4.3.dmg (or other file you downloaded) to open it. It will contain three files. Select and drag them to the folder Applications > GNU Privacy Guard > GnuPG. Double-click the file that ends in .mpkg and follow the instructions to install. (It installs command line tools for which you will not see any icons. You can learn to use the command line tools, but it isn't necessary.)
3d. Cleanup
Delete all associated files EXCEPT the three you put in the folder Applications > GNU Privacy Guard > GnuPG by dragging them to the trashcan in the dock, clicking the trashcan icon, and selecting Empty Trash.
4. GPG Keychain Access: GUI for managing keys
4a. Download
Download GPG Keychain Access by clicking on the version number link, selecting a site on the next page from which to download, and then clicking the Download link. This will download a file called GPG_Keychain_Access.0.7.0.1.zip. Once the download has begun, use the Back button on your browser to return to the Mac GNU Privacy Guard page.
4b. Verify
Return to the terminal window. At the prompt, verify the checksum with the command openssl md5 GPG_Keychain_Access.0.7.0.1.zip and hit Return to execute the command. A string of numbers and letters will be returned. Compare this string with the string provided under the corresponding section of the Mac GNU Privacy Guard website. They should be the same. If they are not, do not use the file and instead use the contact the management link under the Files section on the Mac GNU Privacy Guard website to report the discrepancy.
4c. Install
Double-click the file GPG_Keychain_Access.0.7.0.1.zip. This will generate a folder titled GPG Keychain Access- double-click it to open it. It will contain four files. Select and drag them to the folder Applications > GNU Privacy Guard > GPGKeychain.
4d. Cleanup
Delete all associated files EXCEPT the four you put in the folder Applications > GNU Privacy Guard > GPGKeychain by dragging them to the trashcan in the dock, clicking the trashcan icon, and selecting Empty Trash.
5. GPGFileTool: GUI for encrypting and decrypting files
5a. Download
Download GPGFileTool by clicking on the version number link, selecting a site on the next page from which to download, and then clicking the Download link. This will download a file called GPGFileTool-1.0.2.tar.gz. Once the download has begun, use the Back button on your browser to return to the Mac GNU Privacy Guard page.
5b. Verify
Return to the terminal window. At the prompt, verify the checksum with the command openssl md5 GPGFileTool-1.0.2.tar.gz and hit Return to execute the command. A string of numbers and letters will be returned. Compare this string with the string provided under the corresponding section of the Mac GNU Privacy Guard website. They should be the same. If they are not, do not use the file and instead use the contact the management link under the Files section on the Mac GNU Privacy Guard website to report the discrepancy.
5c. Install
Double-click the file GPGFileTool-1.0.2.tar.gz. This will generate a file ending in .tar and then a folder titled GPGFileTool- double-click it to open it. It will contain two files. Select and drag them to the folder Applications > GNU Privacy Guard > GPGFileTool.
5d. Cleanup
Delete all associated files EXCEPT the two you put in the folder Applications > GNU Privacy Guard > GPGFileTool by dragging them to the trashcan in the dock, clicking the trashcan icon, and selecting Empty Trash.
6. GPGDropThing: opens a window allowing you to encrypt and decrypt text
6a. Download
Download GPGDropThing by clicking on the version number link, selecting a site on the next page from which to download, and then clicking the Download link. This will download a file called GPGDropThing-0.4.3.dmg.gz. Once the download has begun, use the Back button on your browser to return to the Mac GNU Privacy Guard page.
6b. Verify
Return to the terminal window. At the prompt, verify the checksum with the command openssl md5 GPGDropThing-0.4.3.dmg.gz and hit Return to execute the command. A string of numbers and letters will be returned. Compare this string with the string provided under the corresponding section of the Mac GNU Privacy Guard website. They should be the same. If they are not, do not use the file and instead use the contact the management link under the Files section on the Mac GNU Privacy Guard website to report the discrepancy.
6c. Install
Double-click the file GPGDropThing-0.4.3.dmg.gz. This will generate a file called GPGDropThing-0.4.3.dmg- double-click it and a disk image file called GPGDropThing will be generated. It will contain three files. Select and drag them to the folder Applications > GNU Privacy Guard > GPGDropThing.
6d. Cleanup
Delete all associated files EXCEPT the ones you put in the folder Applications > GNU Privacy Guard > GPGDropThing by dragging them to the trashcan in the dock, clicking the trashcan icon, and selecting Empty Trash.
7. GPGPreferences:
7a. Download
Download GPGPreferences by clicking on the version number link, selecting a site on the next page from which to download, and then clicking the Download link. This will download a file called GPGPreferences-1.2.dmg. Once the download has begun, use the Back button on your browser to return to the Mac GNU Privacy Guard page.
7b. Verify
Return to the terminal window. At the prompt, verify the checksum with the command openssl md5 GPGPreferences-1.2.dmg and hit Return to execute the command. A string of numbers and letters will be returned. Compare this string with the string provided under the corresponding section of the Mac GNU Privacy Guard website. They should be the same. If they are not, do not use the file and instead use the contact the management link under the Files section on the Mac GNU Privacy Guard website to report the discrepancy.
7c. Install
Double-click the file GPGDropThing-0.4.3.dmg.gz. This will generate a file called GPGDropThing-0.4.3.dmg- double-click it and a disk image file called GPGPreferences 1.2 will be generated. It will contain one files. Select and drag it to the folder Applications > GNU Privacy Guard > GPGPreferences. From the folder you just dragged it to, double click the file (called GPGPreferences-1.2.pkg) and follow the instructions to install. This will generate a GnuPG icon that appears in the Other section at the bottom of the System Preferences screen (accessible from the Apple menu or the dock).
7d. Cleanup
Delete all associated files EXCEPT the ones you put in the folder Applications > GNU Privacy Guard > GPGPreferences by dragging them to the trashcan in the dock, clicking the trashcan icon, and selecting Empty Trash.
8. Generate a key pair
8a. Go to Applications > GNU Privacy Guard > GPGKeychain and open GPG Keychain Access. You will get a message that says You do not have a private or secret key. Select Generate. Follow the instructions in the Make a new key assistant.
8b. At the Introduction screen select Continue.
8c. For the type of key, select DSA and ElGamal and Continue.
8d. Select a key size (I chose 4096) and Continue.
8e. Decide whether or not you want your key to expire and then Continue.
8f. Enter a full name (which can be fictitious), the e-mail address you wish to use this key in association with, uncheck Use my card from Address Book if you so desire, and then Continue.
8g. Set your passphrase and then Continue. You will need to remember this in order to encrypt/decrypt messages.
8h. Confirm your selections and Continue. Your key will be generated. This could take a while depending on the key size you chose.
9. GPGMail: adds GnuPG support to Apple's Mail
9a. Download
Scroll down to the bottom of the Mac GNU Privacy Guard page to the Links section. Follow the link called GPGMail to another website. Click the link called Download a little way down from the flags. Under the Download section, choose the 10.3 or 10.4 binaries, depending on your OSX version. This will download a file called GPGMail-10.4.dmg (filename will be different for 10.3).
9b. Verify
Return to the terminal window. At the prompt, verify the checksum with the command openssl md5 GPGMail-10.4.dmg and hit Return to execute the command. A string of numbers and letters will be returned. Compare this string with the string provided next to the download link on the GPGMail page. They should be the same. If they are not, do not use the file.
9c. Install
Don't follow the installation instructions on the web page. Instead, double-click the disk image file called GPGMail-10.4.dmg and the double-click the Install GPGMail icon in the .dmg file. From the .dmg file, select and drag the files called CpMac, plistutil, GPGMail.mailbundle, and Install GPGMail to your GPGMail folder. Then double-click the Documentation folder in the .dmg file, and click and drag the English.lproj sub-folder to your GPGMail folder.
9d. Cleanup
Delete all associated files EXCEPT the ones you put in the folder Applications > GNU Privacy Guard > GPGMail by dragging them to the trashcan in the dock, clicking the trashcan icon, and selecting Empty Trash.
Listening to: Booker T. and the MG's, Hip Hugger
This post is an excruciatingly detailed step-by-step idiot's guide for setting up text/e-mail encryption capability for Mac OS X. I think it's complete now. Everything seems to be up and running. Actually, I still need to try sending an encrypted mail, but other than that everything's working. I'll do that later tonight. I will put a link to this page over on the left side of the page under the Bulletin Board heading after I do that. My new public key is over there, too.
Many, many, many thanks to the folks over at TCF for getting me through this before and now again. If anything here doesn't work, it's probably not their fault but mine for missing something in translation. Use this document at your own risk- I'm not an expert by any means and was just stumbling through this process as a complete encryption newbie with the help of more knowledgeable folks. If you have any questions, feel free to post them here and I'll help if I can (which is not likely, but possible).
1. Open Finder. Click on Applications. From the Applications folder, select File > New Folder and rename the new folder GNU Privacy Guard. From this newly created folder, create five new folders and rename them GnuPG, GPGDropThing, GPGFileTool, GPGKeychain, GPGPreferences, and GPGMail.
2. In your web browser's preferences, turn off the option to open downloaded files automatically. To do this in Safari, select Safari > Preferences > General (tab) and uncheck the option to Open "safe" files after downloading.
3. GNU Privacy Guard: the main program
3a. Download
Go to the Mac GNU Privacy Guard website. Scroll down to the section titled Files. Download the version of GNU Privacy Guard that is compatible with your version of Mac OS X by clicking on the version number link, selecting a site on the next page from which to download, and then clicking the Download link. This will download a file called GnuPG 1.4.3.dmg (file name will be slightly different if you were downloading for a version of OS X other than Tiger). Once the download has begun, use the Back button on your browser to return to the Mac GNU Privacy Guard page.
3b. Verify the file
Go to the Finder, select Applications > Utilities and double-click on Terminal to open a terminal window. At the command prompt, change the directory to the one into which you downloaded the file. The command to change directories is cd followed by the pathname of the directory you want to change to. My file downloaded to the desktop so I used the command cd /Desktop. The prompt will change to reflect the new directory you've changed over to. At the prompt, verify the checksum with the command openssl md5 GnuPG1.4.3.dmg (substitute whatever file name you downloaded if you were downloading for a version of OS X other than Tiger) and hit Return to execute the command. A string of numbers and letters will be returned. Compare this string with the string provided under the corresponding section of the Mac GNU Privacy Guard website. They should be the same. If they are not, do not use the file and instead use the contact the management link under the Files section on the Mac GNU Privacy Guard website to report the discrepancy.
3c. Install
Double-click the disk image file called GNUPG1.4.3.dmg (or other file you downloaded) to open it. It will contain three files. Select and drag them to the folder Applications > GNU Privacy Guard > GnuPG. Double-click the file that ends in .mpkg and follow the instructions to install. (It installs command line tools for which you will not see any icons. You can learn to use the command line tools, but it isn't necessary.)
3d. Cleanup
Delete all associated files EXCEPT the three you put in the folder Applications > GNU Privacy Guard > GnuPG by dragging them to the trashcan in the dock, clicking the trashcan icon, and selecting Empty Trash.
4. GPG Keychain Access: GUI for managing keys
4a. Download
Download GPG Keychain Access by clicking on the version number link, selecting a site on the next page from which to download, and then clicking the Download link. This will download a file called GPG_Keychain_Access.0.7.0.1.zip. Once the download has begun, use the Back button on your browser to return to the Mac GNU Privacy Guard page.
4b. Verify
Return to the terminal window. At the prompt, verify the checksum with the command openssl md5 GPG_Keychain_Access.0.7.0.1.zip and hit Return to execute the command. A string of numbers and letters will be returned. Compare this string with the string provided under the corresponding section of the Mac GNU Privacy Guard website. They should be the same. If they are not, do not use the file and instead use the contact the management link under the Files section on the Mac GNU Privacy Guard website to report the discrepancy.
4c. Install
Double-click the file GPG_Keychain_Access.0.7.0.1.zip. This will generate a folder titled GPG Keychain Access- double-click it to open it. It will contain four files. Select and drag them to the folder Applications > GNU Privacy Guard > GPGKeychain.
4d. Cleanup
Delete all associated files EXCEPT the four you put in the folder Applications > GNU Privacy Guard > GPGKeychain by dragging them to the trashcan in the dock, clicking the trashcan icon, and selecting Empty Trash.
5. GPGFileTool: GUI for encrypting and decrypting files
5a. Download
Download GPGFileTool by clicking on the version number link, selecting a site on the next page from which to download, and then clicking the Download link. This will download a file called GPGFileTool-1.0.2.tar.gz. Once the download has begun, use the Back button on your browser to return to the Mac GNU Privacy Guard page.
5b. Verify
Return to the terminal window. At the prompt, verify the checksum with the command openssl md5 GPGFileTool-1.0.2.tar.gz and hit Return to execute the command. A string of numbers and letters will be returned. Compare this string with the string provided under the corresponding section of the Mac GNU Privacy Guard website. They should be the same. If they are not, do not use the file and instead use the contact the management link under the Files section on the Mac GNU Privacy Guard website to report the discrepancy.
5c. Install
Double-click the file GPGFileTool-1.0.2.tar.gz. This will generate a file ending in .tar and then a folder titled GPGFileTool- double-click it to open it. It will contain two files. Select and drag them to the folder Applications > GNU Privacy Guard > GPGFileTool.
5d. Cleanup
Delete all associated files EXCEPT the two you put in the folder Applications > GNU Privacy Guard > GPGFileTool by dragging them to the trashcan in the dock, clicking the trashcan icon, and selecting Empty Trash.
6. GPGDropThing: opens a window allowing you to encrypt and decrypt text
6a. Download
Download GPGDropThing by clicking on the version number link, selecting a site on the next page from which to download, and then clicking the Download link. This will download a file called GPGDropThing-0.4.3.dmg.gz. Once the download has begun, use the Back button on your browser to return to the Mac GNU Privacy Guard page.
6b. Verify
Return to the terminal window. At the prompt, verify the checksum with the command openssl md5 GPGDropThing-0.4.3.dmg.gz and hit Return to execute the command. A string of numbers and letters will be returned. Compare this string with the string provided under the corresponding section of the Mac GNU Privacy Guard website. They should be the same. If they are not, do not use the file and instead use the contact the management link under the Files section on the Mac GNU Privacy Guard website to report the discrepancy.
6c. Install
Double-click the file GPGDropThing-0.4.3.dmg.gz. This will generate a file called GPGDropThing-0.4.3.dmg- double-click it and a disk image file called GPGDropThing will be generated. It will contain three files. Select and drag them to the folder Applications > GNU Privacy Guard > GPGDropThing.
6d. Cleanup
Delete all associated files EXCEPT the ones you put in the folder Applications > GNU Privacy Guard > GPGDropThing by dragging them to the trashcan in the dock, clicking the trashcan icon, and selecting Empty Trash.
7. GPGPreferences:
7a. Download
Download GPGPreferences by clicking on the version number link, selecting a site on the next page from which to download, and then clicking the Download link. This will download a file called GPGPreferences-1.2.dmg. Once the download has begun, use the Back button on your browser to return to the Mac GNU Privacy Guard page.
7b. Verify
Return to the terminal window. At the prompt, verify the checksum with the command openssl md5 GPGPreferences-1.2.dmg and hit Return to execute the command. A string of numbers and letters will be returned. Compare this string with the string provided under the corresponding section of the Mac GNU Privacy Guard website. They should be the same. If they are not, do not use the file and instead use the contact the management link under the Files section on the Mac GNU Privacy Guard website to report the discrepancy.
7c. Install
Double-click the file GPGDropThing-0.4.3.dmg.gz. This will generate a file called GPGDropThing-0.4.3.dmg- double-click it and a disk image file called GPGPreferences 1.2 will be generated. It will contain one files. Select and drag it to the folder Applications > GNU Privacy Guard > GPGPreferences. From the folder you just dragged it to, double click the file (called GPGPreferences-1.2.pkg) and follow the instructions to install. This will generate a GnuPG icon that appears in the Other section at the bottom of the System Preferences screen (accessible from the Apple menu or the dock).
7d. Cleanup
Delete all associated files EXCEPT the ones you put in the folder Applications > GNU Privacy Guard > GPGPreferences by dragging them to the trashcan in the dock, clicking the trashcan icon, and selecting Empty Trash.
8. Generate a key pair
8a. Go to Applications > GNU Privacy Guard > GPGKeychain and open GPG Keychain Access. You will get a message that says You do not have a private or secret key. Select Generate. Follow the instructions in the Make a new key assistant.
8b. At the Introduction screen select Continue.
8c. For the type of key, select DSA and ElGamal and Continue.
8d. Select a key size (I chose 4096) and Continue.
8e. Decide whether or not you want your key to expire and then Continue.
8f. Enter a full name (which can be fictitious), the e-mail address you wish to use this key in association with, uncheck Use my card from Address Book if you so desire, and then Continue.
8g. Set your passphrase and then Continue. You will need to remember this in order to encrypt/decrypt messages.
8h. Confirm your selections and Continue. Your key will be generated. This could take a while depending on the key size you chose.
9. GPGMail: adds GnuPG support to Apple's Mail
9a. Download
Scroll down to the bottom of the Mac GNU Privacy Guard page to the Links section. Follow the link called GPGMail to another website. Click the link called Download a little way down from the flags. Under the Download section, choose the 10.3 or 10.4 binaries, depending on your OSX version. This will download a file called GPGMail-10.4.dmg (filename will be different for 10.3).
9b. Verify
Return to the terminal window. At the prompt, verify the checksum with the command openssl md5 GPGMail-10.4.dmg and hit Return to execute the command. A string of numbers and letters will be returned. Compare this string with the string provided next to the download link on the GPGMail page. They should be the same. If they are not, do not use the file.
9c. Install
Don't follow the installation instructions on the web page. Instead, double-click the disk image file called GPGMail-10.4.dmg and the double-click the Install GPGMail icon in the .dmg file. From the .dmg file, select and drag the files called CpMac, plistutil, GPGMail.mailbundle, and Install GPGMail to your GPGMail folder. Then double-click the Documentation folder in the .dmg file, and click and drag the English.lproj sub-folder to your GPGMail folder.
9d. Cleanup
Delete all associated files EXCEPT the ones you put in the folder Applications > GNU Privacy Guard > GPGMail by dragging them to the trashcan in the dock, clicking the trashcan icon, and selecting Empty Trash.
posted by Kirsten | 4/28/2006 02:22:00 PM
2 Comments:
Thanks for this. I just switched to an intel iMac from a Dell running SUSE Linux and Windows. I had GPG installed and running on both but have had problems getting it up and running on the mac - couldn't even get enigma mail to work with Thunderbird on this darned Mac. Your tutorial was a big help.
You are VERY welcome! It is a big thrill for me that someone actually was able to use that thing. If you have any comments on how I might improve or clarify it, please feel free to post them here.
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