Around June 2008: Clinton’s first private email server is set up in her house.

080601ApplePowerMcIntoshG4

The Apple Power Macintosh G4 Server (Credit: public domain)

According to the FBI, around 2007, Justin Cooper purchased an Apple OS X server. Cooper is a personal aide to former President Bill Clinton at the time. On February 1, 2008, the domain names clintonemail.com, wjcoffice.com, and presidentclinton.com were registered, but apparently the server that uses them won’t be operational until a few months later. The server is physically located in a house in Chappaqua, New York, where Bill and Hillary Clinton live.

The server consists of an Apple Power Macintosh G4 or G5 tower and an HP printer. According to Cooper, around June 2008, an Apple employee installs the server in the basement of the Chappaqua house. Cooper is the only person with administrative access to the server. However, the Clinton family and their house staff have physical access to it.

Hillary Clinton uses her att.blackberry.net email account as her primary email address until around mid-to-late January 2009 when she will switch to a newly created hdr22@clintonemail.com account hosted on this server. (Federal Bureau of Investigation, 9/2/2016)

Early 2009—March 2015: Sid Blumenthal takes a job at the Clinton Foundation, advises the secretary of state frequently, and promotes the interests of two government contractors.

Sid Blumenthal (Credit: The Guardian)

Sid Blumenthal (Credit: The Guardian)

Sid Blumenthal is paid about $120,000 a year as a full-time employee of the Clinton Foundation. He gets the job in early 2009 at the behest of former President Bill Clinton, who employed him in the White House in the 1990s. He keeps the job until March 2015, the same month that the Clinton email scandal first becomes news.

Blumenthal is a longtime friend of Bill and Hillary Clinton, and a journalist. He appears to have been a private citizen without a security clearance since the 1990s. Yet for the duration of Clinton’s time as secretary of state, and while he is being paid by the Clinton Foundation, he frequently emails her with intelligence information and advice. His foundation job doesn’t seem to have anything to do with any of the foundation’s charitable works.

According to Politico, “While Blumenthal’s foundation job focused on highlighting the legacy of [Bill] Clinton’s presidency, some officials at the charity questioned his value and grumbled that his hiring was a favor from the Clintons, according to people familiar with the foundation.”

In 2011, Blumenthal has a business relationship with two companies, Osprey Global Solutions and Constellations Group, trying to get government contracts to assist US-supported rebels in Libya that year.

After March 2015, Blumenthal will be a paid consultant to American Bridge and Media Matters, two groups supporting Clinton’s presidential campaign that are run by David Brock, an ally of both Clinton and Blumenthal. Politico will later comment, “Blumenthal’s concurrent work for the foundation, the Brock groups, and a pair of businesses seeking potentially lucrative contracts in Libya underscores the blurred lines between her State Department work and that of her family’s charitable and political enterprises.” (Politico, 5/28/2015)

2009: The State Department rolls out an easy way to preserve emails for record keeping, but Clinton’s office elects not to use it and Clinton will later claim she never even heard of it.

Ernie Milner, division chief for SMART Testing and Implementation, and Kevin Gatlin, division chief for SMART Messaging, in the State Department SMART lab in Newington, VA. (Credit: American Diplomacy / University of North Carolina)

Ernie Milner, division chief for SMART Testing and Implementation, and Kevin Gatlin, division chief for SMART Messaging, in the State Department SMART lab in Newington, VA. (Credit: American Diplomacy / University of North Carolina)

In 2009, the first year Clinton is secretary of state, the State Department begins using the State Messaging and Archive Retrieval Toolset (SMART), which allows employees to electronically tag emails to preserve a copy for posterity. This allows employees to easily comply with record keeping regulations, instead of having to print out copies of each email.

Although most of the State Department starts using SMART in 2009; the Office of the Secretary elects not to use the SMART system to preserve emails, partly due to concerns that the system would “allow overly broad access to sensitive materials.” (This quote is from an FBI report, but the name of the official who said it is redacted.)

Representatives from the Executive Secretariat (which includes Clinton’s office) ask to be the last to receive the SMART rollout. Ultimately SMART is never used by the Executive Secretariat Office or Clinton for the rest of Clinton’s four-year tenure.

This leaves printing out each email as the only approved method by which the Clinton or her staff in the Office of the Secretary could preserve emails for record keeping. But when Clinton leaves office in February 2013, she won’t even do that.

Remarkably, when Clinton will be interviewed by the FBI in July 2016, the FBI summary will indicate: “Clinton was not aware how other State [Department] staff maintained their records and was unaware of State’s State Messaging and Archive Retrieval Toolset (SMART).” (Federal Bureau of Investigation, 9/2/2016)

SMART will have security and cost overrun problems for the rest of Clinton’s tenure, and beyond.

January 21, 2009—February 1, 2013: Most State Department officials claim they don’t know Clinton has a private email address or uses a private server.

A sample email of the "H" as it appears in an email sent by Clinton. (Credit: public domain)

A sample address with the “H” as it appears in an email sent by Clinton. (Credit: public domain)

A September 2016 FBI report will indicate that “some Clinton aides and senior-level State [Department] employees were aware Clinton used a personal email address for State business during her tenure [as secretary of state]. Clinton told the FBI it was common knowledge at State that she had a private email address because it was displayed to anyone with whom she exchanged emails. However, some State employees interviewed by the FBI explained that emails from Clinton only contained the letter ‘H’ in the sender field and did not display her email address.”

The report also notes, “The majority of the State employees interviewed by the FBI who were in email contact with Clinton indicated they had no knowledge of the private server in her Chappaqua residence.”

Even Clinton’s closest aides like her chief of staff Cheryl Mills and deputy chief of staff Huma Abedin will claim they didn’t know, though there is evidence that suggests otherwise (Federal Bureau of Investigation, 9/2/2016)

January 21, 2009—February 1, 2013: Hundreds of Clinton’s emails are printed out by a Bill Clinton staffer; he may have a relevant security clearance.

Clinton presents a letter of congratulations and signed photo to Chief Culinary Specialist Oscar Flores during his retirement ceremony aboard the USS Makin Island on April 1, 2010. (Credit: Chief Mass Communication Specialist John Lill / US Navy)

Clinton presents a letter of congratulations and signed photo to Chief Culinary Specialist Oscar Flores during his retirement ceremony aboard the USS Makin Island on April 1, 2010. (Credit: Chief Mass Communication Specialist John Lill / US Navy)

A September 2016 FBI report will mention that the FBI determined “hundreds of emails” were sent by Clinton’s deputy chief of staff Huma Abedin and other State Department staffers to a member of Bill Clinton’s staff so he could print them out for Clinton. His name will be redacted, but he is almost certainly Oscar Flores, because the report will mention that he is a member of the US Navy Reserves, which Flores is at the time.

Some of these emails will later be determined to contain information classified at the “confidential” level, including six email chains forwarded by Abedin and one email chain forwarded by Clinton.

But the FBI will determine that Flores received a security clearance at the “secret” level on October 25, 2007 from the Defense Department. Furthermore, although Flores retires from the US Navy Reserves in September 2010, there is no indication his security clearance is deactivated at that time. (Federal Bureau of Investigation, 9/2/2016)

January 21, 2009—February 1, 2013: Hundreds of classified emails are sent or received by Clinton while she is outside the US, including some to or from President Obama.

Clinton boards the State Department jet with her BlackBerry, destination unknown. (Credit: Andrew Harnik / The Associated Press)

Clinton boards the State Department jet while using her BlackBerry, date and location are unknown. (Credit: Andrew Harnik / The Associated Press)

This is according to a September 2016 FBI report. The report indicates that Clinton and her immediate staff were repeatedly “notified of foreign travel risks and were warned that digital threats began immediately upon landing in a foreign country, since connection of a mobile device to a local network provides opportunities for foreign adversaries to intercept voice and email transmissions.”

Additionally, the State Department has a Mobile Communications Team responsible for establishing secure mobile voice and data communications for Clinton and her team wherever they travel. But even so, Clinton and her staff frequently use their private and unsecure mobile devices and private email accounts while overseas.

The number of Clinton emails sent or received outside the US will be redacted in the FBI report. Although it will mention that “hundreds” were classified at the “confidential” level, additional details are redacted. Nearly all mentions of “top secret” emails are redacted in the report, so it’s impossible to know if any of those are sent while Clinton is overseas.

The report will mention that some emails between Clinton and President Obama are sent while Clinton is overseas. However, the exact number will be redacted. None of these overseas emails between them will be deemed to contain classified information. According to the report, “Clinton told the FBI that she received no particular guidance as to how she should use President Obama’s email address…”

The details of the FBI’s report on Clinton’s July 2016 FBI interview will indicate that Clinton emailed Obama on July 1, 2012 from Russia. However, it is not clear if she sent the email from on the ground or on a plane. (Federal Bureau of Investigation, 9/2/2016)

January 21, 2009—February 1, 2013: Four of Clinton’s top aides frequently use personal email accounts for work matters and then fail to properly archive them.

After Clinton’s email scandal becomes public in March 2015, The State Department will request all work-related emails from four of Clinton’s top aides: Cheryl Mills, Huma Abedin, Jake Sullivan, and Philippe Reines. The emails will be turned over between June and August 2015.

Top left: Cheryl Mills, Top Right: Huma Abedin, Lower left: Jake Sullivan, Lower right: Philippe Reines

Top left: Cheryl Mills, Top Right: Huma Abedin, Lower left: Jake Sullivan, Lower right: Philippe Reines

A department analysis will determine that all four aides frequently used personal email accounts for work matters, although they had government email accounts and sometimes used those as well. The combined work-related personal emails from the four of them will total nearly 72,000 printed pages. One of the four sends and receives 9,585 work emails using a personal account while Clinton is secretary of state, though it isn’t clear which one. That person averages nine work emails from that account per work day.

In May 2016, the department’s inspector general will conclude that, just like Clinton, “these [four aides] failed to comply with department policies… because none of these emails were preserved in department recordkeeping systems prior to [being handed over] in 2015.” (US Department of State, 5/25/2016)

Around February 2009: Clinton allegedly wants to use a iPad in her office but is not allowed to do so; however the iPad won’t be released until one year later.

The first Apple iPad was released in January, 2010. (Credit: public domain)

The first Apple iPad (Credit: public domain)

Around February 2009, the NSA refuses to make a BlackBerry for Clinton that’s secure enough to use in SCIF rooms, citing security concerns. (Highly classified materials can only be read in SCIF rooms, and Clinton’s office in State Department headquarters is a SCIF room.)

According to a September 2016 FBI report, at roughly the same time, Clinton’s executive staff also ask about the possibility of Clinton using an iPad to read her emails in her office. But “this request was also denied due to restrictions associated with the Secretary’s office being in a SCIF.” (Federal Bureau of Investigation, 9/2/2016)

However, the FBI will fail to mention that the iPad won’t actually be announced by Apple until January 2010, and won’t be released until a couple of months after that, making the above claim impossible. (Apple.com, 1/27/2010)

Clinton will buy an iPad and begin using it a couple of months after it comes out, in July 2010.

February 2009: Security officials set up a space near Clinton’s office where she can check her private email account. 

Clinton meets with Supreme Court justice Ruth Bader Ginsburg in her outer office,on January 25, 2012. (Credit: public domain)

Clinton meets with Supreme Court justice Ruth Bader Ginsburg in her outer office, on January 25, 2012. (Credit: public domain)

Clinton’s office in State Department headquarters is a SCIF, which means a secure room, and she’s not allowed to bring her BlackBerry into it. Also, Clinton is unwilling to use a computer to check her emails. But around this time, security officials create a space where she can check her BlackBerry.

In 2016, a State Department official will explain, “There is an area dedicated to supporting the secretary outside but in the immediate vicinity of the secretary’s secure office. Secretary Clinton, as with anyone, could use such non-SCIF spaces to check personal devices.” Apparently, Clinton will use this arrangement for her entire four years as secretary of state. (Fox News, 3/16/2016)

February 13, 2009: It appears the NSA will be able to give Clinton a secure BlackBerry, but this doesn’t happen.

The National Security Agency (NSA) headquarters, in Fort Meade, Maryland. (Credit: public domain)

The National Security Agency (NSA) headquarters, in Fort Meade, Maryland. (Credit: public domain)

Clinton’s chief of staff Cheryl Mills writes in an email to Clinton that a National Security Agency (NSA) official “indicated they could address our BB [BlackBerry] so that BB could work in” secure spaces, “based upon some modifications that could be done.”

Clinton writes back, “That’s good news.”

Eventually, the NSA will decide that creating special BlackBerry modification would be too problematic, so Clinton and her aides will continue to use their unsecure BlackBerrys.

In December 2014, Clinton will turn over more than 30,000 emails, claiming those were all her work-related emails and she deleted the rest. These work-related emails will not be included in those. Instead, the State Department will give them to Judicial Watch in 2016 in response to a Freedom of Information Act (FOIA) lawsuit. Clinton will later inaccurately claim that she didn’t start using her private email account until March, 18, 2009. (The Hill, 3/24/2016) (Judicial Watch, 3/24/2016) (Judicial Watch, 3/17/2016)

March 6, 2009—March 15, 2009: Clinton says she “gets it” about BlackBerry security concerns, but she keeps on using her BlackBerry.

Eric Boswell (Credit: public domain)

Eric Boswell (Credit: public domain)

On March 6, 2009, Assistant Secretary for Diplomatic Security Eric Boswell emails an internal State Department memo with the subject line “Use of BlackBerrys in Mahogany Row.” (“Mahogany Row” is where the seventh floor offices of Clinton and her top aides are.) The memo states, “Our review reaffirms our belief that the vulnerabilities and risks associated with the use of BlackBerrys in the Mahogany Row [redacted] considerably outweigh the convenience their use can add. … Any unclassified BlackBerry is highly vulnerable in any setting to remotely and covertly monitoring conversations, retrieving emails, and exploiting calendars.”

According to an email by another security official nine days later on March 15, Clinton tells Boswell that she read his memo and “gets it.” That email adds, “Her attention was drawn to the sentence that indicates (Diplomatic Security) have intelligence concerning this vulnerability during her recent trip to Asia.”

However, Clinton continues to use her BlackBerry and private server without any apparent changes. (The Washington Post, 3/27/2016)

March 29, 2009: For the first two months Clinton uses her private server for all her emails, it operates without the standard encryption generally used to protect Internet communication.

Clinton meets Chinese State Councillor Dai Bingguo in the Diaoyutai State Guesthouse in Beijing, China, on February 21, 2009. (Credit: Greg Baker / Getty Images)

Clinton meets Chinese State Councillor Dai Bingguo in the Diaoyutai State Guesthouse in Beijing, China, on February 21, 2009. (Credit: Greg Baker / Getty Images)

This is according to a 2015 independent analysis by Venafi Inc., a cybersecurity firm that specializes in the encryption process. Not until this day does the server receive a “digital certificate” that encrypts and protects communication over the Internet through encryption.

The Washington Post will later report, “It is unknown whether the system had some other way to encrypt the email traffic at the time. Without encryption—a process that scrambles communication for anyone without the correct key—email, attachments and passwords are transmitted in plain text.”

A Venafi official will later comment, “That means that anyone could have accessed it. Anyone.” (The Washington Post, 3/27/2016)

Clinton began sending emails using the server by January 28, 2009, but will later claim she didn’t start using it until March 18, 2009—a two-month gap similar to the two-month gap the server apparently wasn’t properly protected. Apparently, she has not given investigators any of her emails from before March 18. (The New York Times, 9/25/2015)

A 2016 op-ed in the Washington Post will suggest that security concerns during Clinton’s February 2009 trip to Asia could have prompted the use of encryption on her server. (The Washington Post, 4/4/2016)

An FBI report released in September 2016 will confirm that encyption only began in March 2009. It states that “in March 2009, [Bill Clinton aide Justin] Cooper registered a Secure Sockets Layer (SSL) encryption certificate at [Bryan] Pagliano’s direction for added security when users accessed their email from various computers and devices.” (Federal Bureau of Investigation, 9/2/2016)

April 3, 2009—February 17, 2011: Cherie Blair, wife of former British Prime Minister Tony Blair, exchanges emails with Clinton at least 37 times.

Cherie Blair (Credit: Neil Hall / Reuters)

Cherie Blair (Credit: Neil Hall / Reuters)

Blair and Clinton communicate like friends, although sometimes politics could be involved, such as when Blair asks Clinton to meet with Qatari royal Sheikha Mozah bint Nasser Al-Missned. (The New York Times, 7/31/2015) (US Department of State) The emails are unusual because Clinton almost never sends or receives emails directly with any foreigners while she is secretary of state. In fact, Clinton claims she only exchanged one email with any foreign official. (The New York Times, 3/10/2015)

April 1, 2010: An NSA official is convicted for possessing a document not marked classified.

Thomas Drake (Credit: H. Darr Beiser / USA Today)

Thomas Drake (Credit: H. Darr Beiser / USA Today)

Whistleblower Thomas Drake, a former senior National Security Agency (NSA) official, is indicted under the Espionage Act for keeping an NSA email printout at home that was not marked as classified. Drake will later plead guilty to a misdemeanor.

In contrast to this case, Clinton and some of her supporters will later claim that she does not face legal jeopardy if the emails on her private server were not explicitly labeled as classified. (The New York Times, 8/8/2015)

July 25, 2010: Clinton invites a US diplomat to discuss communications with foreign ministers with her using her private email address.

100725Montage

Italian Foreign Minister Franco Frattini (top left) (Credit: European Press Agency), Greek Prime Minister George Papandreou (top right) (Credit: Greek Reporter), Spanish foreign minister Miguel Angel Moratinos (lower left) (Credit: 525-gi gazet), Israeli Prime Minister Benjamin Netanyahu (lower right) (Credit: Israel Ministry of Foreign Affairs)

Clinton writes an email to former senator George J. Mitchell (D), who is the US Special Envoy for Middle East Peace at the time. The subject heading is “Here’s my personal email,” and the entire message is “Pls [Please] use this for reply–HRC [Hillary Rodham Clinton].” (US Department of State, 9/30/2015) 

Mitchell replies, “I talked with Frattini again and went over the point again. He said he understands and agrees.” The rest of his email is later redacted because it contains “foreign government information.” “Frattini” is a likely reference to Italian Foreign Minister Franco Frattini.

Clinton replies, “I told Papandreou the same.” “Papandreou” is a likely reference to Greek Prime Minister George Papandreou. (US Department of State, 9/30/2015) 

Mitchell then discusses communicating with “Moratinos,” a likely reference to Spanish foreign minister Miguel Angel Moratinos.

Clinton replies by mentioning a plan to call “Ashton,” a likely reference to the European Union foreign policy chief Catherine Ashton, and “Bibi,” the nickname of Israeli Prime Minister Benjamin Netanyahu. (US Department of State, 9/30/2015) 

It is not clear why Clinton invites Mitchell to discuss such high-level diplomatic communications via her unsecure personal email address. In 2015, J. William Leonard, former director of the US Information Security Oversight Office, will make the general comment, “If a foreign minister just told the secretary of state something in confidence, by US rules that is classified at the moment it’s in US channels and US possession. […] It’s born classified.” (Reuters, 8/21/2015)

November 2010: Clinton writes she doesn’t want “any risk of the personal being accessible” in her emails, contradicting her later claim that her main concern is “convenience.”

The seventeen words that merited a headline by the New Yorker: "Let's get separate address or device but I don't want any risk of the personal being accessible." (Credit: The New Yorker)

The seventeen words that merited a headline by the New Yorker: “Let’s get separate address or device but I don’t want any risk of the personal being accessible.” (Credit: The New Yorker)

Clinton and her deputy chief of staff, Huma Abedin, discuss the fact that Clinton’s emails to other State Department employees are sometimes not being received. Apparently, they are getting discarded as spam because they are coming from an unofficial address.

Abedin tells Clinton in an email that “we should talk about putting you on state email or releasing your email address to the department so you are not going to spam.”

In response, Clinton writes, “Let’s get separate address or device but I don’t want any risk of the personal being accessible.” (US Department of State, 5/25/2016)

In 2016, the New Yorker Magazine will comment that Clinton’s “personal being accessible” comment “seem[s] to confirm what many observers have suspected from the outset: Clinton’s main motive in setting up the email system wasn’t to make it easier for her to receive all her messages in one place, or to do all her business on her beloved BlackBerry; it was to protect some of her correspondence—particularly correspondence she considered private—from freedom-of-information requests and other demands for details, for example, from Republican-run congressional committees.” (The New Yorker, 5/26/2016)

These emails between Clinton and Abedin will not be included in the 30,000 work-related emails that Clinton turns over to the State Department in December 2014, even though they clearly discuss work matters. The State Department will later discover them through other means, most likely from Abedin’s email inbox. (The Associated Press, 5/26/2016)

December 22, 2010: Clinton is told a new rule that all work emails must be preserved.

The National Archives building in Washington, DC. (Credit: public domain)

The National Archives building in Washington, DC. (Credit: public domain)

The National Archives and Records Administration (NARA) issues guidelines to the heads of all federal agencies, including Secretary of State Clinton, stating that all emails and email attachments relating to government business are considered records to be preserved under the Federal Records Act. (The Wall Street Journal, 9/30/2015)