One such "headache" for the Hillary Clinton team comes in the form of questions from a journalist working for Politico, a website dedicated to reporting on political news, campaigns and US Congress.
Included in the recent email dump displaying the contents of John Podesta's communications, are messages between Clinton's chief strategist Joel Benenson and John Podesta himself.
Here, Benenson's so-called strategy is ignorance.
"I'm leaving town but here is this week's headache FYI — ignoring her completely."
In what really is quite a polite email from a journalist requesting a comment from the presidential nominee's strategist on how Hillary Clinton's campaign is going, Benenson informs Podesta that he is just going to ignore it.
All this came about following an email forwarded by communications adviser Mandy Grunwald, who reckons the articles written by the Politco journos are "idiotic."
"They're going to keep writing these idiotic pieces until we give them something to cover," Grunwald wrote to Benenson.
'Crony-Capitalist in Chief'
And with words of frustration, Brent Budowsky, a political blogger and commentator — who loves an email exchange with Podesta — reckoned that HRC (that's what Hillary Clinton's team call her in emails) urgently "needs code of government ethics."
"Let me cut to the chase: HRC should offer the strongest code of ethics of any presidential candidate in modern history.
"I do not believe HRC will ultimately be elected by making comments in Iowa about income inequality while repeated stories flood the media that make her look like the crony-capitalist in chief."
In another email exchange between Budowsky and Podesta, released by WikiLeaks as part of its 25th batch of files, Budowsky gives Podesta the heads up on his next column, raising concerns over a certain member of the House Committee on Ethics.
On 22 February 2016, Budowsky tells Clinton's campaign chair not to raise the issue that Congressman Trey Gowdy is a member of the House Ethics Committee.
This is because the ethics committee at the time, 15 October 2015, was investigating "whether the Benghazi committee is violating rules by using taxpayer money for a partisan enterprise."
And the reason not to draw attention to Trey Gowdy, was because he chairs the Benghazi committee which was "under the microscope for committing unethical acts."
Budowsky's advice was for Podesta to steer clear of raising that issue on the day that "HRC testifies" unless the strategy is "total war," advising that Gowdy should "leave the Ethics Committee in the days before her testimony."
'Ground To A Pulp'
Joel Johnson, ex senior adviser on policy and communications under President Bill Clinton, also pulls no punches in an email to John Podesta in which, not surprising, he offers some advice.
Johnson said former Democrat presidential candidate Bernie Sanders "needs to be ground to a pulp."
"This is no time to run the general. Crush him as hard as you can. Other than that, hope all is well and congrats on Nevada!"
The race to become the 45th President of the United States is entering its final week. Podesta number 25 is just the latest tranche of personal emails leaked by WikiLeaks in the run up to polling day — and it's not expected to be the last.
It's thought there are enough emails to release a new batch every day until US presidential election is held on November 8, 2016.